50 Best Oak Bluffs Vacation rentals on Holiday Lettings - Cottages

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130 Vacation rentals

(3) Very Good 

18

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
Our comfortable, reverse contemporary home has 2 bedrooms on the first floor (one with a full size bed and one with a twin), a 3/4 bath with shower, as well as a family room with a fold-out futon couch. Upstairs on the second floor, our home has an open design with a br …see more

from $243 / night

$1700 - $2000 / week

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from $243 / 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

$2600 / week

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from $400 / night

15

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Come and let your cares float away as you relax on the enormous first-floor front porch or second-floor open deck of this charming 100+-year-old home looking out onto the beautiful Nantucket Sound. The home is sunny, bright and spacious and has a relaxed elegance with a …see more

from $643 / night

$4500 - $5200 / week

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from $643 / night

11

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
Walk to Oak Bluffs town center, ferry or Inkwell Beach from this beach-chic recently renovated and adorable cottage. Upon entering you are greeted with an open floor plan in the living kitchen and dining areas. The living room is tastefully and comfortable furnished and …see more

from $225 / night

$1575 - $2300 / week

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from $225 / night

(1) Very Good 

21

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
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, backetball and a playground and four blocks from town. Enj …see more

from $571 / night

$4000 - $10500 / week

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from $571 / 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 famil …see more

from $429 / night

$3000 - $6300 / week

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from $429 / night

(1) Very Good 

22

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
Walk to town from this meticulously maintained, large & airy, 3 bedroom, 3 full bathroom vacation getaway, located on a beautiful 1/4 acre lot on a quiet street. Watch your troubles sail away while relaxing on the large farmer's porch with your favorite summer beverage, …see more

from $143 / night

$1000 - $3250 / week

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from $143 / 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. Amenities and Features include... Wal …see more

from $250 / night

$1750 - $2600 / week

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from $250 / night

22

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 $414 / night

$2900 - $7500 / week

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from $414 / night

(3) Excellent 

14

Vacation home rental

Martha's Vineyard / Oak Bluffs

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
Classic & charming, turn of the century "campground" home situated on a 4,400 sq. ft. corner lot just a few minutes walk from the beach & town. Spacious & light rooms w/ some intimate spaces, a formal dining room, hardwood & pine floors, and a sweet porch all blend into …see more

from $172 / night

$1200 - $3800 / week

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from $172 / night

19

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 $304 / night

$2125 - $3575 / week

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from $304 / night

18

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Four bedroom Oak Bluffs home located in the Waterview Farm area of Oak Bluffs. Adjacent to Farm Neck Golf & Tennis. Access to Sengekontacket pond. Great for kayaking and canoeing. Large house great for an extended family or two small families. The first floor has an …see more

from $314 / night

$2200 - $3301 / week

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from $314 / night

(3) Excellent 

22

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
This bright and charming 3 bedroom, 1.5 bath house rests outside downtown Oak Bluffs. The house boasts 3 bedrooms, 1.5 baths, an open living room/kitchen combination, 2 decks and an outside eating area. The first floor bedroom contains a full sized bed. A half bat …see more

from $250 / night

$1250 - $2000 / week

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from $250 / night

24

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
Custom built with extraordinary attention to detail. Located on Lagoon Pond with panoramic views up the lagoon. Large comfortably furnished deck and screened porch with dining create a most relaxing atmosphere overlooking the water. Luxury features throughout the house …see more

from $836 / night

$5850 - $12450 / week

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from $836 / 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 cottage renovated, 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, a large sunporch living area and 2nd living area with lar …see more

from $533 / night

$3725 - $4625 / week

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from $533 / night

18

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
Note: This home will have all new furnishings, beds and decor items for summer 2017. The house is being completely painted and all new hardwood floors are being added to areas where carpeting may appear in the current photos. Current photos are of furnishings from previ …see more

from $429 / night

$3000 - $6300 / week

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from $429 / night

22

Vacation home rental

Martha's Vineyard / Oak Bluffs

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Ask about children
  • Air conditioning
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 h …see more

from $422 / night

$2950 - $5300 / week

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from $422 / night

21

Home rental in Oak Bluffs

Martha's Vineyard / Oak Bluffs

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
Sea Glass Cottage Martha's Vineyard Vacation Rentals Sleeps 6. Completely renovated, this charming East Chop cottage will allow its guests to experience all the comforts of modern luxury living combined with the historical splendor of many reclaimed antique furniture pi …see more

from $271 / night

$1900 - $3350 / week

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from $271 / night

13

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
  • Air conditioning
Families are sure to enjoy this cozy home with nautical inspired decor. The main living level offers a spacious living and dining area with cathedral ceiling cooled by window AC. and a neat well equipped kitchen with pass through window. The kitchen opens onto a spaciou …see more

