50 Best Oak Bluffs Vacation rentals on Holiday Lettings - Cottages

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152 Vacation rentals

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

25

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Stay in this peaceful, well-maintained home with a large wrap-around porch, a deck, and in close proximity to the ocean for your next unforgettable New England vacation. Come with a small group of friends, bring your own small family, or get away with another couple and …see more

from $218 / night

$1520 / week

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from $218 / 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 $743 / night

$5200 / week

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from $743 / night

30

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
Come and enjoy this beautiful waterfront home on East Chop! The first floor has a wonderful front seasonal porch with views of the Vineyard Sound. There is a large dining table and room to relax and take in the view. There is also a living room that leads into the kit …see more

from $1715 / night

$12000 / week

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from $1715 / night

21

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
Sitting on the "summer porch" (that is what they were called in the days of old) sipping your favorite beverage, strolling the short distant to the water, relaxing around the table, Well equipped kitchen, reading in the living room with your feet these are possible whe …see more

from $500 / night

$3500 - $5000 / week

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from $500 / 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

29

Home rental 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
Situated on Lagoon Pond enjoy the stunning views and sunsets from this contemporary home. Bring your boat and tie up to the 65 foot dock. (Low tide is 2FT) The home features four bedrooms and three and a half bathrooms spacious enough for the whole family to spread out. …see more

from $929 / night

$6501 - $10000 / week

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from $929 / night

6

Vacation private room in Oak Bluffs

Martha's Vineyard / Oak Bluffs

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 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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avg. 3 hours 41 minutes

from $130 / 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

(4) Very Good 

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

25

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
You'll love this Oak Bluffs vacation rental with plenty of entertainment and a beautiful gourmet kitchen! The surrounding area is quiet and residential, and the water is less than a mile to the northwest. To get to the heart of Oak Bluffs and its shops and restaurants, …see more

from $107 / night

$743 / week

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from $107 / 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

12

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
Air conditioning has been added for the 2017 season! Waterview Farm is a private association with wonderful meadow and water views. It is adjacent to Farm Neck Golf and Tennis Club, which is open the public. There is access to Sengekontacket Pond to launch canoes and k …see more

from $286 / night

$2000 - $3500 / week

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from $286 / 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 - $11000 / week

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from $571 / 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

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 $243 / night

$1700 - $2800 / 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

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

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 $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

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 $143 / night

$1000 - $1650 / week

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from $143 / 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 - $2400 / week

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from $157 / night

17

Vacation home 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
Charming six bedroom home located within walking distance to town. The first floor has a nice living room/dining area with doors that open to the front porch. There are two bedroom and one full bath on the first floor too. The second floor has four additional bedroom …see more

from $429 / night

$3000 - $3900 / 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 - $3251 / week

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from $143 / 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 $117 / night

$819 / week

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from $117 / night

14

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
This charming home sits atop the Lagoon bluffs w/stairs down to a narrow private beach It offers waterviews from many rooms (including a wonderful glassed in/screened porch). The living room sports bay windows to access the view, and there's a studio w/a private entranc …see more

from $457 / night

$3200 - $4900 / week

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from $457 / 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

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 $222 / night

$1550 - $2740 / week

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from $222 / 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

$3251 - $4250 / week

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from $465 / 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

19

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
Enjoy the charm of a Vineyard cottage with all the amenities of today. This 3 bedroom house has brand new furnishings for 2015. It is in a quiet neighborhood not far from Oak Bluffs center and its harbor. The house is also close to the bike path. The house has an open f …see more

from $243 / night

$1700 - $2800 / week

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from $243 / 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

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 me …see more

from $1379 / night

$9650 - $15150 / week

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from $1379 / 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 yard …see more

from $172 / night

$1200 - $4225 / week

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from $172 / night

(2) Very Good 

22

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
A true Vineyard classic from 1890, this house retains its authentic charm yet has been thoughtfully renovated and serves the modern day vacationer well. The 8 bedrooms afford plenty of space to accomodate larger family groups for special reunions and vacations. The livi …see more

from $671 / night

$4700 - $9425 / week

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from $671 / night

15

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
This is a wonderful vacation house located about a 10 minute walk to town and little further to the town beach. The home was recently renovated and has a nice open floor plan on the main level which has an updated kitchen, family room and dining space. There is also a …see more

from $357 / night

$2500 - $4000 / week

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from $357 / night

11

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Home away from Home! Walk to Sailing Camp! Bright, sunny 3 bedroom Cape style vacation home in Lagoon Heights with great amenities. Fully furnished home with 2 baths, outdoor shower, large deck and private enclosed yard and a wonderful deck for the summer cookouts. …see more

from $300 / night

$2300 / week

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from $300 / night

40

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

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 - $6000 / week

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from $429 / 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 $465 / night

$3251 - $3475 / week

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from $465 / night