Martha's Vineyard Vacation Rentals, Homes, & More

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 25

Oak Bluffs Home
5 Bedrooms / 2 Bathrooms / Sleeps 85 BR / 2 BA / Sleeps 8
Home / 5 Bedrooms / Sleeps 8

from

$315

/ night

Email Owner
Bedrooms:5
Bathrooms:2
Sleeps:8
Type:Home
Per night:$315 - $458
Per week:$2,200 - $3,200
Pets allowed:No
Internet:Yes

Renovated beach house in Oak Bluffs with 5 Bedrooms, 2 full baths, Sleeps 8; Large living/dining room, sliding door opens to deck, flagstone picnic area with gas grill, A/C, Washer/Dryer, Free WIFI, Large flat- screen LED TV's with cable service; Located 10- 20 min walk...

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Oceanfront
1 / 15

Oak Bluffs Home
5 Bedrooms / 3.5 Bathrooms / Sleeps 105 BR / 3.5 BA / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

from

$572

/ night

Email Owner
Bedrooms:5
Bathrooms:3.5
Sleeps:10
Type:Home
Per night:$572 - $929
Per week:$4,000 - $6,500
Pets allowed:No
Internet:Yes

This beautiful fully renovated cottage beach house is available for weekly rent. Come enjoy the great ocean views. Sit out on the large front covered porch – enjoy friends, family and great times! Relax to the sights and sounds of the beautiful ocean. House comfortably sleeps ...

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Bedrooms:5
Bathrooms:1
Sleeps:8
Type:Home
Per night:$322 - $500
Per week:$2,250 - $3,500
Pets allowed:No
Internet:No

Penacook 5 Bedroom Cottage - short stroll down one of the nicest streets in Oak Bluffs to the beach in one direction and town center in the other, where you will find shops, eateries, - gourmet and family style, entertainment, the historic Flying Horsed Carousel, and the beautiful...

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Edgartown Massachusetts Vacation Rentals - Home
1 / 10

Edgartown Home
3 Bedrooms / 2 Bathrooms / Sleeps 63 BR / 2 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$250 - $305
Per month:$7,500 - $9,150
Pets allowed:No
Internet:Yes

This home has everything you need for a vacation on Martha's Vineyard. With 1600 square feet of living space, It is a bright airy contemporary charmingly furnished with a sky lighted living room with Cable TV, DVD, phone, fireplace, internet access with WiFi and comfortable furniture....

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Charming Oak Bluffs house
1 / 5

Oak Bluffs Home
3 Bedrooms / 2 Bathrooms / Sleeps 73 BR / 2 BA / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$300

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$300 - $400
Per month:$9,000 - $12,000
Pets allowed:Yes
Internet:Yes

This 3. 5 Bedroom Home With Skylights, 52 Inch Tv, Computer, Internet, Printer, Fax, Is Your Home Away From Home. 1 Mile From Town 1. 5 Mile From Beach And 7 Miles From Airport Is Ideal Location. 2 Sets Of Golf Clubs And 4 Tennis Racquets For Your Use, 3 Cable Tv's, Master...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 10

Oak Bluffs Home
4 Bedrooms / 3 Bathrooms / Sleeps 84 BR / 3 BA / Sleeps 8
Home / 4 Bedrooms / Sleeps 8
(1) Excellent 1 Review

from

$258

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$258 - $400
Per week:$1,800 - $2,800
Pets allowed:No
Internet:Yes

Newer immaculate four bedroom Cape style home located in a quiet area within easy access to town and beaches. The upper level has 2 master suites each with a private bath, one with a jacuzzi tub. Also has high speed internet....

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Visit to Martha's Vineyard

“ Excellent ”
July 12, 2014
Wonderful house. Great location. Fabulous outdoor shower. We had a great experience.
Diane Carr, Florida

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Exterior view
1 / 8

Vineyard Haven Condo
3 Bedrooms / 3 Bathrooms / Sleeps 83 BR / 3 BA / Sleeps 8
Condo / 3 Bedrooms / Sleeps 8
(1) Excellent 1 Review

from

$286

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Condo
Per night:$286 - $429
Per week:$2,000 - $3,000
Pets allowed:No
Internet:Yes

This spacious, contemporary 3BR/3bath townhouse with expansive deck, open floor plan, cathedral ceilings, and central air conditioning is part of a development (60 homes on 108 acres) which includes a pool, 6 tennis courts, duck pond, and private access to Lake Tashmoo and ...

