50 Best Oak Bluffs Vacation rentals on Holiday Lettings - Cottages

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1,234 Vacation rentals

20

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
European-styled cottage is tucked away down a private lane surrounded by private yard with gardens - you’ll feel like you have completely gotten away from it all. The front door opens into a classic Mudroom with an antique wood, stadium bench seat - and then you step in …see more

from $243 / night

$1,700 - $2,500 / week

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from $243 / night

15

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
MVVR EXCLUSIVE: Adorable, pristine beach cottage has spectacular views across the sound, calm water swimming, great area for kayaking. The open kitchen, dining and living areas are enhanced by the wall of windows facing the waterfront and providing gorgeous water views …see more

from $228 / night

$1,590 - $2,740 / week

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from $228 / night

27

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Lovely Summer Home located in Waterview Farms a private community on the outskirts of Oak Bluffs ******* Sengekontacket Pond, ( saltwater in inlet from the North Shore). This special home boasts beautiful views across peaceful meadows to Sengekontacket Pond and the No …see more

from $286 / night

$2,000 - $3,700 / week

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from $286 / night

(2) Excellent 

21

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
Delightful summer cottage. Great family home for relaxing on the large deck, kayaking the lagoon, great play beach on the lagoon for children. The bunk house with two bedrooms is directly behind the main part of the house, about 10 steps across the yard. The views are …see more

from $272 / night

$1,900 - $3,600 / week

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from $272 / night

38

Vacation home with swimming pool in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Oak Bluffs retreat featuring 18 X 30 foot pool, outdoor patio with sectional sofa seating, spacious dining deck and three levels of luxury living. The outstanding home has been professionally decorated by one of the islands premier decorators. This house is privately si …see more

from $1,143 / night

$8,000 - $12,500 / week

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from $1,143 / night

9

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Ask about children
Cute and Cozy guest house with open floor plan in the kitchen, living and alcove sleeping area with queen bed. This cottage is perfect for couples, the owner will consider one additional child. There is a den with futon sofa separate from the main part of the cottage. …see more

from $193 / night

$1,350 - $1,800 / week

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from $193 / night

34

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Tucked away among the shade trees on Martha's Vineyard, this delightful cabin in the woods is ideal for your next family vacation or getaway with a few close friends. This three-bedroom rental is located less than a mile from the top-ranked, semi-private Farm Neck Golf …see more

from $89 / night

$623 / week

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Responds fast!
avg. 40 minutes

from $89 / night

11

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Open, airy contemporary Cape. All newly furnished, three bedrooms, 2 bathrooms. Ceiling fans in all bedrooms. A short 15 minute walk to Oak Bluffs Center and Beach, shopping, and dining. Sidewalks connect to miles of bike paths. \n Amenities and Features include...\n \ …see more

from $229 / night

$1,600 - $2,550 / week

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from $229 / night

27

Vacation home rental

Martha's Vineyard / Oak Bluffs

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Visitors will enjoy this delightful and comfortable four bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. Relax in the breeze with your morning coffee on the front porch and have afternoon drinks on the back patio. Several gathering areas with b …see more

from $429 / night

$3,000 - $5,300 / week

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from $429 / night

29

Home rental in Oak Bluffs

Martha's Vineyard / Oak Bluffs

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
If you are looking for an immaculate, charming, cottage style, yet modern home and close to Oak Bluffs center look no further. This recently updated 3 bedroom, 2 bath home features sunny open living, kitchen and dining areas. Soft seashore color palette throughout adds …see more

from $318 / night

$2,225 - $3,675 / week

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from $318 / night

34

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Outstanding vacation home, centrally located to all three down island town centers and multiple public beaches. Set in the Iron Hill Farm Community of homes this lovely home overlooks picturesque,- Little Duarte pond. Extended families will enjoy the multiple living s …see more

from $429 / night

$3,000 - $6,300 / week

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from $429 / night

33

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful get away yet is just a short drive to town center. The use of coastal colors and upscale furnishings throughout combine to make this gorgeous Oak Bluffs summer home …see more

from $572 / night

$4,000 - $7,500 / week

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from $572 / night

20

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
Waterfront, Seaview Condo # 205 is a corner unit with balcony, spectacular waterviews and has been all newly updated for 2017 season. Perfect in town location just across the street from Inkwell Beach, walk to town center or pick up the bike path just a few hundred yar …see more

