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

Holiday Homes in Oak Bluffs

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oak Bluffs holiday 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 NZ$1,316
includes taxes & fees
30 Aug - 31 Aug
< 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 NZ$2,283
includes taxes & fees
7 Sept - 8 Sept
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 NZ$1,178
includes taxes & fees
31 Aug - 1 Sept
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 NZ$1,365
includes taxes & fees
27 Sept - 28 Sept
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 NZ$1,375
includes taxes & fees
11 Sept - 12 Sept
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)
"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 NZ$3,605
includes taxes & fees
8 Sept - 9 Sept
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, (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 NZ$6,179
includes taxes & fees
13 Sept - 14 Sept
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 NZ$1,574
includes taxes & fees
31 Aug - 1 Sept
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 NZ$1,259
includes taxes & fees
8 Sept - 9 Sept
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
9.6 out of 10, Exceptional, (9 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is NZ$2,359
includes taxes & fees
7 Sept - 8 Sept
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 NZ$1,734
includes taxes & fees
2 Sept - 3 Sept
Walk to Town/Golf Club - Renovated Edgartown Home

12. 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 traveller
The price is NZ$2,094
includes taxes & fees
31 Aug - 1 Sept
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!

13. 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 NZ$2,034
includes taxes & fees
6 Sept - 7 Sept
The Seashell Cove - Martha's Vineyard

14. 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 NZ$1,271
includes taxes & fees
12 Sept - 13 Sept
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

15. 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 NZ$2,112
includes taxes & fees
8 Sept - 9 Sept
Recently renovated 3 bedroom

16. 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 NZ$1,242
includes taxes & fees
21 Sept - 22 Sept
Stunning 4-bedroom Private Fresh Water Beach Front

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, (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 NZ$2,148
includes taxes & fees
25 Sept - 26 Sept
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

18. 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)
"We had a great stay. Host was very friendly and the house was clean and perfect location for our trip. Very quiet area and beautiful lake view."
United States
Devin R.
The price is NZ$1,549
includes taxes & fees
7 Sept - 8 Sept
Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!

19. Haven in Hatchville - newly renovated home

Haven in Hatchville - newly renovated home
East Falmouth
The price is NZ$1,679
includes taxes & fees
8 Sept - 9 Sept
Haven in Hatchville - newly renovated home

20. 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 NZ$1,976
includes taxes & fees
20 Sept - 21 Sept
Adorable beach house! 3 min walk to 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Oak Bluffs Hotel Reviews

Find out more about Oak Bluffs

Oak Bluffs Holiday Homes information

Number of reviews
300
Accommodation
1334 Holiday Homes
Lowest Price
NZ$1,178
Highest Price
NZ$6,179