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Nice, Well Appointed Home

“ Excellent ”
August 26, 2014
A group of friends and I stayed at this rental home in August. The house is very nice. You must have a car as this property is in a wooded community that is well over a mile from Main Street in Vineyard Haven where shops and grocery stores are located. In addition, in order to benefit from the outside amentities of this property, it will require a drive to that location as well, with the exception of the tennis courts.The town home is very clean and is modern. There is cable television and wireless internet available. The two bedrooms with en suites are very spacious. There is a bedroom downstairs in the finished basement that has two sets of bunk beds...great for kids not so much for picky adults. There is also a futon in the den area that can be used as a spleeping space...it is small so better suited for one person or children/teens. I wouldn't consider this a true 3 bedroom setup if your have overly picky adults in your group. But definetly is a great option for two families with children/teens. The property also has a great deck for outside entertaining.
Tonya Plear, Brooklyn, NY

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View from Deck
1 / 12

Edgartown Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 84 BR / 2.5 BA / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$143

/ night

Email Owner
Bedrooms:4
Bathrooms:2.5
Sleeps:8
Type:Home
Per night:$143 - $686
Per week:$1,000 - $4,800
Pets allowed:No
Internet:Yes

This charming home is situated in an idyllic private wooded setting on Sengekontacket Pond, one of the largest salt- water ponds on Martha's Vineyard. The deck looks out over Major's Cove to the Audobon Society 1/4 mile across the water and Nantucket Sound a mile away. In the evening,...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 8

Chilmark Home
2 Bedrooms / 1 Bathroom / Sleeps 82 BR / 1 BA / Sleeps 8
Home / 2 Bedrooms / Sleeps 8

from

$79

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:8
Type:Home
Per night:$79 - $229
Per week:$550 - $1,600
Pets allowed:No
Internet:No

Located at end of a dead- end dirt road on 1. 5 acres with tall pines and oaks. Modified saltbox, owner designed & built in 1978 for potential active solar. First floor has a large country kitchen, living room, bathroom with antique claw foot bathtub & w/d, & 2 decks. Second floor...

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cottage front
1 / 7

Vineyard Haven Cottage
2 Bedrooms / 1 Bathroom / Sleeps 62 BR / 1 BA / Sleeps 6
Cottage / 2 Bedrooms / Sleeps 6
(10) Excellent 10 Reviews

from

$258

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Cottage
Per night:$258
Per week:$1,800
Pets allowed:No
Internet:Yes

Lovely, warm inviting cottage in the Historic Village of Vineyard Haven on Martha's Vineyard. Although you are in town, the cottage is quite and set- back from the road and is afforded a lot of privacy with the mature foliage. Walking distance to restaurants, beaches, shops, ...

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The Best!!

“ Excellent ”
July 27, 2015
What a fantastic experience! Everything you need or want in an adorable comfortable cottage! Very private and the owners are THE BEST! What wonderful memories we have of MV! We will be back! It must have been great because I've been home in California for two days now and when I wake up I still think I'm there (sigh). :) Again, Bernadette and Leigh are such wonderful hosts and we had such a terrific time!
Stacy Ferguson, La Habra California USA

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Edgartown Meadows Summer Retreat
1 / 19

Edgartown Home
3 Bedrooms / 2 Bathrooms / Sleeps 63 BR / 2 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6
(2) Excellent 2 Reviews

from

$300

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$300
Per week:$2,100
Pets allowed:No
Internet:No

Family friendly home close to beaches, bike path and many area attractions. Wireless internet connection available. Outdoor deck with gas grill and outdoor shower. Short drive to both Edgartown state beach and south beach as well as Edgartown center. Outdoor basketball hoop,...

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Well located and roomy home in Edgartown Meadows

“ Excellent ”
August 3, 2015
This Vineyard home has large airy rooms, a quick washer and dryer, a responsive landlord, and pleasant surroundings. The location is within easy driving distance of Edgartown, Vineyard Haven, and Oak Bluffs and right down the street from Morning Glory farms. While humbler than some other Island rentals in terms of updates, it certainly met our budget. We enjoyed our stay.
Margaret Ondov, Clarksville, Maryland

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1 / 17

Edgartown Home
3 Bedrooms / 2 Bathrooms / Sleeps 83 BR / 2 BA / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$358

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$358 - $500
Per week:$2,500 - $3,500
Pets allowed:No
Internet:Yes

Close to Wasque Reservation the house faces due West with magnificent sunsets from multiple decks. Property expansive providing large play areas for children. Short walk to Katama Bay and Beach. Short ride to Wasque Reservation and Wasque Beach. Equal short ride to East Beach, within...

