Chappaquiddick Vacation Rentals, Homes, & More

1-44 of 44 Chappaquiddick Rentals

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1 / 19
Bedrooms:4
Bathrooms:4
Sleeps:11
Type:Home
Per night:$1,143 - $1,858
Per week:$8,000 - $13,000
Pets allowed:No
Internet:Yes

Situated along Edgartown's inner harbor, this quintessential Vineyard home invites you to relax and watch the glorious sunsets. This well equipped home offers many amenities of modern living including high speed internet. Two kayaks are available for exploring the harbor or Caleb's...

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Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Home
Per night:$191 - $515
Per week:$1,335 - $3,600
Pets allowed:No
Internet:Yes

Located away from the crowds (but only a ten minute drive to the ferry & Edgartown town), this casual, cozy & charming home, with a Guest House attached via a large deck, is in a natural setting is a great spot to escape to. With both bay and ocean beaches close by, you can walk...

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1 / 16

Chappaquiddick Home
5 Bedrooms / 4 Bathrooms / Sleeps 10

Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Home
Per night:$1,143 - $2,286
Per week:$8,000 - $16,000
Pets allowed:No
Internet:Yes

Beautiful and perfectly located home on top of Chappy's Sampson Hill with heated pool, gardens and hot tub, large yard and porches. All beaches and amenities just 1 mile away. Never see traffic or parking jams, your exclusive home is 1 mile to beach. The home centers on old native...

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1 / 20

Chappaquiddick Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$500

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$500 - $715
Per week:$3,500 - $5,000
Pets allowed:Yes
Internet:Yes

The beautiful, sandy, private association beach is the perfect compliment to this well maintained & appointed vintage Vineyard cottage. This adorable home was one of the first to be built along the bluff overlooking the inner harbor on Chappy. Set on two acres, this cottage boasts...

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1 / 13
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$343 - $643
Per week:$2,400 - $4,500
Pets allowed:No
Internet:No

Wonderful, spacious, open & airy contemporary home set on the Wasque plains with great views of Katama Bay & the Atlantic Ocean (walk to both). Spacious kitchen with breakfast counter, cathedral ceilings, skylights, wall to wall carpeting. Large screened porch, open decks. Adjoins...

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Bedrooms:3
Bathrooms:4
Sleeps:8
Type:Home
Per night:$715 - $1,715
Per week:$5,000 - $12,000
Pets allowed:No
Internet:Yes

360 Degree water views from this newly built upscale Chappy home. Situated on top of Manaca Hill overlooking the inner and outer Edgartown Harbors, this three bedroom home is spacious and tastefully decorated. Outdoor living space includes stone fireplace perfect for evening cocktails...

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1 / 12

Chappaquiddick Home
3 Bedrooms / 2 Bathrooms / Sleeps 7

from

$258

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$258 - $429
Per week:$1,800 - $3,000
Pets allowed:Yes
Internet:Yes

Comfortable, open design, home with view of fields and historic farm house, this newer home borders conservation property & walking trails, and is one mile from the ocean beaches. Secluded setting with three bedrooms upstairs, sleeps 6- 8; 2 half baths and one full bath; outdoor...

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1 / 11

Chappaquiddick Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$315

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$315 - $558
Per week:$2,200 - $3,900
Pets allowed:No
Internet:No

Close your eyes and envision a summer in the romantic yesteryears when Chappaquiddick was a remote outpost, yet here was an amazing rural estate, Carriage House and all. Back then one had to be rowed across to this little island from Edgartown, there was no electricity and hand...

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Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$572 - $1,000
Per week:$4,000 - $7,000
Pets allowed:Yes
Internet:Yes

In a private setting, this lovely, classic, vineyard home, with herb & perennial gardens, is set at the edge of a lawn that slopes down to a pond with views of Katama Bay. It is beautifully decorated w/antiques and fine quality furnishings that complement the relaxed, semi- ...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 18

Chappaquiddick Home
3 Bedrooms / 2 Bathrooms / Sleeps 5

“ Excellent ”1 Review

from

$200

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:5
Type:Home
Per night:$200 - $315
Per week:$1,400 - $2,200
Pets allowed:Yes
Internet:Yes

This is a lovely home on Chappaquiddick that was developed over the years to accommodate multiple generations and be the center of family vacation fun while maintaining its original charm. Like many of the original Chappaquiddick houses the focus is on the family areas. It has a spectacular...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 15

Chappaquiddick Home
3 Bedrooms / 3 Bathrooms / Sleeps 5

from

$850

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:5
Type:Home
Per night:$850
Per week:$5,950
Pets allowed:No
Internet:No

