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

Holiday Homes in Oak Bluffs

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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 €686
includes taxes & fees
7 Sept - 8 Sept
< 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 €1,222
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 €610
includes taxes & fees
13 Sept - 14 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 €714
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 €724
includes taxes & fees
17 Sept - 18 Sept
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 €3,251
includes taxes & fees
14 Sept - 15 Sept
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 €1,909
includes taxes & fees
8 Sept - 9 Sept
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 €823
includes taxes & fees
2 Sept - 3 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 €656
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.
New 4 BR house near center and beaches with bikes

11. 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 €669
includes taxes & fees
13 Sept - 14 Sept
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

12. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.6 out of 10, Exceptional, (30 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The Seashell Cove - Martha's Vineyard

13. 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 €1,067
includes taxes & fees
13 Sept - 14 Sept
Recently renovated 3 bedroom

14. 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 €668
includes taxes & fees
21 Sept - 22 Sept
Stunning 4-bedroom Private Fresh Water Beach Front

15. 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 €1,041
includes taxes & fees
29 Sept - 30 Sept
Adorable beach house! 3 min walk to beach!

16. 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 €1,103
includes taxes & fees
25 Sept - 26 Sept
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

17. 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.
Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!

18. Haven in Hatchville - newly renovated home

Haven in Hatchville - newly renovated home
East Falmouth
The price is €879
includes taxes & fees
8 Sept - 9 Sept
Haven in Hatchville - newly renovated home

19. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is €827
includes taxes & fees
1 Oct - 2 Oct
West Falmouth Family Retreat Near Chapoquoit Beach

20. Nice home near Mashpee Commons and all Falmouth has to offer

Nice home near Mashpee Commons and all Falmouth has to offer
Falmouth
6.0 out of 10, (3 reviews)
"Quiet location"
United States
andrea m.
Nice home near Mashpee Commons and all Falmouth has to offer
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 Holiday Homes information

Number of reviews
269
Accommodation
1334 Holiday Homes
Lowest Price
€610
Highest Price
€3,251