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master bedrrom
1 / 7

Edgartown Townhouse
4 Bedrooms / 3.5 Bathrooms / Sleeps 104 BR / 3.5 BA / Sleeps 10
Townhouse / 4 Bedrooms / Sleeps 10
(1) Excellent 1 Review

from

$275

/ night

Email Owner
Bedrooms:4
Bathrooms:3.5
Sleeps:10
Type:Townhouse
Per night:$275
Per week:$1,925
Pets allowed:No
Internet:Yes

31/2 - 4 Bed Rooms Pool And Tennis Available Jacuzzi, Gas Grill And Sheets Dock For Motor Boat Available Bright And Sunny Bunk Beds Added Bonus Wireless............. ......

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Hidden Cove

“ Excellent ”
July 4, 2011
Our trip to Martha's Vineyard was wonderful. We totally enjoyed our stay at the Hidden Cove townhouse. We were on a girlfriends (4) trip and the large triple story townhouse met our needs perfectly. The location was perfect. The townhouse was neat and clean. The neiborhood was extremely quiet. All of the neighbors were kind and helpful when we needed directions. The view was absolutely breath taking! We have decided to go back next year. Hopefully this same property will be available. Thanks again,R. Williams
Renisha Williams, Phoenix AZ USA

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Scanned photos
1 / 16

Vineyard Haven Cottage
4 Bedrooms / 1.5 Bathrooms / Sleeps 94 BR / 1.5 BA / Sleeps 9
Cottage / 4 Bedrooms / Sleeps 9
(3) Very Good 3 Reviews

from

$58

/ night

Email Owner
Bedrooms:4
Bathrooms:1.5
Sleeps:9
Type:Cottage
Per night:$58 - $286
Per week:$400 - $2,000
Pets allowed:Yes
Internet:No

Acorn in the Woods is a 4 bedroom cottage with deck, grill, fireplace, outside shower, washer/drier, cable, hammocks, tire swing, basketball hoop, and occasional wild turkeys. It is a half mile to town and ferry and a half mile to Lake Tashmoo. The three bedrooms consist ...

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Our trip

“ Excellent ”
September 21, 2008
Excellent location and the accommodations met our needs quite well. As we had heard there would be a lot of wild Turkey sightings. There were many.
JR, Spotsylvania, VA

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Cozy Ling Room with twin pullout sofabed
1 / 20

Oak Bluffs Home
2 Bedrooms / 1 Bathroom / Sleeps 42 BR / 1 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$215

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$215
Per week:$1,500
Pets allowed:Yes
Internet:Yes

Great Getaway Cottage with a short walk to town, the harbor, and the Lagoon . A back yard picnic table, BBQ grill, and swing set. About a mile walk or bike ride to Town. The house has hardwood and fir floors throughout and also has air conditioning. This is a great "get away cottage"...

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1 / 9

Edgartown Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 104 BR / 2.5 BA / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$500

/ night

Email Owner
Bedrooms:4
Bathrooms:2.5
Sleeps:10
Type:Home
Per night:$500
Per week:$3,500
Pets allowed:No
Internet:Yes

Charming, nicely furnished 4 bedroom home with lots of outdoor living/ entertaining space( large open deck and cosy covered porch) 2 fireplaces large country kitchen, new appliances 1/4 mile from Morning Glory Farm and across road from bus stop and bike path, yet private. Easy ...

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1 / 24

Chappaquiddick Home
5 Bedrooms / 4 Bathrooms / Sleeps 165 BR / 4 BA / Sleeps 16
Home / 5 Bedrooms / Sleeps 16
Bedrooms:5
Bathrooms:4
Sleeps:16
Type:Home
Per night:$1,000 - $2,143
Per week:$7,000 - $15,000
Pets allowed:Yes
Internet:Yes

Perfect vacation estate with all the amenities needed for family reunions. The home is nestled atop Sampson’s Hill, the highest elevation in Edgartown, where your family and guests can enjoy outdoor activities and gatherings with the benefits of a full size heated pool, tennis,...

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1 / 8

Oak Bluffs Home
4 Bedrooms / 3.5 Bathrooms / Sleeps 104 BR / 3.5 BA / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$500

/ night

Email Owner
Bedrooms:4
Bathrooms:3.5
Sleeps:10
Type:Home
Per night:$500 - $1,429
Per week:$3,500 - $10,000
Pets allowed:No
Internet:Yes

A fully renovated four bedroom home with three and a half baths and separate garage, landscaped lot and a private dock. Dock can accommodate up to a 25 foot motor boat and is accessible to Vineyard Sound. Family room with cable TV, deck, fully equipped kitchen, wood burning stove,...