Exceptional home on Chappaquiddick. This three bedroom home has incredible waterviews from just about every room. Walk to private beach or a short distance to Wasque. NOTE:Please go to the "ISLAND INFO" link on our website and click on "Chappaquiddick" for additional IMPORTANT information...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 29
Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Home
Per night:$1,000 - $2,143
Per week:$7,000 - $15,000
Pets allowed:No
Internet:Yes

Tucked away on top of Sampson's Hill, this Contemporary Chappy Compound features a Main House with three levels of living and entertaining spaces - - including four screened porches and two media areas - - a separate Carriage House with three bedrooms, a large private yard and...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 22

Chappaquiddick Home
10 Bedrooms / 5 Bathrooms / Sleeps 19

from

$700

/ night

Email Owner
Bedrooms:10
Bathrooms:5
Sleeps:19
Type:Home
Per night:$700 - $1,485
Per week:$4,900 - $10,395
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 footware required). The perfect get away spot for a largegathering...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 18

Chappaquiddick Home
6 Bedrooms / 4 Bathrooms / Sleeps 16

Bedrooms:6
Bathrooms:4
Sleeps:16
Type:Home
Per night:$1,143 - $1,715
Per week:$8,000 - $12,000
Pets allowed:Yes
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....

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 16

Chappaquiddick Home
6 Bedrooms / 2 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$377

/ night

Email Owner
Bedrooms:6
Bathrooms:2
Sleeps:12
Type:Home
Per night:$377 - $525
Per week:$2,635 - $3,675
Pets allowed:No
Internet:Yes

This lovely old farm house located on 88 wonderful acres is full of charm. This property has lawns, beaches, rolling hills, woodlands and hiking trails. The shared private tennis courts and basketball hoop (proper foot ware required). A stroll away is the sandy beach and a beach...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 19

Chappaquiddick Home
6 Bedrooms / 5 Bathrooms / Sleeps 12

Bedrooms:6
Bathrooms:5
Sleeps:12
Type:Home
Per night:$1,000 - $2,286
Per week:$7,000 - $16,000
Pets allowed:No
Internet:Yes

It is located atop Sampson’ s Hill being the highest elevation in Edgartown. The house is an upside down house consisting of three levels with the top level being the shared living quarters consisting of the living room, dining area, and kitchen giving way to a spectacular...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 17

Chappaquiddick Home
4 Bedrooms / 2 Bathrooms / Sleeps 8

from

$172

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$172 - $343
Per week:$1,200 - $2,400
Pets allowed:Yes
Internet:Yes

Abutting acres of conservation land and miles of walking trails nearby, this property affords the feelings of privacy and space. The house, Sassafras, is perfect for Chappy, with a front to back screened porch to wile away the summer days, to dine al fresco or to play a friendly...

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Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$215 - $386
Per week:$1,500 - $2,700
Pets allowed:No
Internet:Yes

Set among the treetops on Chappaquiddick's highest point with lovely distant views of the ocean and Nanctucket from most windows and the deck/porch. This informal summer home is a perfect vacation spot. It has an open, light and airy design. The mix of older and new furnishings and...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 11
Bedrooms:1
Bathrooms:2
Sleeps:6
Type:Home
Per night:$258 - $408
Per week:$1,800 - $2,850
Pets allowed:No
Internet:No

Set on a hill approximately 25 yards from the Main house (see #733) this spacious, reverse Contemporary "Guest House" is the perfect summer getaway home. The interior is beautifully designed and decorated with water views from every room. The glass sliders on both levels open to ...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 18

Chappaquiddick Home
5 Bedrooms / 3 Bathrooms / Sleeps 10

from

$715

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:10
Type:Home
Per night:$715
Per week:$5,000
Pets allowed:No
Internet:Yes

Charming beachhouse, newly renovated and expanded in 2012. Elegant and simple all at the same time! Many rooms and open deck overlook Edgartown Harbor from which one may enjoy stunning sunsets. Tennis at private court on property and ocean swimming at private beach a short walk ...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 19

Chappaquiddick Home
7 Bedrooms / 3 Bathrooms / Sleeps 12

from

$465

/ night

Email Owner
Bedrooms:7
Bathrooms:3
Sleeps:12
Type:Home
Per night:$465 - $858
Per week:$3,250 - $6,000
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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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 16
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$286 - $500
Per week:$2,000 - $3,500
Pets allowed:No
Internet:Yes

From the second story spacious living area and multiple decks of this wonderful contemporary home you can look across the Wasque Plains, the beach (walking distance! ) and the dunes to a 180 degree spectacular water view of the Atlantic and Katama Bay. It is newly renovated and ...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 10

