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, 3, (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 AED 1,605
AED 3,450 total
includes taxes & fees
15 Sep - 16 Sep
< 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
6.6 out of 10, 11, (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 AED 1,230
AED 2,716 total
includes taxes & fees
11 Oct - 12 Oct
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, 9, (9 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is AED 1,462
AED 4,796 total
includes taxes & fees
1 Oct - 2 Oct
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 AED 1,319
AED 2,831 total
includes taxes & fees
27 Sep - 28 Sep
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, 9, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is AED 1,157
AED 3,118 total
includes taxes & fees
17 Sep - 18 Sep
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, 3, (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 AED 9,183
AED 14,056 total
includes taxes & fees
12 Oct - 13 Oct
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, 12, (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 AED 4,959
AED 7,865 total
includes taxes & fees
19 Sep - 20 Sep
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 AED 1,429
AED 3,430 total
includes taxes & fees
25 Sep - 26 Sep
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, 8, (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 AED 724
AED 2,836 total
includes taxes & fees
27 Sep - 28 Sep
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, 11, (11 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is AED 1,947
AED 5,124 total
includes taxes & fees
16 Sep - 17 Sep
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, 43, (43 reviews)
"Great stay!"
United States
Kian S.
The price is AED 643
AED 1,623 total
includes taxes & fees
1 Oct - 2 Oct
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, 221, (221 reviews)
"Great location "
United States
Stephanie B.
The price is AED 845
AED 2,161 total
includes taxes & fees
14 Oct - 15 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

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 AED 1,036
AED 3,800 total
includes taxes & fees
20 Sep - 21 Sep
Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

14. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, 31, (31 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is AED 2,938
AED 4,685 total
includes taxes & fees
14 Oct - 15 Oct
The Seashell Cove - Martha's Vineyard

15. 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 AED 1,364
AED 3,548 total
includes taxes & fees
27 Sep - 28 Sep
Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi

16. 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, 49, (49 reviews)
"A perfect location and awesome for a family vacation"
United States
joyce b.
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

17. Water Views, Walk to Fairmount Heights Beach

Water Views, Walk to Fairmount Heights Beach
Falmouth Heights
10.0 out of 10, 2, (2 reviews)
The price is AED 1,639
AED 3,847 total
includes taxes & fees
20 Sep - 21 Sep
Water Views, Walk to Fairmount Heights Beach

18. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, 42, (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 AED 1,107
AED 2,533 total
includes taxes & fees
21 Sep - 22 Sep
Stunning 4-bedroom Private Fresh Water Beach Front

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

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, 13, (13 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
Spring Escape in Hatchville – Sleeps 6 + Dogs!

20. 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, 53, (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 AED 1,928
AED 4,057 total
includes taxes & fees
2 Oct - 3 Oct
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
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