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Front of Home
1 / 9

Vineyard Haven Home
4 Bedrooms / 1.5 Bathrooms / Sleeps 84 BR / 1.5 BA / Sleeps 8
Home / 4 Bedrooms / Sleeps 8
(2) Excellent 2 Reviews

from

$260

/ night

Email Owner
Bedrooms:4
Bathrooms:1.5
Sleeps:8
Type:Home
Per night:$260 - $300
Per month:$7,800 - $9,000
Pets allowed:No
Internet:Yes

Fall is being booked. Best features: This charming older home has a great location, a very large LR. with hardwood floors and beach stone fireplace, huge enclosed front porch (35' by 14'), sunny upper deck, hot/cold outdoor shower (great for after the beach) and privacy since...

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Spacious, but cozy.

“ Excellent ”
September 19, 2014
Originally our family of 5 was going to spend the week, but vacation times shifted and a pregnancy created the need for maternity leave later in the year so just my son and I ended up going to the Vineyard. We had a wonderful time relaxing, seeing the sights and hanging out on the beaches. There was more than enough space and the deck and the screened in front porch quickly became our favorite parts of the house. The location was great for reaching any part of the island and the house was very well stocked with kitchen appliances, towels and bedding. We would highly recommend this home to friends and family!
Nancy Riley, Northwestern Vermont

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Tisbury Massachusetts Vacation Rentals - Home
1 / 5

Tisbury Home
5 Bedrooms / 4 Bathrooms / Sleeps 95 BR / 4 BA / Sleeps 9
Home / 5 Bedrooms / Sleeps 9
Bedrooms:5
Bathrooms:4
Sleeps:9
Type:Home
Per night:$1,450 - $1,500
Per month:$43,500 - $45,000
Pets allowed:No
Internet:Yes

This sophisticated five- bedroom house is ideally situated. From the quiet and secluded feeling of your waterfront oasis on Hines Point, you’ll be able to walk to town and dine at the island’s legendary restaurants, the Artcliff Diner and The Black Dog. Watch the sailors and...

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1 / 23

Oak Bluffs Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 84 BR / 2.5 BA / Sleeps 8
Home / 4 Bedrooms / Sleeps 8
(1) Excellent 1 Review

from

$572

/ night

Email Owner
Bedrooms:4
Bathrooms:2.5
Sleeps:8
Type:Home
Per night:$572 - $715
Per week:$4,000 - $5,000
Pets allowed:No
Internet:Yes

Newly refurbished, stately 4262 sq ft. home with 4 bedrooms, 2. 5 baths situated within a five minute walk to the center of Oak Bluffs, beaches, and ride/jog to bike trail. Large fenced yard with shared tennis court and patio. Spacious, open 35x45 living room downstairs with ...

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Perfect Location

“ Excellent ”
August 16, 2013
This was the perfect location for my family vacation. We could walk to everything, however, we were far enough that we did not experience a lot of noise or traffic. The home was in mint condition and the homeowner likes it to stay that way. Not recommended for little children or elderly people, there are a lot of stairs and all the main amenities are on the second and third floor. We have teenagers, so they had their own floor. This gave all of us a lot of privacy and space.
Hillary Dunson, Atlanta, GA

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West Tisbury Massachusetts Vacation Rentals - Home
1 / 10

West Tisbury Home
3 Bedrooms / 1.5 Bathrooms / Sleeps 103 BR / 1.5 BA / Sleeps 10
Home / 3 Bedrooms / Sleeps 10

from

$158

/ night

Email Owner
Bedrooms:3
Bathrooms:1.5
Sleeps:10
Type:Home
Per night:$158 - $358
Per week:$1,100 - $2,500
Pets allowed:No
Internet:Yes

This house is a traditional Vineyard saltbox, on a two acre, secluded, beautifully landscaped section of West Tisbury near Lambert's Cove. It has a huge deck, that extends from the south to the west side of the house, with an outdoor shower, and outdoor furniture. It is fully...

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Vineyard Haven Massachusetts Vacation Rentals - Home
1 / 10

Vineyard Haven Home
4 Bedrooms / 4 Bathrooms / Sleeps 144 BR / 4 BA / Sleeps 14
Home / 4 Bedrooms / Sleeps 14

from

$126

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:14
Type:Home
Per night:$126 - $673
Per month:$3,780 - $20,190
Pets allowed:No
Internet:Yes

Beautiful Vineyard home located in the Mink Meadows community of West Chop. This home offers and in- ground swimming pool and lovely yard and deck for relaxing and outdoor dining. The main house has three bedrooms on the 2nd floor with a master en suite bedroom/bathroom. The first...

