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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Oak Bluffs vacation 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 ￥56,684
￥132,787 total
includes taxes & fees
Oct 8 - Oct 9
Oak Bluffs 4BR • 5 Min Drive to Downtown
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

2. 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 ￥62,824
￥215,814 total
includes taxes & fees
Oct 6 - Oct 7
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A circular stone patio with Adirondack chairs and a small table in a forested area.

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 ￥49,881
￥112,844 total
includes taxes & fees
Oct 6 - Oct 7
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A spacious living room with a wooden staircase, a fireplace, and a leather sofa.

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 ￥68,980
￥148,284 total
includes taxes & fees
Oct 9 - Oct 10
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
A backyard with a seating area, a white fence, and a variety of plants.

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

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is ￥70,748
￥180,585 total
includes taxes & fees
Oct 30 - Oct 31
Delightful 3-bedroom house with AC in Oak Bluffs
A spacious living area with a high ceiling, a dining table, and a kitchen area.

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is ￥78,136
￥170,148 total
includes taxes & fees
Oct 6 - Oct 7
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A two-story house with a stone facade, a covered patio, and a well-maintained garden.

7. 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 ￥394,625
￥598,072 total
includes taxes & fees
Oct 12 - Oct 13
Beautiful Estate with salt water pool & pond with kayaks
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 ￥61,404
￥147,402 total
includes taxes & fees
Oct 6 - Oct 7
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 ￥213,098
￥352,461 total
includes taxes & fees
Oct 6 - Oct 7
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

10. 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, (12 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is ￥83,661
￥263,067 total
includes taxes & fees
Oct 12 - Oct 13
New 4 BR house near center and beaches with bikes
A deck with a fire pit, outdoor seating, and a blue umbrella.

11. Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.8 out of 10, Excellent, (8 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
The price is ￥37,109
￥128,460 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Cottage walk to Menauhant Beach
A boat docked at a concrete pier with a sandy shore in the background.

12. 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, (44 reviews)
"Great stay!"
United States
Kian S.
The price is ￥27,624
￥72,446 total
includes taxes & fees
Oct 6 - Oct 7
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

13. 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, (224 reviews)
"Great location "
United States
Stephanie B.
The price is ￥28,413
￥82,200 total
includes taxes & fees
Nov 1 - Nov 2
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.

14. 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 ￥118,388
￥188,838 total
includes taxes & fees
Oct 18 - Oct 19
The Seashell Cove - Martha's Vineyard
A beach with clear water and a sandy shore.

15. 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, (53 reviews)
"A wonderful home in a fabulous setting. The home has spacious & well laid out with a variety of beautiful outdoor spaces. Comfortable, with sufficient spaces inside and out; everyone had space to enjoy the property. We stayed for a week and never tired of the outdoor views. Convenient to great shopping and excellent beaches."
United States
Eric S.
The price is ￥70,401
￥162,775 total
includes taxes & fees
Oct 30 - Oct 31
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
A bedroom with a bed, two windows with curtains, a door, a bedside table with a lamp, and a picture on the wall.

16. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is ￥33,464
￥121,424 total
includes taxes & fees
Oct 6 - Oct 7
West Falmouth Family Retreat Near Chapoquoit Beach
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, (43 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 ￥44,750
￥109,208 total
includes taxes & fees
Oct 11 - Oct 12
Stunning 4-bedroom Private Fresh Water Beach Front
A modern kitchen with white cabinetry, a central island, skylights, and a view of the outdoors.

18. Recently renovated 3 bedroom

Recently renovated 3 bedroom
Falmouth
10.0 out of 10, Exceptional, (4 reviews)
"The home worked out well for our needs. They have a very nice fully fenced in yard which was very beneficial."
United States
Rosemary P.
The price is ￥66,791
￥189,245 total
includes taxes & fees
Oct 6 - Oct 7
Recently renovated 3 bedroom
A living room with a sectional sofa, a coffee table, a TV, and a fireplace.

19. 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 ￥38,610
￥152,172 total
includes taxes & fees
Oct 6 - Oct 7
Nice home near Mashpee Commons and all Falmouth has to offer
A covered outdoor seating area with a view of the ocean, a ceiling fan, and a flat-screen TV on the wall.

20. 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, (100 reviews)
"We had an amazing stay and hope to be back again! The house was clean, comfortable, and just as pictured."
United States
Melina G.
The price is ￥140,346
￥265,046 total
includes taxes & fees
Oct 18 - Oct 19
Coastal chic meets French Provençal in this newly renovated oceanfront home.
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

Summercamp

Summercamp

10/10 Excellent
"Staff was great, rooms and public spaces were clean, parking was a bit tight."
Maureen 3-night trip
Posted 12 hours ago
Summercamp

Find out more about Oak Bluffs

Oak Bluffs Vacation Homes information

Number of reviews
573
Accommodation
1327 Vacation Homes
Lowest Price
￥72,446
Highest Price
￥598,072