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

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Our top choices for Oak Bluffs vacation homes

1. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
Oak Bluffs
8.8 out of 10, Excellent, (9 reviews)
"Loved our little cottage"
United States
Linda T.
The price is ¥62,517
¥140,370 total
includes taxes & fees
Sep 28 - Sep 29
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

2. < 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 ¥69,164
¥147,087 total
includes taxes & fees
Sep 26 - Sep 27
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

3. 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, (9 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is ¥62,991
¥216,388 total
includes taxes & fees
Oct 1 - Oct 2
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

4. 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 ¥56,835
¥133,140 total
includes taxes & fees
Sep 27 - Sep 28
Oak Bluffs 4BR • 5 Min Drive to Downtown

5. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.6 out of 10, (11 reviews)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
The price is ¥50,013
¥108,017 total
includes taxes & fees
Sep 29 - Sep 30
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

6. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is ¥61,567
¥148,502 total
includes taxes & fees
Sep 29 - Sep 30
Walk to Beach! Oak Bluffs Home & Studio

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is ¥78,344
¥165,650 total
includes taxes & fees
Oct 4 - Oct 5
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

8. 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 ¥213,665
¥353,398 total
includes taxes & fees
Oct 2 - Oct 3
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

9. 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 ¥395,675
¥578,626 total
includes taxes & fees
Oct 18 - Oct 19
Beautiful Estate with salt water pool & pond with kayaks

10. 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 ¥30,306
¥120,722 total
includes taxes & fees
Sep 30 - Oct 1
Cozy Cottage walk to Menauhant Beach

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, (11 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is ¥83,883
¥231,239 total
includes taxes & fees
Sep 27 - Sep 28
New 4 BR house near center and beaches with bikes

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 ¥27,697
¥72,095 total
includes taxes & fees
Sep 27 - Sep 28
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

13. Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow
Falmouth
The price is ¥44,634
¥163,742 total
includes taxes & fees
Sep 28 - Sep 29
Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

14. 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, (223 reviews)
"Great location "
United States
Stephanie B.
The price is ¥36,402
¥93,107 total
includes taxes & fees
Oct 18 - Oct 19
Located Steps Away To Main Street And .7 Miles From Surf Drive 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, (42 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 ¥47,718
¥114,209 total
includes taxes & fees
Sep 27 - Sep 28
Stunning 4-bedroom Private Fresh Water Beach Front

16. 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 ¥118,703
¥189,871 total
includes taxes & fees
Oct 18 - Oct 19
The Seashell Cove - Martha's Vineyard

17. 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 ¥83,092
¥181,142 total
includes taxes & fees
Oct 2 - Oct 3
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

18. Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (14 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
Spring Escape in Hatchville – Sleeps 6 + Dogs!

19. Recently renovated 3 bedroom

Recently renovated 3 bedroom
Falmouth
10.0 out of 10, Exceptional, (3 reviews)
"Stay was awesome! Perfect house for family gatherings "
United States
Diana P.
The price is ¥57,252
¥173,362 total
includes taxes & fees
Oct 4 - Oct 5
Recently renovated 3 bedroom

20. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is ¥33,553
¥121,747 total
includes taxes & fees
Oct 5 - Oct 6
West Falmouth Family Retreat Near Chapoquoit Beach
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

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Oak Bluffs Vacation Homes information

Number of reviews
442
Accommodation
1327 Vacation Homes
Lowest Price
¥93,107
Highest Price
¥578,626