Chappaquiddick Home
2 Bedrooms / 1 Bathroom / Sleeps 6

from

$261

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Home
Per night:$261 - $378
Per week:$1,825 - $2,640
Pets allowed:No
Internet:Yes

Situated with two other houses on a wonderful, 88 acre, waterfront estate of rolling hills and woods with hiking trails, this secluded "Artist's Barn" has a 2 story living room with oak beams, fieldstone fireplace and sliding glass doors overlooking the low deck. A long sweeping...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 12

Chappaquiddick Home
4 Bedrooms / 2 Bathrooms / Sleeps 8

from

$215

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$215 - $343
Per week:$1,500 - $2,400
Pets allowed:No
Internet:No

This rambling summer cottage is located in a private setting down a country road and is wonderful spot to spend those lazy, hazy days of summer. It is casual in feel, but it is well equipped and comfortable. The walk to the beach is about 10 mins down the sandy driveway. There is...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 18

Chappaquiddick Home
6 Bedrooms / 4 Bathrooms / Sleeps 10

from

$786

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:10
Type:Home
Per night:$786 - $1,143
Per week:$5,500 - $8,000
Pets allowed:No
Internet:Yes

This home has been kept in excellent condition, yet still retains a New England colonial/island feel. The house sits on 12 secluded acres with breathtaking views of Katama Bay and the southern shore. It is a waterfront home with 570 feet of private beach on Katama Bay. The distance...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 22

Chappaquiddick Home
3 Bedrooms / 2 Bathrooms / Sleeps 7

from

$408

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$408 - $429
Per week:$2,850 - $3,000
Pets allowed:No
Internet:Yes

Beautifully maintained three bedroom saltbox with central air conditioning. Enjoy the outdoors in this large yard with porch, patio and deck. Additional amenities include: beach chairs, games, coffee maker, lobster pot, food processor, cooler, cd player, wine glasses, beach...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 12
Bedrooms:3
Bathrooms:1
Sleeps:7
Type:Home
Per night:$115 - $172
Per week:$800 - $1,200
Pets allowed:No
Internet:No

This informal Chappy Cottage is located in a wooded area about midway between the Cape Pogue Wildlife Refuge and the Wasgue Reservation, both of which have glorious hiking trails and beaches (there is a small entry fee). It has easy access to the road that leads to the Chappy ferry....

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 25

Chappaquiddick Home
5 Bedrooms / 3 Bathrooms / Sleeps 8

from

$372

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:8
Type:Home
Per night:$372 - $772
Per week:$2,600 - $5,400
Pets allowed:No
Internet:Yes

Sitting atop Manaca Hill, this Chappy compound enjoys sweeping water views over Edgartown Harbor on out to Cape Pogue. The Chappy Beach House features an upside down layout with living spaces on the second floor designed to take advantage of the water views. The Living Area has a...

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Bedrooms:5
Bathrooms:3
Sleeps:8
Type:Home
Per night:$372 - $772
Per week:$2,600 - $5,400
Pets allowed:No
Internet:Yes

Few homes have a setting like this one! It is high on a hill with magnificent views of Edgartown, Outer Harbor, & Cape Cod from all rooms. It is light & airy and has a sandy, Association beach on the Outer Harbor. It is a and well maintained and attractively decorated home with...

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Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$186 - $500
Per week:$1,300 - $3,500
Pets allowed:No
Internet:Yes

This home has expansive views of Katama Bay and a salt water marsh. A five minute walk from the water this well designed home is clean and attractively decorated. A family room makes it ideal for a family with children. Fishing, biking, walking, birding or just relaxing are all...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 15

Chappaquiddick Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$300

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$300 - $408
Per week:$2,100 - $2,850
Pets allowed:No
Internet:Yes

This Chappy beach house enjoys Edgartown Harbor water views out to Cape Pogue from its perch on Manaca Hill. The Manaca Hill Beach Getaway is designed to enjoy the water views from its second story Great Room with open Living and Dining spaces, vaulted ceiling, Gourmet Kitchen, ...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 12

Chappaquiddick Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$158

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$158 - $250
Per week:$1,100 - $1,750
Pets allowed:No
Internet:Yes

Charming Chappaquiddick cottage with distant views of Katama Bay. Relax on the deck after a day at the beach - Katama Bay is only 300 yards away! Additional amenities include: wood stove, coffee maker, pillows, food processor, fan(s), tennis court, ceiling fan(s), ironing...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 22