from $189 / night

$1,320 - $4,648 / week

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from $189 / night

24

Vacation home rental

Martha's Vineyard / Oak Bluffs

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
This charming recently renovated waterfront home atop the lagoon bluffs boasts spectacular sunsets and panoramic waterfront views of the Lagoon, outer Vineyard Haven Harbor and Cape Cod from patios, living room, dining room and two upstairs bedrooms. Stairs down to priv …see more

from $450 / night

$3,150 - $4,950 / week

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from $450 / night

13

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Little Jaws, the home where the movie Jaws was filmed is a pristine beach cottage. Set in East Chop, this three plus bedroom rental offering features spectacular views, great swimming, kayaking and gorgeous sunsets. Relax on the large and comfortably furnished waterfro …see more

from $529 / night

$3,700 - $5,500 / week

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from $529 / night

24

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Welcome to this wonderful and pristine clean three bedroom 2 bath Cape Style. Centrally located with easy access to town centers and public beaches all within a 15 min drive from the house. Biking enthusiasts will enjoy the easy access to bike trails that lead to both t …see more

from $343 / night

$2,400 - $3,675 / week

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from $343 / night

17

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
10 minute walk to Oak Bluffs center and beach area from this lovely modern vacation home. Enjoy all that the summer community of Oak Bluffs has to offer, quaint shops, fine and family dining, harbor front stroll where you will and array of dining establishments, all wa …see more

from $386 / night

$2,700 - $4,700 / week

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from $386 / night

30

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
Quintessential waterfront home, situated on the north shore of Martha's Vineyard, East Chop Area. Gorgeous cottage vernacular, pristinely maintained and decorated with perfect blend of coastal colors. Private dock and mooring, for those who might wish to bring a boat, …see more

from $500 / night

$3,500 - $8,000 / week

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from $500 / night

19

Vacation home rental

Martha's Vineyard / Oak Bluffs

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Ask about children
Tiny beach cottage, a rare find these days and just perfectly cute. The cottage is located along the waterfront on East Chop Drive, a very desirable area of Oak Bluffs. The porch looks out over the beach and beyond to the Vineyard Sound. Relax on the covered porch a …see more

from $200 / night

$1,400 - $2,500 / week

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from $200 / night

20

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Beautiful, spacious, 4 bedroom 3.5 bath contemporary home set in a quiet lovely community on the outskirts of Oak Bluffs. This home comfortably hosts extended families with multiple living spaces. The main living level features an open concept and hosts a family TV roo …see more

from $422 / night

$2,950 - $4,950 / week

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from $422 / night

13

Vacation home rental

Martha's Vineyard / Oak Bluffs

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
  • Air conditioning
Bright and newly remodeled classic summer cottage. Conveniently located just one mile from Oak Bluffs town center, Ink Well Beach, shops, fine and family dining, historic Flying Horses Carousel, public tennis courts, Bandstand Park and Oak Bluffs Harbor-front area. …see more

from $258 / night

$1,800 - $2,900 / week

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from $258 / night

22

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Recently updated this lovely 4 bedroom, 3 bath contemporary home features an open floor plan in the living and kitchen areas opening to the covered porch and seating area on the front of the house and the deck and patio dining area off the back of the house. The main li …see more

from $329 / night

$2,300 - $4,500 / week

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from $329 / night

15

Home rental in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, along the Oak Bluffs harbor - and all just a short drive or bike ride away. This vacation home looks and feels so comf …see more

from $465 / night

$3,250 - $4,250 / week

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from $465 / night

28

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
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 Dream is in the lovely Hidden Cove neighborhood ad …see more

from $358 / night

$2,500 - $4,400 / week

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from $358 / night

21

Vacation home accommodation

Martha's Vineyard / Oak Bluffs

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Walk to town and beach from this spacious modern home on a beautiful, treed lot. A delightful blend of amenities and charm. Central air conditioning. \n Amenities and Features include...\n \nWalk to Town, Central Air, WiFi …see more

from $486 / night

$3,400 - $4,000 / week

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from $486 / night

20

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
Adorable Waterfront and Beachfront cottage. Immaculately maintained, lots of summer charm, fantastic views of the Vineyard Sound and Lagoon from the large patio area. Stairs lead directly to private, sandy beach, great area for young children and adults. Kayak ent …see more

