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

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Our top choices for Oak Bluffs vacation homes

1. < 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 ¥52,136
¥127,302 total
includes taxes & fees
Aug 30 - Aug 31
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

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

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.2 out of 10, (10 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 ¥50,228
¥113,630 total
includes taxes & fees
Aug 25 - Aug 26
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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, (8 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is ¥69,143
¥222,112 total
includes taxes & fees
Sep 7 - Sep 8
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

4. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is ¥79,316
¥151,980 total
includes taxes & fees
Sep 8 - Sep 9
Charming Vacation Home in Oak Bluffs.

5. 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 ¥50,069
¥133,516 total
includes taxes & fees
Sep 11 - Sep 12
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

6. 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)
"TLDR: House is nice,"
United States
Rachel
The price is ¥214,583
¥349,058 total
includes taxes & fees
Sep 8 - Sep 9
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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, (2 reviews)
"The house and hosts are extraordinary! The property is gorgeous, from the landscaping to the architecture. We loved the saltwater pool, hot tub, and private pond access. The rooms were spacious, the beds were comfortable, the house was spotless, and the hosts provided every toiletry and towel we could possibly need. They were incredibly kind and excellent communicators. They even let us drop off our golf bags early in the morning so we could explore the island before our tee time at the nearby...
United States
Michael T.
The price is ¥389,428
¥595,138 total
includes taxes & fees
Sep 22 - Sep 23
Beautiful Estate with salt water pool & pond with kayaks

8. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is ¥61,832
¥152,337 total
includes taxes & fees
Aug 31 - Sep 1
Walk to Beach! Oak Bluffs Home & Studio

9. A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!

A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!
Tisbury
10.0 out of 10, Exceptional, (31 reviews)
"Host was very informative before the arrival, house was spotless and everything was easy to find "
United States
Anonymous traveler
A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!

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

New 4 BR house near center and beaches with bikes
Katama
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is ¥84,244
¥229,570 total
includes taxes & fees
Sep 7 - Sep 8
New 4 BR house near center and beaches with bikes

11. Walk to Town/Golf Club - Renovated Edgartown Home

Walk to Town/Golf Club - Renovated Edgartown Home
Edgartown
10.0 out of 10, Exceptional, (47 reviews)
"Great house in a great location—just a short, easy walk to downtown Edgartown"
United States
Steven M.
The price is ¥83,687
¥167,338 total
includes taxes & fees
Sep 2 - Sep 3
Walk to Town/Golf Club - Renovated Edgartown Home

12. Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Falmouth
10.0 out of 10, Exceptional, (18 reviews)
"This is a beautiful and unique home with plenty of space and activities for the family. The photos were accurate and there was so much space for everyone to relax. We enjoyed our stay so much. "
United States
Lisa F.
The price is ¥52,930
¥120,067 total
includes taxes & fees
Sep 1 - Sep 2
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

13. serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is ¥50,069
¥124,817 total
includes taxes & fees
Sep 22 - Sep 23
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

14. Walk to downtown Edgartown in quiet neighborhood - Perfect Location!

Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
Edgartown
10.0 out of 10, Exceptional, (5 reviews)
"One of the most well equipped vacation rentals I’ve stayed in. A simple, but well curated place. Thank you to our hosts!"
United States
Anonymous traveler
The price is ¥119,213
¥202,582 total
includes taxes & fees
Aug 31 - Sep 1
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!

15. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (29 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is ¥119,213
¥192,106 total
includes taxes & fees
Sep 6 - Sep 7
The Seashell Cove - Martha's Vineyard

16. Elisa's Cottage - Your Family Vacation Destination

Elisa's Cottage - Your Family Vacation Destination
Woods Hole
10.0 out of 10, Exceptional, (8 reviews)
"We enjoyed the proximity to Woods Hole and Falmouth and the added snack touches. "
United States
Stefanie G.
The price is ¥85,901
¥174,536 total
includes taxes & fees
Aug 27 - Aug 28
Elisa's Cottage - Your Family Vacation Destination

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, (42 reviews)
"We rented this cape property for a long cousin girls weekend. The host was responsive. The house was everything and more. Lisa had the property well stocked with paper goods, linens, and thoughtful extras. We went kayaking on the lake, played cards, did some day excursions. Thank you so much for sharing your home with us. "
United States
Erica M.
The price is ¥53,248
¥121,705 total
includes taxes & fees
Sep 21 - Sep 22
Stunning 4-bedroom Private Fresh Water Beach Front

18. 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, (51 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 ¥119,213
¥228,127 total
includes taxes & fees
Aug 29 - Aug 30
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

19. Adorable beach house! 3 min walk to beach!

Adorable beach house! 3 min walk to beach!
Popponesset
9.8 out of 10, Exceptional, (30 reviews)
"We had a great stay! The place was clean, well decorated, and close to the beach! The property managers were also very nice and easy to reach out to!"
United States
Allison W.
The price is ¥92,986
¥172,459 total
includes taxes & fees
Sep 22 - Sep 23
Adorable beach house! 3 min walk to beach!

20. Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!

Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!
East Falmouth
9.8 out of 10, Exceptional, (76 reviews)
"This property is 100% portrayed as in the photos. The view is exactly as beautiful as in the photos. My family and I enjoyed are stay in this gorgeous home. "
United States
Erin S.
The price is ¥85,038
¥163,181 total
includes taxes & fees
Sep 7 - Sep 8
Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!
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
Accommodation
1396 Vacation Homes
Lowest Price
¥137,322
Highest Price
¥137,322