50 Best Oak Bluffs Vacation rentals on Holiday Lettings - Cottages

Close

Oak Bluffs

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

1,278 Vacation rentals

5

Vacation home rental

Martha's Vineyard / Oak Bluffs

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
Nestled in Historical Oak Bluffs is our one level cottage. It features a large (15x37) deck. Location. location. 1.5 miles from either ferry. Oak Bluffs or Vineyard Haven. . Distance to shopping , either town or going to the beach less then 2 miles. Public transportatio …see more

from $300 / night

$2,500 - $2,600 / week

Book View

Responds fast!
avg. 3 hours 29 minutes

from $300 / night

(1) Excellent 

19

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask about children
  • Air conditioning
Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs Center and beach area. Fully furnished screen porch. This home has been tastefully furnished throughout and will sleep families of 9 comfortably. \n Amenities and Features include...\n \nStyli …see more

from $575 / night

$4,025 - $4,225 / week

Inquire View

from $575 / 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

Inquire View

from $386 / 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

Inquire View

from $450 / night

21

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 is situated in an idyllic private wooded setting on Sengekontacket Pond, one of the largest salt-water ponds on Martha's Vineyard. Comfortably furnished, it has a newlyr renovated kitchen and a new dining area overlooking Major's Cove. There is also a …see more

from $243 / night

$1,700 - $4,800 / week

Inquire View

from $243 / 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

Inquire View

from $500 / 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) …see more

from $429 / night

$3,000 - $6,100 / week

Inquire View

from $429 / night

25

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
Gracious home features an open, airy floor plan. The large living area with all glass walls opens to a large private deck. Patio furnishings and dining table provide additional space for relaxing and barbecues. Spacious modern kitchen is equipped with all modern amen …see more

from $443 / night

$3,100 - $3,500 / week

Inquire View

from $443 / night

27

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • 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 $170 / night

$1,190 / week

Book View

Responds fast!
avg. 48 minutes

from $170 / night

12

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
This cozy, quaint waterfront property offers beautiful sunsets and great harbor views. Swimming, boating, kayaking, are just steps from this warm and charming quintessential Vineyard cottage. \n Amenities and Features include...\n \nWaterfront, Waterview Additional ame …see more

from $429 / night

$3,000 - $4,400 / week

Inquire View

from $429 / 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

Inquire View

from $189 / 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

Book View

from $400 / night

9

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
This whimsical summer home located in Water View Farms, provides a peaceful retreat overlooking wild flower meadows. Launch canoes or kayaks from the private association beach on Sengekontacket Pond, just a short walk from the house. Great waterfront play area for young …see more

from $308 / night

$2,150 - $2,350 / week

Inquire View

from $308 / night

36

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

7 12 7 nights min

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
New for 2018: All new Kitchen being completed at this time, not shown in current photos. 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. T …see more

from $2,143 / night

$15,000 - $17,650 / week

Inquire View

from $2,143 / 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 $286 / night

$2,000 - $3,450 / week

Inquire View

from $286 / 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

Inquire View

from $529 / 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

Inquire View

from $429 / 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 $500 / night

$3,500 - $4,400 / week

Inquire View

from $500 / 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 $500 / night

$3,500 - $4,500 / week

Inquire View

from $500 / 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 kitch …see more

from $529 / night

$3,700 - $4,700 / week

Inquire View

from $529 / 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

$3,000 - $6,500 / week

Inquire View

from $429 / 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 $86 / night

$602 / week

Book View

Responds fast!
avg. 26 minutes

from $86 / 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

Inquire View

from $1,143 / 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 …see more

from $354 / night

$2,475 - $4,825 / week

Inquire View

from $354 / 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
Extended families are sure to enjoy this Tri-level home featuring open floor plan on the main level, large main living room and two den TV areas one on the first level one and an additional TV area on the 2nd level. Kitchen has stainless appliance and granite counte …see more

from $286 / night

$2,000 - $3,500 / week

Inquire View

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

$2,500 - $5,000 / week

Inquire View

from $357 / 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 $429 / night

$3,000 - $4,000 / week

Inquire View

from $429 / 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

Inquire View

from $422 / 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 …see more

from $558 / night

$3,900 - $4,800 / week

Inquire View

from $558 / night

31

Vacation home with swimming pool in Oak Bluffs

Martha's Vineyard / Oak Bluffs

4 7 10 nights min

  • 4 bedrooms
  • Sleeps 7
  • 10 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Architect designed, luxury waterfront retreat. This unique home sits overlooking 500 feet of private lagoon beach and maintains sweeping waterviews up the lagoon. The pool and patio areas feature outdoor dining, sectional sofa seating, lounge area, and a hot tub all …see more

from $2,143 / night

$15,000 / week

Inquire View

from $2,143 / 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 $404 / night

$2,825 - $3,300 / week

Inquire View

from $404 / 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

Inquire View

from $222 / night

20

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
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 …see more

from $286 / night

$2,000 - $2,495 / week

Inquire View

from $286 / 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

Inquire View

from $352 / night

27

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
This grand Victorian jewel on Ocean Park has been completely renovated and transformed into a beautiful vacation home. Enjoy water and park views from inside this elegant home, the expansive wraparound porch and the second floor balcony. This beautifully restored Vic …see more

from $1,143 / night

$8,000 - $16,000 / week

Inquire View

from $1,143 / 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 $414 / night

$2,900 - $4,950 / week

Inquire View

from $414 / 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

Inquire View

from $429 / 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 spaci …see more

from $193 / night

$1,350 - $2,050 / week

Inquire View

from $193 / 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

Inquire View

from $343 / 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

Inquire View

from $297 / night