Oak Bluffs Holiday Rentals

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Holiday Rentals in Oak Bluffs

Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C

6.6 out of 10, (15)
"The location was perfect. It is a bit of an older house but it worked for what we needed. The house was clean on arrival and it was very spacious for our kids to run around. My only suggestion would be the it might be time to replace the window until, it was a bit dirty. Other than that everything worked and it was a great mini vacation house."
Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.0 out of 10, (22)
"There were times when the shower in the master bathroom only emitted cold water. The water spigot in the tubs would not turn completely off in bathroom in the hallway. I had trouble with the lockbox. Maybe add more specific directions. It would have been helpful to know that MV transit bus was available at the intersection of the street and County Road."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Spacious colonial home close to town with AC, porches, & W/D

Spacious colonial home close to town with AC, porches, & W/D

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$4,637
includes taxes & fees
11 July - 12 July
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Cozy Beach Cottage

10.0 out of 10, Exceptional, (47)
"Really adorable place that is very well appointed for everything you need"
Cozy Beach Cottage

Updated house close to town and beach with patio, AC, and games

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great location, walking distance to beach, restaurants and shops!"
Updated house close to town and beach with patio, AC, and games

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (325)
"Great stay! Didn't notice it being dated or dirty at all like some reviews said. We loved it!"
The price is AU$1,281
includes taxes & fees
24 July - 25 July
The Club at New Seabury

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (127)
"We love the location of the resort. Easy access to restaurants and beaches. The pool area was great. We went to the indoor pool and hot tub. We feel the unit needed updating. It was clean and accommodating but really old. "
The price is AU$419
includes taxes & fees
31 July - 1 Aug
Sea Mist Resort

Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

8.6 out of 10, Excellent, (39)
"Great place for a summer vacation"
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (95)
"The room is in excellent and clean condition, with easy access to the beach."
The price is AU$541
includes taxes & fees
14 July - 15 July
Beachside Village Resort

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (173)
"Excellent location! Close to the Ferry and downtown !"
InnSeason Resorts Captain's Quarters

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (215)
"We really enjoyed our stay there and can definitely see staying there again. Very convenient to really everything you might want to do. Restaurants nearby as well as the beaches, beautiful places, and boardwalks over the marshes. Also, very clean and comfortable."
Steps to the Ocean! Perfect Location!!!

Gorgeous Cottage steps from the beach

8.4 out of 10, Very good, (15)
"Great place to stay we loved it"
Gorgeous Cottage steps from the beach

Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

2.0 star property
9.4 out of 10, Exceptional, (6)
"Perfect cottage"
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

Charming 3-bedroom house with a pool, AC, WiFi in pleasant East Falmouth

10.0 out of 10, Exceptional, (1)
"Really beautiful place with a lot of space and a very helpful host"
Charming 3-bedroom house with a pool, AC, WiFi in pleasant East Falmouth

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

6.2 out of 10, (18)
"Great location and private beach access. Charming enclave perfect for our weekend getaway."
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

Maushop Property - First Time Available

10.0 out of 10, Exceptional, (39)
"We had a great time at this little cottage! It’s perfect for a few days or a week stay! The house was clean, perfect location for beach walks or shopping at the commons!"
Maushop Property - First Time Available

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (85)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Historic Home across from Monument Beach, Central A/C

10.0 out of 10, Exceptional, (87)
"Great location and easy walk to the beach."
Historic Home across from Monument Beach, Central A/C

Your Oasis Awaits

9.8 out of 10, Exceptional, (38)
"We had a great stay. Nice and close to the beach so my mid 80’s mom could even walk back and forth. and the raw bar on property was the perfect place for an easy meal. Would happily stay again."
Your Oasis Awaits
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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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. Other favourite homes for rent in Oak Bluffs are Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs and MOST CHIC SPOT! Your Martha's Vineyard Getaway!.

How many holiday rentals will I find in Oak Bluffs?

Choose from 260 Expedia holiday rentals in Oak Bluffs for a memorable holiday.

What can I see and do in Oak Bluffs?

Ocean Park and Oak Bluffs Town 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.