Oak Bluffs Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Oak Bluffs

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

Oak Bluffs
6.4 out of 10, (31)
"indoor and outdoor comfortable space"
United States
Delores C.
Tranquil Home with Private Deck - Walk to Beaches and Downtown 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

Oak Bluffs
6.6 out of 10, (25)
"The home was nice, a little outdated, but great for a family.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
Fridge, microwave, oven, stovetop
The quintessential MV home. Now booking for 2026!

The quintessential MV home. Now booking for 2026!

Oak Bluffs
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.

Oak Bluffs
9.4 out of 10, Exceptional, (91)
"Location, the water view, delicious restaurants nearby. Apt was comfy, clean. For 1 night only used the fridge. "
United States
Brenda M.
The price is ￥41,772
￥77,074 total
includes taxes & fees
Nov 14 - Nov 15
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!

Oak Bluffs
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 ￥84,733
￥186,713 total
includes taxes & fees
Nov 14 - Nov 15
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
Oak Bluffs
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

Oak Bluffs
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

Edgartown
9.8 out of 10, Exceptional, (81)
"Great stay ..."
United States
Hayley H.
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts
Smart TV
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Oak Bluffs
9.4 out of 10, Exceptional, (88)
"We loved our stay! It was the perfect location, loved the view, it was sparce but clean. Check in/out was easy and owner was responsive. "
United States
Tracy M.
The price is ￥41,596
￥76,749 total
includes taxes & fees
Nov 14 - Nov 15
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Private beach nearby, beach bar
The Club at New Seabury

The Club at New Seabury

3.5 star property
Mashpee
9.0 out of 10, Wonderful, (336)
"Great stay! Didn't notice it being dated or dirty at all like some reviews said. We loved it!"
United States
Rachael
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.

East Falmouth
10.0 out of 10, Exceptional, (88)
"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 ￥60,027
￥157,234 total
includes taxes & fees
Dec 8 - Dec 9
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
Falmouth Heights
9.8 out of 10, Exceptional, (192)
"Absolutely beautiful room amenities and view. Hands down the best place we have ever stayed at on the Cape. Definitely going back!!"
United States
Keith
InnSeason Resorts Captain's Quarters
Indoor pool, outdoor pool, sun loungers
Sea Mist Resort

Sea Mist Resort

3.0 star property
Mashpee
8.6 out of 10, Excellent, (140)
"We had a fabulous visit!"
United States
Joelle
Sea Mist Resort
Beach nearby, sun loungers
Steps to the Ocean! Perfect Location!!!

Steps to the Ocean! Perfect Location!!!

Barnstable
10.0 out of 10, Exceptional, (231)
"I absolutely loved my stay at this charming cottage in Hyannis! The place was cozy, spotless, and beautifully maintained. A perfect mix of comfort and Cape Cod charm. The location was great, close to the beach and local shops, yet quiet enough to relax and unwind."
United States
Maria
Steps to the Ocean! Perfect Location!!!
Outdoor dining
Newly Renovated Near Amazing Sunset Beach

Newly Renovated Near Amazing Sunset Beach

Falmouth
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
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

West Tisbury
9.0 out of 10, Wonderful, (35)
"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
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

East Falmouth
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
Falmouth
9.4 out of 10, Exceptional, (101)
"Very clean and quiet place to relax. Very friendly and professional! We will come back!"
United States
Emmanuelle Loriot
Beachside Village Resort
Beach nearby, sun loungers, beach towels
Steps from Marina, beach, restaurants!

Steps from Marina, beach, restaurants!

Wareham
9.8 out of 10, Exceptional, (12)
"Beautiful space, wonderful location, amazing host. If I could give 100 stars I would! "
United States
Jaimie
The price is ￥13,727
￥36,155 total
includes taxes & fees
Nov 19 - Nov 20
Steps from Marina, beach, restaurants!
On the beach, sun loungers, beach towels
Steps to the beach with an ocean view,

Steps to the beach with an ocean view,

Barnstable
10.0 out of 10, Exceptional, (139)
"Great stay."
United States
Richard D.
Steps to the beach with an ocean view,
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

Faraway Martha's Vineyard

Faraway Martha's Vineyard

10/10 Excellent
"Friendly staff, clean room (housekeeping did an awesome job!), convenient parking, great location - walking distance to cafes, shops, restaurants, waterfront, etc, easy check-in/out. HIGHLY RECOMMENDED!"
John 3-night trip
Posted 2 days ago
Faraway Martha's Vineyard

Find out more about Oak Bluffs

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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?

MOST CHIC SPOT! Your Martha's Vineyard Getaway!: Visitors give good reviews to this Oak Bluffs vacation home rental, which is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 Updated house close to town and beach with patio, AC, and games and Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs.

How many vacation rentals will I find in Oak Bluffs?

Choose from 260 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 Flying Horses Carousel.

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.