from $197 / night

$1375 - $2075 / week

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from $197 / night

12

Home rental 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
Charming Gingerbread Cottage located in the Tabernacle area of Oak Bluffs. A short stroll brings you to Oak Bluffs Center with shops, family and fine dining, harbor area, bandstand park, and Ink Well Beach. Recently updated, this house features a modern eat in kitchen o …see more

from $483 / night

$3375 - $4375 / week

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from $483 / 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. The …see more

from $261 / night

$1825 - $2925 / week

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from $261 / night

16

Home rental in Oak Bluffs

Martha's Vineyard / Oak Bluffs

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
This house, built in 1865 it is a unique Victorian home, wonderful for family gatherings. The location is ideal - it sits at the heart of Ocean Park, with the closest access to Circuit Avenue of any of the homes on the Park. The home was recently renovated, including ce …see more

from $1057 / night

$7400 - $16400 / week

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from $1057 / night

22

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 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

$2075 - $3775 / week

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from $297 / 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 com …see more

from $225 / night

$1575 - $2375 / week

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from $225 / night

18

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Wonderful, spacious, lovingly maintained and attractive home in exclusive setting - family room with fireplace, large formal living room with fireplace, master bedroom with full private bath. Large kitchen and dining area that opens onto wonderful deck. Association tenn …see more

from $286 / night

$2000 - $3900 / week

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from $286 / night

9

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
Amenities and Features include... Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, food processor, washer / dryer, cd player, landscaped, outside sh …see more

from $361 / night

$2525 / week

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from $361 / 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 s …see more

from $258 / night

$1800 - $3500 / week

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from $258 / 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
MVVR EXCLUSIVE: Custom crafted tri-level, this beautiful sun filled home features, spacious open living spaces, hardwood floors throughout, sleeps 8 with 2 King Masters en-suite, guest king bedroom and semi-private Alcove sleeping area on the 2nd level ( see photo 23) E …see more

from $429 / night

$3000 - $6601 / week

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from $429 / 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 and t …see more

from $247 / night

$1725 - $2225 / week

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from $247 / night

17

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
For those who love an in-town location this area known as the Campground with the historic Tabernacle is the ideal location. The sweet and colorful cottage is pristinely maintained by the owner. Rockers line the porch for your outside enjoyment. The main level hosts the …see more

from $286 / night

$2000 - $2700 / week

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from $286 / night

(2) Very Good 

17

Home rental in Oak Bluffs with golf nearby

Martha's Vineyard / Oak Bluffs

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Newly renovated home across the street from the lagoon and sailing camp! This home features, new stainless steel appliances, granite counter tops with an island. Five minutes away from town and beaches this property is perfectly located. The main floor has central air, …see more

from $200 / night

$1900 - $3301 / week

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from $200 / night

11

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
A new Cape style residence situated on a wooded lot near bike path and just a short ride to town center and ferry. This home features an open design with a bright kitchen/dining/living area with hardwood floors, den and full bath on the first floor. Sliders in the dinin …see more

from $157 / night

$1100 - $2500 / week

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from $157 / night

10

Home rental in Oak Bluffs

Martha's Vineyard / Oak Bluffs

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
This sweet, little (it's priced accordingly!)cottage is all about convenience. It is within walking distance to the center of Oak Bluffs and two town beaches. The interior of the cottage has recently been redone inside and is fresh & clean and perfect for a great vacati …see more

from $129 / night

$900 - $1651 / week

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from $129 / night

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

$1700 - $2500 / week

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from $243 / night

19

Home rental in Oak Bluffs

Martha's Vineyard / Oak Bluffs

7 12 Min stay varies

  • 7 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
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 everything you need to make family dinners. Th …see more

from $429 / night

$3000 - $4000 / 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 $443 / night

$3101 - $7000 / week

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from $443 / night

20

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
Situated on quiet side street with a 15 minute walk or a 5 minute drive to town and beach, this light filled cape offers visiting families a well equipped vacation reprieve featuring comfortable living areas with mini split A/C and a modern spacious kitchen The first le …see more

from $308 / night

$2150 - $2590 / week

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from $308 / night

14

Vacation farmhouse in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
JUNE & JULY RATES REDUCED!! You will be within walking distance from downtown shopping, movie theatre, restaurants, bike path, harbor, beaches, and two-tenths of a mile from the brand-new modern library. Relaxed and warm, this brand-new home is expertly de …see more

from $575 / night

$3800 - $5200 / week

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from $575 / night

19

Vacation cottage in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This magnificent 1920’s East Chop cottage has been extensively redesigned, refurbished and expanded to allow friends and families to enjoy luxury accommodations along with rare double views of both Nantucket Sound and neighboring Crystal Lake. Complemented with a huge w …see more

from $750 / night

$2950 - $5975 / week

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from $750 / night

20

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Leave your worries and your car behind, this picture perfect Vineyard beach house is steps from downtown Oak Bluffs, the sandy beach and a few short blocks from the ferry. Recently renovated and restored, four-bedrooms and one and a half baths, offering the perfect jux …see more

from $429 / night

$3000 - $6500 / week

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from $429 / night

1