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

6.2 out of 10, (17)
"This property has not been well cared for or cleaned. Arrived to a very musty/moldy smell, trash outside, the walls were streaked with dead bug guts and then the stove didn't work!! It was a step above camping. You get what you pay for!"
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

THE PARK ESTATE! Your Martha's Vineyard Getaway!

9.8 out of 10, Exceptional, (16)
"The Park Estate is absolutely a phenomenal property. This estate has EVERYTHING you could ever want and need! The estate is well appointed, wonderfully located to travel throughout the area and the host, grounds keeper and everyone we communicated with was so kind, accessible and very informative. How we were so blessed to be able to rent this beautiful property at the last minute. It truly was fate. We look forward to future opportunities to stay here!"
THE PARK ESTATE! Your Martha's Vineyard Getaway!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

The price is NZ$1,042
includes taxes & fees
28 July - 29 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 NZ$4,941
includes taxes & fees
24 July - 25 July
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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 Club at New Seabury

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (131)
"The rooms are spacious if somewhat dated. Good value. "
The price is NZ$517
includes taxes & fees
27 July - 28 July
Sea Mist Resort

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 NZ$631
includes taxes & fees
28 July - 29 July
Beachside Village Resort

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (174)
"Excellent location! Close to the Ferry and downtown !"
InnSeason Resorts Captain's Quarters

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..

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (216)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (123)
"was very nice, clean cozy and close to beach...LOVED IT!"
Steps to the beach with an ocean view,

Great Home Close to Craigville Beach

10.0 out of 10, Exceptional, (2)
"My friends and I had an amazing stay! The house was clean and the check in process was extremely easy. Also located super close to the beach!"
Great Home Close to Craigville Beach

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

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

8.4 out of 10, Very good, (20)
"So turn key and perfect for Month, Joy is an exceptional host and I’d recommend her place anytime"
The price is NZ$374
includes taxes & fees
27 July - 28 July
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

8.8 out of 10, Excellent, (33)
"Great spot for a get away. Private with easy access to activities."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

Relax & Unwind at this Adorable and very private 1 bedroom 1 bath studio

10.0 out of 10, Exceptional, (2)
"Just as described, the location of the property is surrounded by nature and lush with plants and animals. Lots of beautiful birds such as cardinals and blue jays. Perfect amount of space for 2 people. One of the best parts of the stay was the large walk in shower, and the robes provided were a perfect touch. Overall a very cozy and secluded getaway perfect for a long weekend. "
Relax & Unwind at this Adorable and very private 1 bedroom 1 bath studio

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

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (200)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham

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

5.6 out of 10, (21)
"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
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.