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 ¥50,289
¥122,792 total
includes taxes & fees
Sep 24 - Sep 25
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

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, (8 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is ¥61,447
¥211,083 total
includes taxes & fees
Oct 1 - Oct 2
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

3. 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 ¥48,787
¥110,370 total
includes taxes & fees
Sep 13 - Sep 14
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

4. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is ¥61,602
¥127,960 total
includes taxes & fees
Sep 27 - Sep 28
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 ¥48,633
¥131,066 total
includes taxes & fees
Sep 17 - Sep 18
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

6. 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 ¥385,975
¥584,618 total
includes taxes & fees
Oct 12 - Oct 13
Beautiful Estate with salt water pool & pond with kayaks

7. 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 ¥206,982
¥342,345 total
includes taxes & fees
Sep 24 - Sep 25
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

8. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is ¥60,058
¥144,171 total
includes taxes & fees
Sep 13 - Sep 14
Walk to Beach! Oak Bluffs Home & Studio

9. 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 ¥29,563
¥117,232 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Cottage walk to Menauhant Beach

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, (11 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is ¥81,260
¥224,007 total
includes taxes & fees
Sep 23 - Sep 24
New 4 BR house near center and beaches with bikes

11. 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, (43 reviews)
"Great stay!"
United States
Kian S.
The price is ¥27,018
¥70,327 total
includes taxes & fees
Oct 1 - Oct 2
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

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, (221 reviews)
"Great location "
United States
Stephanie B.
The price is ¥42,457
¥100,012 total
includes taxes & fees
Oct 5 - Oct 6
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

13. Beautiful Home in Falmouth Village

Beautiful Home in Falmouth Village
Falmouth
10.0 out of 10, Exceptional, (16 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.
Beautiful Home in Falmouth Village

14. Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
East Falmouth
10.0 out of 10, Exceptional, (48 reviews)
"A perfect location and awesome for a family vacation"
United States
joyce b.
The price is ¥23,159
¥151,079 total
includes taxes & fees
Oct 12 - Oct 13
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

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 ¥46,549
¥106,463 total
includes taxes & fees
Sep 21 - Sep 22
Stunning 4-bedroom Private Fresh Water Beach Front

16. 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 ¥1,373,934
¥1,875,507 total
includes taxes & fees
Sep 16 - Sep 17
Coastal chic meets French Provençal in this newly renovated oceanfront home.

17. 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 ¥62,023
¥177,081 total
includes taxes & fees
Sep 20 - Sep 21
Recently renovated 3 bedroom

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, (52 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 ¥81,055
¥170,516 total
includes taxes & fees
Oct 2 - Oct 3
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

19. 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 ¥57,645
¥149,522 total
includes taxes & fees
Sep 22 - Sep 23
Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi

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

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (13 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
The price is ¥54,191
¥125,635 total
includes taxes & fees
Sep 13 - Sep 14
Spring Escape in Hatchville – Sleeps 6 + Dogs!
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
560
Accommodation
1327 Vacation Homes
Lowest Price
¥100,012
Highest Price
¥1,875,507