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Vineyard Haven Massachusetts Vacation Rentals - Home
1 / 7

Vineyard Haven Home
2 Bedrooms / 1 Bathroom / Sleeps 62 BR / 1 BA / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$126

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Home
Per night:$126 - $168
Per month:$3,780 - $5,040
Pets allowed:Yes
Internet:Yes

Wonderful Vineyard cottage located on third green and fourth tee on the Mink Meadows. The house offers and open floor plan and has two bedrooms with a one on the first floor and one on the second floor (accessed by a spiral staircase). The is a sleeper sofa in the living room for ...

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1 / 21

Edgartown Home
11 Bedrooms / 7 Bathrooms / Sleeps 2311 BR / 7 BA / Sleeps 23
Home / 11 Bedrooms / Sleeps 23

from

$850

/ night

Email Owner
Bedrooms:11
Bathrooms:7
Sleeps:23
Type:Home
Per night:$850 - $1,421
Per month:$25,500 - $42,630
Pets allowed:No
Internet:Yes

Grand vacation home. The Captain Morse House, at the corner of Morse and North Water streets, is one of Edgartown's finest homes, it is perfect for your dream vineyard vacation. With 12, 000 Sq. ft. with 2 porches and a large backyard you will have tons of space to entertain and...

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1 / 23

Chappaquiddick Home
10 Bedrooms / 5 Bathrooms / Sleeps 1910 BR / 5 BA / Sleeps 19
Home / 10 Bedrooms / Sleeps 19

from

$900

/ night

Email Owner
Bedrooms:10
Bathrooms:5
Sleeps:19
Type:Home
Per night:$900 - $1,155
Per month:$27,000 - $34,650
Pets allowed:No
Internet:Yes

This is a wonderful old Vineyard summer home on 88 acres of glorious property featuring rolling hills, hiking trails, groomed lawns, woods, private beaches, beach camp, tennis court and basketball back board (proper foot ware required). The perfect get away spot for a large ...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 22

Oak Bluffs Home
8 Bedrooms / 3 Bathrooms / Sleeps 168 BR / 3 BA / Sleeps 16
Home / 8 Bedrooms / Sleeps 16
(2) Excellent 2 Reviews

from

$671

/ night

Email Owner
Bedrooms:8
Bathrooms:3
Sleeps:16
Type:Home
Per night:$671 - $714
Per month:$20,130 - $21,420
Pets allowed:No
Internet:Yes

A true Vineyard classic from 1890, this house retains its authentic charm yet has been thoughtfully renovated and serves the modern day vacationer well. The 8 bedrooms afford plenty of space to accomodate larger family groups for special reunions and vacations. The living room, ...

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Edgartown Massachusetts Vacation Rentals - Home
1 / 15

Edgartown Home
7 Bedrooms / 4 Bathrooms / Sleeps 167 BR / 4 BA / Sleeps 16
Home / 7 Bedrooms / Sleeps 16
Bedrooms:7
Bathrooms:4
Sleeps:16
Type:Home
Per night:$1,715
Per week:$12,000
Pets allowed:No
Internet:Yes

Waterfront, Chappaquiddick home with dock and guest house. Quintessential Vineyard home sleeps 16. Wonderful views of the bay and 400 feet of private sandy beach for swimming, fishing and kayaking. Large old style living spaces, impeccably maintained. Exceptional privacy, yet ...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 22

Chappaquiddick Home
6 Bedrooms / 4 Bathrooms / Sleeps 156 BR / 4 BA / Sleeps 15
Home / 6 Bedrooms / Sleeps 15
Bedrooms:6
Bathrooms:4
Sleeps:15
Type:Home
Per night:$1,714
Per month:$51,420
Pets allowed:No
Internet:Yes

Located at Snow’s Point on Katama Bay with 500 ft. of private, sandy beach & views of the upper harbor. This charming 12 room shingled, Vineyard style house has lovely gardens, lawn, meadows & 40 acres on which to roam. Many extra amenities add to your vacation enjoyment. Furnished...

