Oak Bluffs Holiday Rentals

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Tonight
1 Nov - 2 Nov
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2 Nov - 3 Nov
Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov

Holiday Rentals in Oak Bluffs

Beach
Cozy getaway in a central location w/ a full kitchen & furnished deck
Cozy getaway in a central location w/ a full kitchen & furnished deck
6.6 out of 10, (24)
"The home was nice, a little outdated, but great for a family. Unfortunately it does not have AC and when we arrived we found 2 fans were broken. We immediately contacted Vacasa who said they would send maintenance. While waiting for maintenance, we also noticed within the first hour that one of the dining chair backs was broken/not attached, one of the bed posts fell off as it was not attached, and the fan in one of the bathrooms was stuck on. We planned to notify maintenance when they came but...
United States
Dawn R.
Cozy getaway in a central location w/ a full kitchen & furnished deck
Exterior
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
6.4 out of 10, (31)
"It is an old home that has had no updates. It’s shabby- a little bit of a smell and outdated furniture. That being said, it has everything you need and is a good location on the island, especially if you are driving. It was a deal compared to everything else around and was somehow available during summer with less than 2 months before we booked."
United States
Myrtle A.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Interior
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
9.4 out of 10, Exceptional, (91)
"The apartment was awesome with great views of the ocean and a very convenient location to the ferry and shopping."
United States
Stephen
The price is HK$2,098
HK$3,871 total
includes taxes & fees
2 Nov - 3 Nov
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
10.0 out of 10, Exceptional, (7)
"This home is truly that, a welcoming escape nestled in the woods. It’s elevated beach-style furnishings feel hand-picked. We traveled with a 14 month old — the house had high-quality baby must haves, pack and play and high chair. We had the pleasure of a responsive host and caretaker. Close to trails, YMCA and the island’s top attractions … !highly recommend!"
United States
Kerry-Ann H.
The price is HK$4,274
HK$9,417 total
includes taxes & fees
2 Nov - 3 Nov
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Fridge, microwave, oven, stovetop
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
10.0 out of 10, Exceptional, (71)
"Large home with plenty of room for extended family. Located in quiet neighborhood close to Oak Bluffs, would highly recommend."
United States
Eileen P.
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
Fridge, microwave, oven, stovetop
The quintessential MV home. Now booking for 2026!
The quintessential MV home. Now booking for 2026!
9.8 out of 10, Exceptional, (55)
"Beautiful home on quiet street within walking distance to Oak Bluffs. Well equipped kitchen and comfy family room. Beautiful primary suite with huge modern bathroom. Carrington was an excellent host and very responsive to anything that came up. "
United States
Jenny D.
The quintessential MV home. Now booking for 2026!
Property grounds
Updated house close to town and beach with patio, AC, and games
Updated house close to town and beach with patio, AC, and games
2.0 star property
9.8 out of 10, Exceptional, (6)
"Great place, would stay again. Comfortable beds, walking distance to tons, nicely decorated. Had everything we needed."
United States
Margaret C.
Updated house close to town and beach with patio, AC, and games
Outdoor dining
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
8.2 out of 10, Very good, (40)
"Great property as it is located so close to Oak Bluffs. Plenty of space for the four of us who when there."
United States
Jennifer S.
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Property grounds
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts
9.8 out of 10, Exceptional, (81)
"Great stay ..."
United States
Hayley H.
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts
Property grounds
Beautiful Estate with salt water pool & pond with kayaks
Beautiful Estate with salt water pool & pond with kayaks
2.5 star property
Beautiful Estate with salt water pool & pond with kayaks
Private beach nearby, beach bar
The Club at New Seabury
The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (336)
"Nice amenities. "
United States
William
The Club at New Seabury
5 bedrooms, desk, iron/ironing board, travel cot
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Coastal chic meets French Provençal in this newly renovated oceanfront home.
10.0 out of 10, Exceptional, (87)
"This is a lovely property for a family beach vacation! The property has a wonderful view of the ocean, easy access to a beach, and is close to many great restaurants and things to do. Our host was very responsive and accommodating throughout our stay. I would highly recommend. "
United States
Andrew H.
The price is HK$3,100
HK$8,013 total
includes taxes & fees
30 Nov - 1 Dec
Coastal chic meets French Provençal in this newly renovated oceanfront home.
On the beach, white sand
InnSeason Resorts Captain's Quarters
InnSeason Resorts Captain's Quarters
3.5 star property
9.8 out of 10, Exceptional, (189)
"Great place to stay. Close to Island Queen ferry and right by the beach. Would definitely go back!"
United States
Matt
InnSeason Resorts Captain's Quarters
Indoor pool, outdoor pool, pool loungers
Sea Mist Resort
Sea Mist Resort
3.0 star property
8.6 out of 10, Excellent, (140)
"We had a fabulous visit!"
United States
Joelle
The price is HK$1,299
HK$1,487 total
includes taxes & fees
8 Nov - 9 Nov
Sea Mist Resort
Beach nearby, sun-loungers
Steps to the Ocean! Perfect Location!!!
Steps to the Ocean! Perfect Location!!!
10.0 out of 10, Exceptional, (230)
"Perfect for a couple and two kids"
United States
Shelly R.
Steps to the Ocean! Perfect Location!!!
Seasonal outdoor pool
Beachside Village Resort
Beachside Village Resort
3.0 star property
9.2 out of 10, Wonderful, (100)
"Wonderful location, nice staff!"
United States
Claire
Beachside Village Resort
Outdoor dining
Newly Renovated Near Amazing Sunset Beach
Newly Renovated Near Amazing Sunset Beach
9.8 out of 10, Exceptional, (73)
"The house is beautiful. It looks just like the pictures. The area around the house is very safe and quiet. The owners are very responsive. They even provided beach towels (which might not be in the description). "
United States
Debbie B.
Newly Renovated Near Amazing Sunset Beach
Exterior
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
10.0 out of 10, Exceptional, (112)
"The place was beautiful, clean, spacious and the perfect location. There were so many options, from hanging out on the porch, by the fire, on the water front, or inside around the upstairs living room/billiards area downstairs. The owner was an amazing communicator, as she answered all of my questions promptly. I highly recommend this place to anyone!Thank you for an awesome and memorable stay! "
United States
natalia A.
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
On the beach, sun-loungers, beach towels
Steps to the beach with an ocean view,
Steps to the beach with an ocean view,
10.0 out of 10, Exceptional, (137)
"Great stay."
United States
Richard D.
Steps to the beach with an ocean view,
Terrace/patio
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
9.0 out of 10, Wonderful, (34)
"The peaceful woodland setting is just beautiful! Enjoyed a quiet stay in this spacious one bedroom house. The porch wraps around entire house and gave our morning coffee and breakfast a very special vacation feel."
United States
Maryann B.
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
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

Mansion House Inn And Spa

Mansion House Inn And Spa

10/10 Excellent
"Great staff.Very helpful and informative.Convenient location.Room was very clean.Would definitely stay again."
Timothy 3-night trip
Posted 2 days ago
Mansion House Inn And Spa

Find out more about Oak Bluffs

Search for holiday rentals in Oak Bluffs on Expedia! You can easily find your home rentals, villas, holiday apartments in Oak Bluffs using one of the methods below:

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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?

Cozy getaway in a central location w/ a full kitchen & furnished deck: This highly rated holiday home rental in Oak Bluffs offers a patio, a garden and free WiFi to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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 261 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.