Oak Bluffs Holiday Rentals

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Holiday Rentals in Oak Bluffs

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

The price is AU$1,074
includes taxes & fees
27 July - 28 July
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
The price is AU$4,575
includes taxes & fees
22 July - 23 July
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Island Inn - 2 Bedroom & 2 Bath Townhouse - 47G - Oak Bluffs, MA

10.0 out of 10, Exceptional, (2)
"Property was clean and very accomaditing "
The price is AU$1,473
includes taxes & fees
31 July - 1 Aug
Island Inn - 2 Bedroom & 2 Bath Townhouse - 47G - Oak Bluffs, MA

Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 51G - Oak Bluffs, MA

The price is AU$1,395
includes taxes & fees
25 July - 26 July
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 51G - Oak Bluffs, MA

Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA

9.0 out of 10, Wonderful, (2)
"Great location. Very nice property. The unit was clean but dated in a few areas. Overall, it was perfect for 4 of us visiting for the wknd. "
The price is AU$2,022
includes taxes & fees
3 Aug - 4 Aug
Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA

Island Inn - 2 Bedroom & 2 Bath Townhouse - 42G - Dog-friendly - Oak Bluffs, MA

The price is AU$2,022
includes taxes & fees
3 Aug - 4 Aug
Island Inn - 2 Bedroom & 2 Bath Townhouse - 42G - Dog-friendly - Oak Bluffs, MA

Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA

The price is AU$1,739
includes taxes & fees
28 July - 29 July
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA

Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 46G - Oak Bluffs, MA

The price is AU$1,739
includes taxes & fees
30 July - 31 July
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 46G - Oak Bluffs, MA

Island Inn - 2 Bedroom Townhouse - 40G - Dog-friendly - Oak Bluffs, MA

The price is AU$2,478
includes taxes & fees
15 Aug - 16 Aug
Island Inn - 2 Bedroom Townhouse - 40G - Dog-friendly - Oak Bluffs, MA

Book a Last Minute Cape Escape! Modern, Tranquil Cape home close to town beaches

10.0 out of 10, Exceptional, (8)
"We very much enjoyed the stay and wowed by the beautiful decoration of the house. The owners take good care of this house and they are also very approachable. Thank you for providing such a wonderful environment for our vacation!"
The price is AU$822
includes taxes & fees
29 July - 30 July
Book a Last Minute Cape Escape! Modern, Tranquil Cape home close to town beaches

Standard room one King Bed

7.0 out of 10, Good, (4)
"We enjoyed the convenience of the hotel it was clean and comfortable"
The price is AU$304
includes taxes & fees
22 July - 23 July
Standard room one King Bed

Entire Private Home on Secluded 6 Acre Lot with Water View Near Beaches

10.0 out of 10, Exceptional, (19)
"We had a fantastic stay at this beautiful home for our large family vacation. The house had all the accomodations of home and was centralized to all the places we wanted to visit. Thank you for allowing to stay with you!"
The price is AU$1,487
includes taxes & fees
27 July - 28 July
Entire Private Home on Secluded 6 Acre Lot with Water View Near Beaches

Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach

10.0 out of 10, Exceptional, (32)
"We loved our stay here. It is a private and peaceful location. Christian was a great and responsive host. The house was exactly as listed and very comfortable and clean."
The price is AU$1,618
includes taxes & fees
29 July - 30 July
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach

Beach Vibes & Fun Colors in the Seashell Suite

9.0 out of 10, Wonderful, (14)
"Clean, easy to access, close to beach and restaurants. Owner is very accommodating and communicative. Neighborhood was a perfect home base for a MMA graduation close by. Would recommend!"
The price is AU$592
includes taxes & fees
3 Aug - 4 Aug
Beach Vibes & Fun Colors in the Seashell Suite

Beautiful Private Beach House

10.0 out of 10, Exceptional, (48)
"The property was lovely with amazing views and a comfortable atmosphere. The host was very responsive. It was a great long weekend retreat for a multi-generational family."
The price is AU$5,887
includes taxes & fees
10 Aug - 11 Aug
Beautiful Private Beach House

3 bedroom 2 bath Renovated Ranch with Pond Views on peaceful private 1.5 acre lot in North Falmouth

9.4 out of 10, Exceptional, (3)
"Perfect for us. We have family on Old Main Rd. and a cutter/yawl at Red Brook Harbor. Everything was 2 minutes away. We loved it. Thank you Dr. Leidal"
The price is AU$1,374
includes taxes & fees
27 July - 28 July
3 bedroom 2 bath Renovated Ranch with Pond Views on peaceful private 1.5 acre lot in North Falmouth

Charming 3 bed room with magnificent views & large deck

8.0 out of 10, Very good, (1)
". Great locations. Short walk to numerous restaurants and ferry. "
The price is AU$835
includes taxes & fees
20 Aug - 21 Aug
Charming 3 bed room with magnificent views & large deck

Cape Cod Getaway - close to beaches, shopping and more

10.0 out of 10, Exceptional, (17)
"We had a wonderful stay! Nice property."
The price is AU$1,233
includes taxes & fees
19 Aug - 20 Aug
Cape Cod Getaway - close to beaches, shopping and more

Cape Cod Luxury Waterfront Retreat

10.0 out of 10, Exceptional, (3)
"A terrific property that was top-end from all perspectives. It was clean, spacious, modern and homey. Had a great backyard and plenty of room inside and out to relax alone or with friends and family. We loved the location and will absolutely come back. Thank you!"
The price is AU$5,899
includes taxes & fees
27 July - 28 July
Cape Cod Luxury Waterfront Retreat

Remodeled historical Gosnold Cottage.300 yards to the beach.

10.0 out of 10, Exceptional, (3)
"We had a great stay at this property! It was very clean and spacious for our family of 4. Veterans Beach was within walking distance. The shower was great and my 2 year old loved to run around the property l would definitely stay here again"
The price is AU$1,249
includes taxes & fees
13 Aug - 14 Aug
Remodeled historical Gosnold Cottage.300 yards to the 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.
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Top Oak Bluffs Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Oak Bluffs?

Yes, there are holiday rentals in Oak Bluffs close to Flying Horses Carousel, or you can select a more secluded option if you're looking for a relaxing stay. The shops and waterfront are just a few reasons why tourists like Oak Bluffs. Allow lots of time to check out the beaches and wineries during your visit.

What are some of the best holiday rentals that Oak Bluffs has to offer?

Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C: This highly rated holiday home rental in Oak Bluffs is located on the waterfront, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Another good choice for your trip to Oak Bluffs is MOST CHIC SPOT! Your Martha's Vineyard Getaway!.

How many holiday rentals will I find in Oak Bluffs?

Choose from 264 Expedia holiday rentals in Oak Bluffs for a memorable holiday.

What can I see and do in Oak Bluffs?

Oak Bluffs Town Beach and Inkwell Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Oak Bluffs Fishing Pier. Other places in town to visit include Circuit Avenue and Oak Bluffs Harbor.

What are holiday rentals like in Oak Bluffs?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Bluffs. Holiday rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.