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1 / 23

Edgartown Home
5 Bedrooms / 5 Bathrooms / Sleeps 155 BR / 5 BA / Sleeps 15
Home / 5 Bedrooms / Sleeps 15

from

$643

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:15
Type:Home
Per night:$643 - $2,071
Per month:$19,290 - $62,130
Pets allowed:No
Internet:Yes

Newly renovated 5 bedroom Katama home with beautiful 18x40 heated gunite pool, blue stone patio and outdoor stone fireplace. The interior boasts all new furnishings with special touches. Additional amenities include: games, coffee maker, ipod dock, outdoor shower, lobster pot,...

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West Tisbury Massachusetts Vacation Rentals - Home
1 / 48

West Tisbury Home
10 Bedrooms / 5 Bathrooms / Sleeps 1510 BR / 5 BA / Sleeps 15
Home / 10 Bedrooms / Sleeps 15
Bedrooms:10
Bathrooms:5
Sleeps:15
Type:Home
Per night:$1,508 - $2,222
Per week:$10,550 - $15,550
Pets allowed:No
Internet:Yes

Located in one of the most pristine and private areas of the island. This understated, elegant, and spacious estate offers large families the ultimate in a vacation home. Magnificent ocean views and sprawling private yard bordered by stone walls and hundred year old trees. Large...

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Edgartown Massachusetts Vacation Rentals - Home
1 / 40

Edgartown Home
7 Bedrooms / 9 Bathrooms / Sleeps 147 BR / 9 BA / Sleeps 14
Home / 7 Bedrooms / Sleeps 14
Bedrooms:7
Bathrooms:9
Sleeps:14
Type:Home
Per night:$3,572 - $3,858
Per week:$25,000 - $27,000
Pets allowed:No
Internet:Yes

South Beach's newest luxury resort compound combining simple elegance with refined decor. Three levels of custom designed rooms offer options for your ever changing lifestyle. Upper Level- "Greatest" of great rooms with screened porch with double sided fireplace. Large "Entertaining"...

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Aquinnah Massachusetts Vacation Rentals - Home
1 / 22

Aquinnah Home
7 Bedrooms / 6 Bathrooms / Sleeps 147 BR / 6 BA / Sleeps 14
Home / 7 Bedrooms / Sleeps 14

from

$857

/ night

Email Owner
Bedrooms:7
Bathrooms:6
Sleeps:14
Type:Home
Per night:$857 - $1,286
Per month:$25,710 - $38,580
Pets allowed:No
Internet:Yes

The surrounding area is a throwback to a different time as there really isn’t much going on except beautiful beaches, extraordinary sunsets, the sound of the waves crashing in the distance as you sit on the deck with the clearest night skies you’ve ever seen. Spacious & well...

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Edgartown Massachusetts Vacation Rentals - Home
1 / 11

Edgartown Home
6 Bedrooms / 6 Bathrooms / Sleeps 146 BR / 6 BA / Sleeps 14
Home / 6 Bedrooms / Sleeps 14
Bedrooms:6
Bathrooms:6
Sleeps:14
Type:Home
Per night:$2,143 - $2,500
Per month:$64,290 - $75,000
Pets allowed:No
Internet:Yes

Reclusive 5. 5 acres in the middle of Cape Poge Bay yet 10 minutes to Edgartown. Main house has 4 water view bedrooms, each with it's own private bathroom. Gourmet kitchen with a convenient 1/2 bath, screened in porches and expansive wrap around deck areas. Open floor plan post ...

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1 / 30

Oak Bluffs Home
7 Bedrooms / 7 Bathrooms / Sleeps 147 BR / 7 BA / Sleeps 14
Home / 7 Bedrooms / Sleeps 14
(1) Excellent 1 Review
Bedrooms:7
Bathrooms:7
Sleeps:14
Type:Home
Per night:$1,000 - $1,357
Per month:$30,000 - $40,710
Pets allowed:No
Internet:Yes

Located on over 1 acre of waterfront property on East Chop, an exclusive area of historic Oak Bluffs, this unique home is perfect for family and friends that want to vacation together while maintaining their privacy. This home allows up to 4 families to stay together in the same...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 30

Oak Bluffs Home
7 Bedrooms / 3 Bathrooms / Sleeps 147 BR / 3 BA / Sleeps 14
Home / 7 Bedrooms / Sleeps 14

from

$679

/ night

Email Owner
Bedrooms:7
Bathrooms:3
Sleeps:14
Type:Home
Per night:$679 - $1,036
Per week:$4,750 - $7,250
Pets allowed:No
Internet:Yes

In Town, walk to beach, tennis and town area. This wonderful family home has a large wrap around porch, 7 bedrooms and sleeps 12- 14. Many areas of this wonderful older home have been updated. Hi Speed Internet. Amenities and Features include... 1 Block to Beach, Wifi Internet,...

