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Oak Bluffs Vacation Rentals & Cottages - 124 Rentals Available

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 15

Oak Bluffs Home
4 BR / 3 BA / Sleeps 8 4 8 Min stay variesHome / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Beautiful four bedroom home within walking distance to the Oak Bluffs harbor and town. This home has a nice size first floor living room and separate eat in kitchen. The first floor also has a full bathroom with tub and ...

from

$500

/ night

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Antique Cottage. 2nd Floor balcony opened back up. Many updates for 2016!
1 / 20

Oak Bluffs Home
4 BR / 2 BA / Sleeps 10 4 10 Min stay variesHome / 4 Bedrooms / Sleeps 10
4 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Welcome to the Flying Seahorse, an updated, antique beach cottage that is steps from Oak Bluffs Town Beach, has AC (upstairs, downstairs bedroom and living room), beach views from its balcony, a modern kitchen and ...

from

$400

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 21

Oak Bluffs Home
6 BR / 3 BA / Sleeps 10 6 10 Min stay variesHome / 6 Bedrooms / Sleeps 10
6 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
This well maintained, vintage Victorian home is centrally located, yet away from the hustle and bustle of town: just one block from the beach, two blocks from Waban Park and Ocean Park, three blocks from tennis, bac...

from

$571

/ night

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Oceanfront
1 / 14

Oak Bluffs Home
5 BR / 3.5 BA / Sleeps 10 5 10 7 night min stayHome / 5 Bedrooms / Sleeps 10
5 bedrooms 3.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
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 ...

from

$643

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 8

Oak Bluffs Home
4 BR / 3.5 BA / Sleeps 10 4 10 Min stay variesHome / 4 Bedrooms / Sleeps 10
4 bedrooms 3.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
A fully renovated four bedroom home with 3 1/2 baths, family room, landscaped lot and a private beach and dock. Dock can accommodate up to a 25 foot motor boat, located on The Lagoon and is accessible to Vineyard Soun...

from

$867

/ night

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1 / 34

Oak Bluffs Cottage
6 BR / 3.5 BA / Sleeps 12 6 12 7 night min stayCottage / 6 Bedrooms / Sleeps 12
6 bedrooms 3.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
gingerbread cottage, commercial kitchen, nice breezy front porch, public park out front of house

from

$643

/ night

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1 / 23

Oak Bluffs Home
4 BR / 2.5 BA / Sleeps 8 4 8 7 night min stayHome / 4 Bedrooms / Sleeps 8
4 bedrooms 2.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
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 ...
(1)“ Excellent ”(1 review)

from

$643

/ night

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Seating for 4 at the Dining Table
1 / 20

Oak Bluffs Home
2 BR / 1 BA / Sleeps 4 2 4 Min stay variesHome / 2 Bedrooms / Sleeps 4
2 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Microwave • Washer/Dryer
Great Getaway Cottage with a short walk to Circuit Ave, the harbor, and the Lagoon . A back yard w/ picnic table, BBQ grill. About a mile walk or bike ride to Town. The house has hardwood and fir floors throughout and...

from

$114

/ night

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Turn of the century 6br Vineyard Cottagesummertime view
1 / 17

Oak Bluffs Cottage
6 BR / 2 BA / Sleeps 10 6 10 Min stay variesCottage / 6 Bedrooms / Sleeps 10
6 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Waterview - located on the East Chop Vineyard Highlands overlooking Nantucket Sound, Oak Bluffs harbor, Sunset Lake, and 3 acre Washington Park, this charmingly original 1860's Vineyard cottage is an ideal family va...
(3)“ Excellent ”(3 reviews)

from

$267

/ night

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Charming Oak Bluffs house
1 / 5

Oak Bluffs Home
4 BR / 2 BA / Sleeps 7 4 7 4 night min stayHome / 4 Bedrooms / Sleeps 7
4 bedrooms 2 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
This 4 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 Club...

from

$286

/ night

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Outside view of kitchen and sliding glass door out to the deck.
1 / 25

Oak Bluffs Home
5 BR / 2 BA / Sleeps 8 5 8 7 night min stayHome / 5 Bedrooms / Sleeps 8
5 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
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...

from

$314

/ night

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1 / 19

Oak Bluffs Home
7 BR / 3 BA / Sleeps 12 7 12 Min stay variesHome / 7 Bedrooms / Sleeps 12
7 bedrooms 3 bathrooms Sleeps 12
Dishwasher • Microwave • Toaster
Come and relax on the front porch of this lovely Vineyard home. Located in the desirable East Chop area of Oak Bluffs. The first floor has a nice open space with dining area and living room. There is a nice kitchen with ...

from

$357

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 30

Oak Bluffs Home
6 BR / 3 BA / Sleeps 10 6 10 Min stay variesHome / 6 Bedrooms / Sleeps 10
6 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Come and enjoy this beautiful waterfront home on East Chop! The first floor has a wonderful front seasonal porch with views of the Vineyard Sound. There is a large dining table and room to relax and take in the view. Th...

