A row of colorful, historic houses with a central path.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Oak Bluffs holiday homes

A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

1. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
The price is HK$2,345
HK$5,843 total
includes taxes & fees
11 Nov - 12 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown
A circular stone patio with Adirondack chairs and a small table in a forested area.

2. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
The price is HK$2,063
HK$5,072 total
includes taxes & fees
2 Nov - 3 Nov
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A modern kitchen with a large island, a dining area with a table and chairs, and a view of a green garden through large windows.

3. Vineyard Luxury "Yurt"

Vineyard Luxury "Yurt"
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"The yurt was clean and nice and served all of our needs."
United States
David C.
The price is HK$2,314
HK$4,233 total
includes taxes & fees
30 Oct - 31 Oct
Vineyard Luxury "Yurt"
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

4. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (10 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is HK$3,122
HK$10,726 total
includes taxes & fees
28 Oct - 29 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A spacious living room with a wooden staircase, a fireplace, and a leather sofa.

5. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
Oak Bluffs
7.4 out of 10, Good, (3 reviews)
"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...
United States
Kate K.
The price is HK$3,427
HK$7,367 total
includes taxes & fees
2 Nov - 3 Nov
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
A modern kitchen with a central island, bar stools, stainless steel appliances, and a large window with a view of the outdoors.

6. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is HK$3,516
HK$9,019 total
includes taxes & fees
30 Oct - 31 Oct
Delightful 3-bedroom house with AC in Oak Bluffs
A spacious living area with a high ceiling, a dining table, and a kitchen area.

7. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (11 reviews)
"A clean accommodating space with an accommodating host - I recommended!"
United States
Collins E.
The price is HK$3,882
HK$8,454 total
includes taxes & fees
2 Nov - 3 Nov
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

8. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is HK$2,439
HK$6,579 total
includes taxes & fees
2 Nov - 3 Nov
Walk to Beach! Oak Bluffs Home & Studio
A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

9. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (12 reviews)
"This was an excellent stay at a beautiful property in Oak Bluffs! Rebecca was a great host who provided clear instructions and helped answer questions in a timely manner. Rooms were spacious, most tastefully decorated and we had everything that we needed. I definitely recommend staying here to have an unparalleled experience of the Vineyard."
United States
Priyanka D.
The price is HK$10,587
HK$17,511 total
includes taxes & fees
29 Oct - 30 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
A boat docked at a concrete pier with a sandy shore in the background.

10. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
10.0 out of 10, Exceptional, (45 reviews)
"Great place with kayaks and paddle boards, beach, close to Mashpee Commons. Host was great and place was clean and quaint."
United States
Michele M.
The price is HK$1,235
HK$3,424 total
includes taxes & fees
28 Oct - 29 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A modern kitchen with white cabinetry, a dining area with a wooden table and white chairs, and a large window providing natural light.

11. New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
9.8 out of 10, Exceptional, (13 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is HK$4,690
HK$13,753 total
includes taxes & fees
15 Nov - 16 Nov
New 4 BR house near center and beaches with bikes
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

12. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (225 reviews)
"Great location "
United States
Stephanie B.
The price is HK$1,412
HK$4,102 total
includes taxes & fees
1 Nov - 2 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A spacious living area with wooden beams, a dining table, and a sofa.

13. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (31 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is HK$5,649
HK$9,210 total
includes taxes & fees
28 Oct - 29 Oct
The Seashell Cove - Martha's Vineyard
A beach with clear water and a sandy shore.

14. New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
9.8 out of 10, Exceptional, (54 reviews)
"We had the best week at 67 Tide Run! The property is gorgeous. We enjoyed kayaking and fishing from the dock. It was plenty big enough for our family of 10. We are going to miss the views. It’s perfect! You cannot go wrong booking Jamie’s home."
United States
cindy w.
The price is HK$4,313
HK$9,191 total
includes taxes & fees
30 Oct - 31 Oct
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
A modern kitchen with white cabinetry, a black stove, and a stainless steel sink.

15. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is HK$1,917
HK$5,835 total
includes taxes & fees
28 Oct - 29 Oct
West Falmouth Family Retreat Near Chapoquoit Beach
A spacious kitchen with a large island, wooden flooring, and a dining area with chairs and a table.

16. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
Falmouth
10.0 out of 10, Exceptional, (19 reviews)
"Jessica was absolutely amazing and so was the house! We stayed here for our family vacation and it was perfect. 5 stars all around!"
United States
Kelsey B.
The price is HK$2,974
HK$7,290 total
includes taxes & fees
2 Nov - 3 Nov
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
A wooden deck overlooking a calm lake with trees and houses in the background.

17. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, Exceptional, (45 reviews)
"Great trip and time on the lake. Highly recommend this property for families looking for ease and convenience."
United States
Kathryn C.
The price is HK$2,153
HK$5,354 total
includes taxes & fees
2 Nov - 3 Nov
Stunning 4-bedroom Private Fresh Water Beach Front
A living room with a sectional sofa, a coffee table, a TV, and a fireplace.

18. Nice home near Mashpee Commons and all Falmouth has to offer

Nice home near Mashpee Commons and all Falmouth has to offer
Falmouth
6.0 out of 10, (3 reviews)
"Quiet location"
United States
andrea m.
The price is HK$1,919
HK$7,536 total
includes taxes & fees
28 Oct - 29 Oct
Nice home near Mashpee Commons and all Falmouth has to offer
A coastal road with a rocky breakwater and a stack of stones.

19. Beautiful Home in Falmouth Village

Beautiful Home in Falmouth Village
Falmouth
10.0 out of 10, Exceptional, (17 reviews)
"We had a family reunion and 75 Locust Street was the central hub of the four night stay. The house is beautiful, clean and we had family from all over stay there. We'd go back in a heartbeat. Easy access to downtown and the hosts were communicative and informative."
United States
Melissa L.
The price is HK$3,494
HK$9,142 total
includes taxes & fees
28 Oct - 29 Oct
Beautiful Home in Falmouth Village
A room with a white dresser, a lamp, a window with blinds, and a view of a deck and houses outside.

20. Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
Backyard Retreat / 5 Min > Beach & Main St
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oak Bluffs Hotel Reviews

Sea Crest Beach Resort

Sea Crest Beach Resort

10/10 Excellent
"The hotel is amazing, very nice beach view and the staff is so friendly"
Alessandra 2-night trip
Posted 16 hours ago
Sea Crest Beach Resort

Find out more about Oak Bluffs

Oak Bluffs Vacation Homes information

Number of reviews
222
Accommodation
1314 Vacation Homes
Lowest Price
HK$3,424
Highest Price
HK$17,511

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