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Vineyard Haven Massachusetts Vacation Rentals - Home
1 / 20

Vineyard Haven Home
6 Bedrooms / 2 Bathrooms / Sleeps 146 BR / 2 BA / Sleeps 14
Home / 6 Bedrooms / Sleeps 14
Bedrooms:6
Bathrooms:2
Sleeps:14
Type:Home
Per night:$1,286 - $1,715
Per week:$9,000 - $12,000
Pets allowed:No
Internet:Yes

Summer Compound in a majestic location. Vintage vacation home perfect for large family gatherings. Enjoy sweeping ocean views from the large comfortably furnished veranda. A large screened porch offers seating for up to 16 - a great spot for dinners and sunset views. Stroll across...

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Vineyard Haven Massachusetts Vacation Rentals - Home
1 / 18

Vineyard Haven Home
6 Bedrooms / 3 Bathrooms / Sleeps 146 BR / 3 BA / Sleeps 14
Home / 6 Bedrooms / Sleeps 14

from

$515

/ night

Email Owner
Bedrooms:6
Bathrooms:3
Sleeps:14
Type:Home
Per night:$515 - $858
Per week:$3,600 - $6,000
Pets allowed:No
Internet:Yes

Privacy Views, walk to private beach. Kayak on scenic Aunt Rhoda's pond. Wonderful post and beam family compound. Sleeps 14. 6 bedrooms, 3. 5 baths. An area of the Vineyard few will ever experience yet convenient to town, dining, theaters, golf, galleries, etc... Amenities ...

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1 / 22

Oak Bluffs Home
7 Bedrooms / 3 Bathrooms / Sleeps 147 BR / 3 BA / Sleeps 14
Home / 7 Bedrooms / Sleeps 14

from

$414

/ night

Email Owner
Bedrooms:7
Bathrooms:3
Sleeps:14
Type:Home
Per night:$414 - $643
Per month:$12,420 - $19,290
Pets allowed:No
Internet:Yes

Classic, "Camp Ground" over sized 7 bedroom 3 bath home in a residential neighborhood within easy walking distance to the beach, shops, restaurants, galleries, etc. It offers double master bedrooms (1st and 2nd floor. ) Enjoy rocking on our huge front porch in over sized Georgia...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 18

Oak Bluffs Home
7 Bedrooms / 3 Bathrooms / Sleeps 147 BR / 3 BA / Sleeps 14
Home / 7 Bedrooms / Sleeps 14
Bedrooms:7
Bathrooms:3
Sleeps:14
Type:Home
Per night:$1,750
Per week:$12,250
Pets allowed:No
Internet:Yes

Delightful historic summer cottage sitting on the edge of Harthaven Harbor. Spectacular views of Vineyard Sound from all areas of the home. Private path leads you to a pristine private association beach, perfect for families of all ages. There is also a private dock in front of the...

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Bedrooms:6
Bathrooms:4
Sleeps:14
Type:Home
Per night:$943 - $2,200
Per week:$6,600 - $15,400
Pets allowed:No
Internet:Yes

Outstanding Katama home set on two private acres and featuring summer living at its best. Families will enjoy the large screened porch beautifully furnished opening onto the deck overlooking the pool and large landscaped yard. South Beach is just 1. 2 Miles from this vacation home...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 21

Oak Bluffs Home
5 Bedrooms / 4 Bathrooms / Sleeps 135 BR / 4 BA / Sleeps 13
Home / 5 Bedrooms / Sleeps 13
(1) Excellent 1 Review

from

$371

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:13
Type:Home
Per night:$371 - $471
Per month:$11,130 - $14,130
Pets allowed:No
Internet:Yes

Newly renovated 5 bedroom home just a mile and a half from the center of Oak Bluffs. New hard wood floors throughout as well as updated furnishings and decor. Dining area is extended by a nice sized sunny deck for outdoor dining. Perfect for a large family vacation. Additional amenities...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 22

Oak Bluffs Home
6 Bedrooms / 3 Bathrooms / Sleeps 136 BR / 3 BA / Sleeps 13
Home / 6 Bedrooms / Sleeps 13

from

$422

/ night

Email Owner
Bedrooms:6
Bathrooms:3
Sleeps:13
Type:Home
Per night:$422 - $758
Per week:$2,950 - $5,300
Pets allowed:No
Internet:Yes

This outstanding Oak Bluffs home is undergoing a complete face lift for the 2012 rental season and is sure to please. Spacious and perfect for extended families, featuring multiple attractively furnished living areas and sleeping 13 comfortably. The lower level of the house features...

