Oak Bluffs Vacation Rentals

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Vacation 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"The home was nice, a little outdated, but great for a family.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 It’s shabby- a little bit of a smell and outdated furniture.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
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!
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
$446 nightly
The price is $498
Nov 4 - Nov 5
Total with taxes and fees
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.
$1,085 nightly
The price is $1,212
Nov 4 - Nov 5
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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
Exterior
Spacious home in central location with beautiful patio, pool table, W/D, & AC
Spacious home in central location with beautiful patio, pool table, W/D, & AC
2.0 star property
10.0 out of 10, Exceptional, (4)
"Absolutely loved our stay at this Oak Bluffs home! The location was perfect—just a 20-minute walk to downtown—and the house itself was warm, inviting, and beautifully laid out with an open-air feel. The kitchen was fully stocked, the beds were super comfortable, and the outdoor shower was a wonderful bonus. We felt completely relaxed and free during our stay. Can’t wait to come back next summer!"
United States
Monica D.
Spacious home in central location with beautiful patio, pool table, W/D, & AC
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
$151 nightly
The price is $173
Nov 4 - Nov 5
Total with taxes and fees
The Club at New Seabury
5 bedrooms, desk, iron/ironing board, travel crib
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.
$901 nightly
The price is $1,031
Nov 30 - Dec 1
Total with taxes and fees
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, sun 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
$145 nightly
The price is $167
Nov 8 - Nov 9
Total with taxes and fees
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!!!
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
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
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
Beach nearby, sun loungers, beach towels
Steps from Marina, beach, restaurants!
Steps from Marina, beach, restaurants!
9.8 out of 10, Exceptional, (12)
"Property was as described. This was only a quick stay & wish we had a longer visit. Location was great with lots to do. Owner was available to answer any questions "
United States
kristen b.
$210 nightly
The price is $235
Nov 10 - Nov 11
Total with taxes and fees
Steps from Marina, beach, restaurants!
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

Summercamp

Summercamp

10/10 Excellent
"Amazing staff and I love the complementary coffee experience "
Paola 1-night trip
Posted 15 hours ago
Summercamp

Find out more about Oak Bluffs

Everything you need to know about Oak Bluffs vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Bluffs vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Bluffs vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oak Bluffs vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Bluffs. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oak Bluffs in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $167 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oak Bluffs rentals

At Expedia, we put the best Oak Bluffs vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oak Bluffs rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Bluffs vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Bluffs. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Oak Bluffs?

Yes, you can find vacation rentals in Oak Bluffs near Flying Horses Carousel, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals in Oak Bluffs?

Cozy getaway in a central location w/ a full kitchen & furnished deck: Visitors give good reviews to this Oak Bluffs vacation home rental, which 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 you can cook with friends or family. Other favorite 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 vacation rentals will I find in Oak Bluffs?

Choose from 261 Expedia vacation rentals in Oak Bluffs for a memorable vacation.

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 vacation rentals like in Oak Bluffs?

Vacation rentals are private accommodations you can reserve for several days or longer in Oak Bluffs. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.