Chappaquiddick Home
4 Bedrooms / 2 Bathrooms / Sleeps 10

“ Excellent ”5 Reviews

from

$200

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Home
Per night:$200 - $425
Per week:$1,400 - $2,975
Pets allowed:Yes
Internet:Yes

Spend your vacation in a nature preserve like setting on 57 acres of fields and woods with a long sandy beach at its border. Fresh and salt water ponds, wild flowers, deer, otter, clams, blueberries in season. This wonderful, well maintained 240 year old restored cape, with...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 21

Chappaquiddick Home
6 Bedrooms / 3 Bathrooms / Sleeps 9

from

$315

/ night

Email Owner
Bedrooms:6
Bathrooms:3
Sleeps:9
Type:Home
Per night:$315 - $458
Per week:$2,200 - $3,200
Pets allowed:Yes
Internet:Yes

Vacation on a Beautiful Farm, with acres of field and access to over 100 acres of conservation land and trails. Privacy and open space all in one, with fields and woods, wildflowers and only 1 mile to the ocean beach; includes full access to a members only beach on Edgartown’...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 16

Chappaquiddick Home
3 Bedrooms / 1 Bathroom / Sleeps 6

“ Excellent ”3 Reviews

from

$143

/ night

Email Owner
Bedrooms:3
Bathrooms:1
Sleeps:6
Type:Home
Per night:$143 - $222
Per week:$1,000 - $1,550
Pets allowed:Yes
Internet:Yes

This former workshop on Tom's Neck Farm, has been converted to a wonderful rustic cottage decorated with old farm tools. It sits on 70 acres of land with woods, fields, rolling hills, walking trails, clamming pond and a long, glorious sandy beach. Wildflowers and wildlife abound....

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Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$172 - $243
Per week:$1,200 - $1,700
Pets allowed:Yes
Internet:Yes

Located just off Wasque Road this comfortable, well maintained home lends itself to a relaxed, informal vacation experience. It is just minutes from all of Chappaquiddick's wonderful beaches! The flat yard lends itself to those wonderful summer pastimes like badminton, whiffle...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 13
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$215 - $315
Per week:$1,500 - $2,200
Pets allowed:No
Internet:Yes

One of those wonderful "Chappy" summer homes, this one is a reverse design with glorious waterviews over the end of Katama Bay to the ocean beyond. As it faces West the sunsets can be breathtaking! It is on a short, dead end dirt road with only a scattering of other houses in the...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 16

Chappaquiddick Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

“ Excellent ”1 Review

from

$358

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$358 - $858
Per week:$2,500 - $6,000
Pets allowed:No
Internet:Yes

In a lovely, rural setting on the island of Chappaquiddick, this is a well appointed home with a large country kitchen that flows to an inviting screened porch and spacious living area. Property abuts and has lovely views of Cape Pogue Bay - great for all types of recreational ...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 12

Chappaquiddick Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$243

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$243 - $743
Per week:$1,700 - $5,200
Pets allowed:No
Internet:Yes

Location... Location... Location! ! ! Destinctive- spotless contemporary home. The home is a reverse design to take advantage of the beautiful water views. The bedrooms are on the first floor and the main living area (for maximum views) - kitchen, living room, dining room and ...

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Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$143 - $343
Per week:$1,000 - $2,400
Pets allowed:Yes
Internet:No

Wonderful, informal cottage style home with eclectic furnishings overlooking large tidal salt pond - great for fishing and clamming. Barrier beach and ocean within a 10 minute walk. Nice first floor open living area and a second floor sitting area open onto the deck. Relaxing water...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 4
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

This historic colonial sits on a hill overlooking Katama Bay, with sweeping water views from Edgartown Harbor to Norton Point and the south shore. A short walk across the front yard lands you on the shores of your own private 625- foot beach on Katama Bay. While maintaining its old...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 17

Chappaquiddick Home
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$300

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$300 - $343
Per week:$2,100 - $2,400
Pets allowed:No
Internet:Yes

Tucked away in the prestigious North Neck area of Chappy, this pair of coastal- styled cottages have been recently renovated throughout. The Main Cottage houses the shared living spaces, including an open Living and Dining Area with vaulted ceiling and fireplace, framed by a west-...

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Chappaquiddick Massachusetts Vacation Rentals - Home
1 / 16
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$229 - $400
Per week:$1,600 - $2,800
Pets allowed:No
Internet:Yes

This beautifully built contemporary sits just off Wasque Road on a wooded lot with a lovelygarden gracing the entry to the house. The entry hall grants you access to all three bedrooms and the screened porch and open terrace. The attractive second floor living area is open in design...

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