Photo by William Keller

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Our top choices for Oak Bluffs vacation homes

1. 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 ¥36,926
¥73,459 total
includes taxes & fees
Nov 8 - Nov 9
Vineyard Luxury "Yurt"

2. 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 ¥42,647
¥112,112 total
includes taxes & fees
Nov 20 - Nov 21
Oak Bluffs 4BR • 5 Min Drive to Downtown

3. 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 ¥41,680
¥99,940 total
includes taxes & fees
Nov 8 - Nov 9
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

4. < 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 ¥68,823
¥144,017 total
includes taxes & fees
Nov 8 - Nov 9
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

5. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (3 reviews)
"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."
United States
Lamar A.
The price is ¥316,960
¥492,085 total
includes taxes & fees
Nov 30 - Dec 1
Beautiful Estate with salt water pool & pond with kayaks

6. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is ¥49,287
¥136,215 total
includes taxes & fees
Nov 8 - Nov 9
Walk to Beach! Oak Bluffs Home & Studio

7. 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 ¥94,771
¥264,118 total
includes taxes & fees
Nov 15 - Nov 16
New 4 BR house near center and beaches with bikes

8. 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 ¥24,805
¥66,962 total
includes taxes & fees
Nov 10 - Nov 11
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

9. 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, (227 reviews)
"Great location "
United States
Stephanie B.
The price is ¥28,348
¥82,373 total
includes taxes & fees
Nov 16 - Nov 17
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10. Coastal chic meets French Provençal in this newly renovated oceanfront home.

Coastal chic meets French Provençal in this newly renovated oceanfront home.
East Falmouth
10.0 out of 10, Exceptional, (101 reviews)
"Great views, beautiful setting . Scott was so attentive and easy to work with. We had a great time!"
United States
Ben L.
The price is ¥54,867
¥152,941 total
includes taxes & fees
Nov 19 - Nov 20
Coastal chic meets French Provençal in this newly renovated oceanfront home.

11. 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 ¥106,974
¥168,173 total
includes taxes & fees
Nov 8 - Nov 9
The Seashell Cove - Martha's Vineyard

12. Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi

Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi
East Falmouth
The price is ¥51,343
¥137,158 total
includes taxes & fees
Nov 8 - Nov 9
Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi

13. 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 ¥52,140
¥130,413 total
includes taxes & fees
Dec 1 - Dec 2
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

14. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is ¥41,728
¥162,178 total
includes taxes & fees
Nov 8 - Nov 9
West Falmouth Family Retreat Near Chapoquoit Beach

15. 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 ¥48,336
¥114,633 total
includes taxes & fees
Nov 8 - Nov 9
Stunning 4-bedroom Private Fresh Water Beach Front

16. 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.
Nice home near Mashpee Commons and all Falmouth has to offer

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is ¥24,501
¥89,817 total
includes taxes & fees
Nov 10 - Nov 11
Backyard Retreat / 5 Min > Beach & Main St

18. Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach
Sandwich
The price is ¥31,696
¥59,130 total
includes taxes & fees
Nov 8 - Nov 9
Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

19. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (40 reviews)
"Beautiful and relaxing location."
United States
Lauren F.
The price is ¥35,658
¥75,589 total
includes taxes & fees
Nov 30 - Dec 1
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

20. Pool Escape in East Falmouth

Pool Escape in East Falmouth
East Falmouth
8.0 out of 10, Very good, (2 reviews)
"Great location! Close to everything and wonderful neighborhood. The fenced in back yard with the pool is amazing. Hosts are great to work with. Very responsive to any questions or needs."
United States
Gloria C.
The price is ¥75,448
¥198,558 total
includes taxes & fees
Nov 8 - Nov 9
Pool Escape in East Falmouth
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.

Learn more about Oak Bluffs

The colorful gingerbread cottages of the Martha's Vineyard Campground will charm you with their whimsical Victorian details. Take the Flying Horses carousel for a spin, then stroll along Ocean Park's waterfront where locals gather for sunset picnics.

A historic two-story house with a balcony and a porch, surrounded by a well-maintained garden.
Photo by William Keller
Open Photo by William Keller

Top reviews in Oak Bluffs