from

$1,429

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 16

Oak Bluffs Home
Studio / 2 BA / Sleeps 6 0 6 7 night min stayHome / Studio / Sleeps 6
Studio 2 bathrooms Sleeps 6
Dishwasher • Microwave • TV (Antenna)
East Chop Beauty, bike or walk to town and beach. This designer home features comfortable and elegant dĂŠcor, central A/C and large lovely yard and flagstone patio. Interior features a large open dining and living ar...

from

$675

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 37

Oak Bluffs Home
6 BR / 4 BA / Sleeps 8 6 8 14 night min stayHome / 6 Bedrooms / Sleeps 8
6 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Amenities and Features include... Farm Neck Waterfront Home, Spectacular Views across Sengekontacket Lagoon, Short Walk to Association Lagoon Beach area for Kayaking. One mile to State Beach, Bike paths at entance to ...

from

$1,429

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 17

Oak Bluffs Home
3 BR / 2 BA / Sleeps 6 3 6 7 night min stayHome / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Amenities and Features include... Additional amenities include: beach chairs, coffee maker, patio table and chairs, lobster pot, washer / dryer, landscaped, outside shower - enclosed, vacuum, outdoor furniture, ...

from

$375

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 18

Oak Bluffs Home
3 BR / 1 BA / Sleeps 7 3 7 7 night min stayHome / 3 Bedrooms / Sleeps 7
3 bedrooms 1 bathroom Sleeps 7
High Speed Internet • Dishwasher • Microwave
Classic vineyard cottage renovated, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. Main living level features a lovely kithcen very well stocked with dining and cook items, a lar...

from

$532

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 15

Oak Bluffs Home
4 BR / 2 BA / Sleeps 8 4 8 Min stay variesHome / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
This is a wonderful vacation house located about a 10 minute walk to town and little further to the town beach. The home was recently renovated and has a nice open floor plan on the main level which has an updated kitche...

from

$357

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 33

Oak Bluffs Home
4 BR / 2 BA / Sleeps 8 4 8 14 night min stayHome / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Historic harborfront home with private dock has been completely renovated and newly furnished, beautifully appointed throughout to reflect summer living on the Vineyard. The large living and dining areas open onto the e...

from

$929

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 28

Oak Bluffs Home
4 BR / 2 BA / Sleeps 8 4 8 7 night min stayHome / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings including a 56' LED television. Summer...

from

$400

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 36

Oak Bluffs Home
4 BR / 4 BA / Sleeps 8 4 8 7 night min stayHome / 4 Bedrooms / Sleeps 8
4 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Oak Bluffs retreat featuring three levels of luxury living, professionally decorated by one of the islands premier decorators This house is privately situated in an enclave of lovely homes. Bike paths at the entrance co...

from

$429

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 23

Oak Bluffs Home
3 BR / 2 BA / Sleeps 6 3 6 7 night min stayHome / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Quietly nestled on quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The interior has open floor plan tha...

from

$471

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 22

Oak Bluffs Home
8 BR / 3 BA / Sleeps 16 8 16 Min stay variesHome / 8 Bedrooms / Sleeps 16
8 bedrooms 3 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
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 ...

from

$671

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 30

Oak Bluffs Home
7 BR / 7 BA / Sleeps 14 7 14 Min stay variesHome / 7 Bedrooms / Sleeps 14
7 bedrooms 7 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
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. T...

from

$1,000

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 22

Oak Bluffs Home
7 BR / 3 BA / Sleeps 14 7 14 Min stay variesHome / 7 Bedrooms / Sleeps 14
7 bedrooms 3 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
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 floo...

from

$414

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 30

Oak Bluffs Home
7 BR / 3 BA / Sleeps 14 7 14 7 night min stayHome / 7 Bedrooms / Sleeps 14
7 bedrooms 3 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
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. Ameni...

from

$679

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 37

Oak Bluffs Home
7 BR / 3 BA / Sleeps 14 7 14 7 night min stayHome / 7 Bedrooms / Sleeps 14
7 bedrooms 3 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Large families looking for a true shore experience will enjoy this delightful, whimsical, large historic summer home with cottage details set on the edge of Harthaven Harbor. The home boasts spectacular views of Vineya...

from

$1,629

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 26

Oak Bluffs Home
5 BR / 4 BA / Sleeps 13 5 13 Min stay variesHome / 5 Bedrooms / Sleeps 13
5 bedrooms 4 bathrooms Sleeps 13
High Speed Internet • Dishwasher • Microwave
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 outdoo...

from

$371

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 23

Oak Bluffs Home
6 BR / 4 BA / Sleeps 12 6 12 Min stay variesHome / 6 Bedrooms / Sleeps 12
6 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Sitting on the "summer porch" (that is what they were called in the days of old) sipping your favorite beverage, strolling the short distant to the water, relaxing around the table, Well equipped kitchen, reading in ...

from

$429

/ night

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 15

Oak Bluffs Home
6 BR / 3 BA / Sleeps 12 6 12 7 night min stayHome / 6 Bedrooms / Sleeps 12
6 bedrooms 3 bathrooms Sleeps 12
Dishwasher • Microwave • TV (Antenna)
Large families looking for a beachfront adventure will love this relaxed waterfront home. Spectacular views from every room and expansive patios stretch the shoreline. Central location offers a 5 minute drive to town, d...

from

$786

/ night

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