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Edgartown Massachusetts Vacation Rentals - Home
1 / 20

Edgartown Home
6 Bedrooms / 4 Bathrooms / Sleeps 136 BR / 4 BA / Sleeps 13
Home / 6 Bedrooms / Sleeps 13

from

$643

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:13
Type:Home
Per night:$643 - $714
Per month:$19,290 - $21,420
Pets allowed:No
Internet:Yes

The location of this wonderful vacation home is one of the most popular locations on the Island. It is near South Beach, Public boat launch, and not far from bike trails and the Historic District of Edgartown. It is bright, clean, and a treasure trove of summer fun options - ...

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Edgartown Massachusetts Vacation Rentals - Home
1 / 41
Bedrooms:5
Bathrooms:4
Sleeps:12
Type:Home
Per night:$779 - $2,493
Per week:$5,450 - $17,450
Pets allowed:No
Internet:Yes

Beautiful, newly- built luxury home with central a/c in Katama, just a mile from the infamous blue waters and rolling surf of South Beach. You will appreciate the attention to detail in this custom- built home, designer furnishings, and the expansive bluestone terraces with heated...

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1 / 18

Chappaquiddick Home
7 Bedrooms / 3 Bathrooms / Sleeps 127 BR / 3 BA / Sleeps 12
Home / 7 Bedrooms / Sleeps 12

from

$571

/ night

Email Owner
Bedrooms:7
Bathrooms:3
Sleeps:12
Type:Home
Per night:$571 - $900
Per week:$4,000 - $6,300
Pets allowed:No
Internet:Yes

This wonderful old rambling Vineyard summer home is like a large camp with an eclectic mix of furnishings and antiques. This home is set on 5. 6 acres of yard, fields and woods with a small, private beach. It is the perfect spot for an informal summer escape. Just a five minute ...

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Edgartown Massachusetts Vacation Rentals - Home
1 / 28

Edgartown Home
6 Bedrooms / 5 Bathrooms / Sleeps 126 BR / 5 BA / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

from

$571

/ night

Email Owner
Bedrooms:6
Bathrooms:5
Sleeps:12
Type:Home
Per night:$571 - $1,286
Per month:$17,130 - $38,580
Pets allowed:No
Internet:Yes

New luxury home in Edgartown that offers central air conditioning and a heated pool. Enjoy the open concept living on the first floor with fireplace and large flat screen tv. There is also a master bedroom with private bath which has an amazing soaking tub. The second floor has a ...

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Edgartown Massachusetts Vacation Rentals - Home
1 / 12

Edgartown Home
5 Bedrooms / 4 Bathrooms / Sleeps 125 BR / 4 BA / Sleeps 12
Home / 5 Bedrooms / Sleeps 12
(1) Excellent 1 Review

from

$429

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:12
Type:Home
Per night:$429 - $571
Per month:$12,870 - $17,130
Pets allowed:No
Internet:Yes

Think of peace and serenity as you walk along the pond front or through the wooded trails. Dramatic waterscapes fill the windows. Original art pieces, bathtubs set into wood and whimsical antiques surround you in this Vineyard country home. Enjoy your latest novel on the comfy deck...

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Edgartown Massachusetts Vacation Rentals - Home
1 / 11

Edgartown Home
5 Bedrooms / 4 Bathrooms / Sleeps 125 BR / 4 BA / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

from

$643

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:12
Type:Home
Per night:$643 - $1,000
Per month:$19,290 - $30,000
Pets allowed:No
Internet:Yes

Relax and enjoy this spacious and well maintained family home while over looking nearly 300 acres of conservation land out to South Beach and the Atlantic. This 3, 500 square foot house was architecturally designed for family living - It offers multiple living areas including a ...

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Vineyard Haven Massachusetts Vacation Rentals - Home
1 / 33

Vineyard Haven Home
8 Bedrooms / 3 Bathrooms / Sleeps 128 BR / 3 BA / Sleeps 12
Home / 8 Bedrooms / Sleeps 12

from

$758

/ night

Email Owner
Bedrooms:8
Bathrooms:3
Sleeps:12
Type:Home
Per night:$758 - $929
Per week:$5,300 - $6,500
Pets allowed:No
Internet:No

Waterfront Property with Main and Guest Houses. This great waterfront home has some A/C in the following locations: Main house 1st level 2 queen bedrooms, 2nd level, and guest house. Amenities and Features include... Waterfront, Tashmoo Beachfront, A/CAdditional amenities include:...

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