from $222 / night

$1,550 - $2,725 / week

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from $222 / night

24

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Spacious and attractive waterfront Cape Cod style home - features gorgeous views, central A/C, Wi-Fi and 4 TV's. Two large decks and a screened porch provide wonderful spaces for summer relaxation in which to enjoy the waterviews. Kayaking enthusiasts will enjoy the g …see more

from $352 / night

$2,460 - $3,810 / week

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from $352 / night

24

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Comfort meets convenience at this lovely Martha's Vineyard vacation rental, which features a shared outdoor pool, on-site tennis courts, and all of the home amenities your group could wish for. In addition, the beach is mere minutes away, making this vacation rental per …see more

from $114 / night

$798 / week

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Responds fast!
avg. 40 minutes

from $114 / night

29

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Enjoy one of the most enviable locations on Martha's Vineyard when you stay at this four-bedroom Oak Bluffs home, a beautifully renovated Victorian with a fenced yard, a porch and deck with accommodations for up to 10 guests. This two-level house sits just half a mile …see more

from $276 / night

$1,932 / week

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Responds fast!
avg. 40 minutes

from $276 / night

43

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
The Weku House is a luxury, 5,000 square foot home located in the beautiful town of Oak Bluffs on Martha’s Vineyard. Originally built in the year 2000, this home was fully renovated in 2015. Elegantly decorated with designer furnishings and interior appointments, the m …see more

from $1,379 / night

$9,650 - $15,150 / week

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from $1,379 / night

14

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Lovely cape home, all newly refurnished for 2013. First level features an open floor plan in the Dining, Kitchen and Living area. The tastefully decorated living area features comfortable furnishings and a 36" screen tv. One bedroom with a double bed and a full bath c …see more

from $225 / night

$1,575 - $2,475 / week

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from $225 / night

25

Vacation home rental

Martha's Vineyard / Oak Bluffs

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Adorable waterfront cottage, pristinely maintained throughout the years. Enjoy privacy and views from the spacious deck. 3 minute walk to great sandy lagoon beach - a perfect place for young children to play. Centrally located just 2 miles to either Vineyard Haven or …see more

from $261 / night

$1,825 - $2,550 / week

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from $261 / night

35

Home rental in Oak Bluffs

Martha's Vineyard / Oak Bluffs

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
  • Air conditioning
Privately situated on a hilltop in Sengkontacket, -spacious tri-leve 4000 sq ft contemporary home. This wonderful vacation home has been updated for summer 2015, AC added, freshly painted, new carpeting and hardwood flooring and new furnishings. Set in a wonderful fam …see more

from $365 / night

$2,550 - $5,850 / week

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from $365 / night

(1) Excellent 

17

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Car not necessary
This is an old farmhouse consisting of 2 floors with 3 bedrooms on the second floor and 1 on the first floor. One queen and 3 doubles. A large living room and bath on the first floor. In the kitchen is a Refrigerator, gas stove with oven, a washer and dryer and a dis …see more

from $400 / night

$2,600 / week

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from $400 / night

24

Home rental in Oak Bluffs

Martha's Vineyard / Oak Bluffs

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
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 …see more

from $543 / night

$3,800 - $7,500 / week

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from $543 / night

13

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
Modern two bedrooms, one bath cottage situated at the end of a quiet street. This cozy cottage is Oak Bluffs center and the town beaches. The home has recently been renovated with new comfortable furnishings including linens and mini spit air located about one mile to s …see more

from $214 / night

$1,500 - $2,600 / week

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from $214 / night

27

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
Seaside Cottage Style Vacation Home. Recently renovated. Perfect for extended families. Walk to Oak Bluffs town center, beach across the street and miles of beach side - bike paths begin just a couple of hundred yards from the house. Ocean views from just about al …see more

from $608 / night

$4,250 - $6,750 / week

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from $608 / night

23

Home rental in Oak Bluffs

Martha's Vineyard / Oak Bluffs

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window ac in all rooms and a well equipped modern kitchen. The home is nicely situated in quiet neighborhood, on the outskirts of Oak Bluffs, convenient to all three down island …see more

from $429 / night

$3,000 - $3,475 / week

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from $429 / night

22

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

5 6 7 nights min

  • 5 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
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 …see more

from $297 / night

$2,075 - $3,775 / week

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from $297 / night

18

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. Main living level features a lovely kitchen very well stocked with dining and cook items, main living room with TV and a large sunporch living …see more

from $533 / night

$3,725 - $4,725 / week

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from $533 / night