50 Best Oak Bluffs Vacation rentals on Holiday Lettings - Cottages

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139 Vacation rentals

19

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
Located just on the outskirts of Oak Bluffs and overlooking the lagoon this sweet summer home offers walking access to the lagoon for morning swims and is a great area for kayak enthusiasts. The sun filled interior features open living kitchen and dining area with a wal …see more

from $429 / night

$3000 - $4000 / week

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from $429 / night

(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

$1701 - $2000 / week

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from $243 / 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

$1450 - $2000 / week

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from $250 / 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 waterfron …see more

from $529 / night

$3701 - $5500 / week

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from $529 / 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 room …see more

from $422 / night

$2950 - $4850 / week

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from $422 / 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 $365 / night

$2550 - $6300 / week

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from $365 / night

6

Vacation private room in Oak Bluffs

Martha's Vineyard / Oak Bluffs

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
Welcome Martha's Vineyard, all people, local/foreign/happy/LGBT/Spiritual-not! Our home is located across from Norton's Farm and public transportation. Car and motorbike are best to access everything from this location. Our location is quiet, cozy and convenient all …see more

from $130 / night

$865 - $1015 / week

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from $130 / night

23

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
Spacious sun filled contemporary home located on a quiet private street,a 10 minute walk to town center, Inkwell Beach and harborfront, The first level features a spacious kitchen with stainless steel appliances, prep counter with range top. and breakfast nook, there is …see more

from $593 / night

$4150 - $5050 / week

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from $593 / 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
Walk to the beach! Walk to restaurants and shopping! Walk the kids to the arcade, Flying Horses Carousel, and lots of ice cream! Stay at a beautiful and bright home in the Historic Copeland District in Oak Bluffs. This 1928 home is mere minutes from dining and shopping …see more

from $429 / night

$3000 - $5500 / week

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from $429 / night

30

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 Meadow View Farms home, bordered by expansive landscaped yard, peaceful private setting. Association tennis courts just a short distance from the house and Farm Neck Golf and Tennis is just a half mile from the house. Miles of connecting bike paths begin at th …see more

from $458 / night

$3200 - $6000 / week

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from $458 / 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 - $6600 / week

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from $429 / night

(1) Very Good 

23

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

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

37

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Ask about children
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 Vineyard Sound from all areas of the home. Private path lea …see more

from $1629 / night

$11400 - $13400 / week

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from $1629 / night

(1)  

44

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
*Fall/Winter/Spring multi-week discount available *Only 1 prime summer week left! Check my calendar and book ASAP if you plan to visit in the peak season. *Perfect location so No Car Needed. Easy walk to town, beach & parks. The Pennacook house in Oak Bluffs on the c …see more

from $800 / night

$2800 - $6500 / week

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from $800 / 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 comfort …see more

from $465 / night

$3250 - $4250 / week

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from $465 / 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

$4500 - $5200 / week

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from $575 / 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

(3) 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 - $3300 / week

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from $200 / night

14

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children
  • Air conditioning
Come and enjoy the newly renovated two bedroom home in Oak Bluffs. The first floor which is done in bright coastal colors has a nice eat in kitchen with a couple steps up to the living room with a large flat screen TV. The first floor also have a half bath. The secon …see more

from $286 / night

$2000 - $2300 / week

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from $286 / night

19

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Air conditioning
Newly renovated and painted campground Victorian home with gingerbread accents. This charming Victorian is ideally located close to town, shops, restaurants and beaches. Enjoy peeks of the harbor while watching the sunset from the new roof top deck. Additional amenitie …see more

from $357 / night

$2500 - $4400 / week

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from $357 / 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 beautif …see more

from $429 / night

$3000 - $5300 / week

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from $429 / night

21

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 Oak Bluffs home close to town and beach. This home has an open floor plan which is nice for relaxing with family and friends. Also enjoy the screened porch off the living area. Additional amenities include: coffee maker, outdoor shower, cd player, wine glas …see more

from $400 / night

$2800 - $4000 / week

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from $400 / night

21

Home rental in Oak Bluffs

Martha's Vineyard / Oak Bluffs

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Beautiful luxury home overlooking Farm Neck Golf Course and Sengekontacket Pond. Large family living spaces include a great room with soaring ceilings opening to the patio as well as a large TV/family room. Expansive gourmet kitchen with dining area is great for family …see more

from $1214 / night

$8500 - $15000 / week

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from $1214 / night

23

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
  • Air conditioning
Views, Views and more Views! Lovely water views of Sengekontacket Pond over the rolling "forever" conservation land. Large contemporary home has been recently updated to 4 bedrooms and 3 full baths. Large open living space with deck overlooking the view and sun room. Ac …see more

from $571 / night

$4000 - $6000 / week

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from $571 / night

20

Vacation home rental

Martha's Vineyard / Oak Bluffs

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Beautiful waterfront home with central A/C, features open floor plan and sunny living spaces. The great room has two distinct seating areas and is equipped with a flat screen TV. There is a formal dining room set between the living area and kitchen and opens to the outd …see more

from $686 / night

$4800 - $7300 / week

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from $686 / night

15

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • 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

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

15

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
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, dining, movies, shops and galleries. Amenities and …see more

from $786 / night

$5500 - $7200 / week

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from $786 / night

18

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
This adorable Gingerbread cottage is located only a block to town and a couple of blocks to the beach. You can enjoy morning coffee on the covered wrap around porch that leads into a cute sitting room with a TV and another small sitting area off of the front room. There …see more

from $214 / night

$1500 - $3200 / week

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from $214 / night

20

Home rental in Oak Bluffs

Martha's Vineyard / Oak Bluffs

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Air conditioning
Gracious 5 bedroom in-town victorian offers easy access to shopping, ferry, park with basketball and tennis and beach. This home has been lovingly maintained and restored to it's prior elegance. Enjoy cocktails on the beautiful three season porch. Additional amenities …see more

from $586 / night

$4100 - $4400 / week

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from $586 / night

18

Vacation home rental

Martha's Vineyard / Oak Bluffs

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Beautiful four bedroom house in the prestigious Farm Neck area overlooking a lovely lawn to a large tidal pond. This home offers an open floor plan so the whole family can be together. The kitchen and living areas open up to a wonderful deck so you can enjoy the views …see more

from $643 / night

$4500 - $6500 / week

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from $643 / 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 $543 / night

$3800 - $7500 / week

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from $543 / night

26

Oak Bluffs Vacation cottage rental

Martha's Vineyard / Oak Bluffs

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
This fabulous 125 year-old Victorian cottage was lovingly updated and completely restored in 2012. Sitting on a large private lot, just steps from Inkwell beach, Solera offers the perfect balance of comfort, ambiance and vintage charm. The large, airy gourmet kitchen w …see more

from $500 / night

$3200 - $7500 / week

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from $500 / 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

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 $329 / night

$2300 - $3350 / week

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from $329 / 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 $314 / night

$2200 - $3900 / week

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from $314 / night

(1) Very Good 

22

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

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

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 Oa …see more

from $247 / night

$1725 - $2450 / week

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from $247 / night

1