Oak Bluffs Vacation Rentals

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Check prices for these dates

Tonight
Jun 19 - Jun 20
Tomorrow
Jun 20 - Jun 21
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

Vacation Rentals in Oak Bluffs

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Interior

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

9.6 out of 10, Exceptional, (78)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is ￥61,988
￥100,500 total
includes taxes & fees
Jun 29 - Jun 30
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Oak Bluffs - Quiet neighborhood
Terrace/patio

Oak Bluffs - Quiet neighborhood

9.2 out of 10, Wonderful, (36)
"Very nice property, cute backyard set up. Close to downtown OB and Tony's market for grocery needs. Second time staying here and would stay again"
Oak Bluffs - Quiet neighborhood
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Terrace/patio

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

6.0 out of 10, (21)
"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 quintessential MV home. Now booking for 2025!
Fridge, microwave, oven, stovetop

The quintessential MV home. Now booking for 2025!

9.8 out of 10, Exceptional, (53)
"Just a quick 4 minute drive to downtown. Listing was accurate and place was clean!"
The quintessential MV home. Now booking for 2025!
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
Exterior

Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

7.4 out of 10, Good, (3)
"We had a wonderful early-June weekend stay at this charming house minutes walk from town. Highlights were reading on the rocking chair on the deck and playing games in the screened-in porch. Everything looks just like in the listing - charming, warm, like staying at your grandpa's beach house. There were a few bumps - the listed dryer was in a locked shed, a faucet wasn't working - but our sense was this is a new listing and details are still being ironed out. None of that interfered with our...
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
Relax & Renew at this Luxury Villa with Heated Pool & Hot Tub, Tennis, Firepit!
A heated pool

Relax & Renew at this Luxury Villa with Heated Pool & Hot Tub, Tennis, Firepit!

9.4 out of 10, Exceptional, (13)
"House was amazing and close to town. It’s always great to find a place with a pool on that island."
Relax & Renew at this Luxury Villa with Heated Pool & Hot Tub, Tennis, Firepit!
Private Family Home, Heated Pool, Hottub, 5 BR.4.5 bath, WiFi, AC. NO PETS.
Interior

Private Family Home, Heated Pool, Hottub, 5 BR.4.5 bath, WiFi, AC. NO PETS.

10.0 out of 10, Exceptional, (57)
"Stay was fun"
Private Family Home, Heated Pool, Hottub, 5 BR.4.5 bath, WiFi, AC. NO PETS.
Cozy getaway in a central location w/ a full kitchen & furnished deck
Beach

Cozy getaway in a central location w/ a full kitchen & furnished deck

6.8 out of 10, (22)
"The furniture and amenities provided were good"
Cozy getaway in a central location w/ a full kitchen & furnished deck
Make Lasting Memories In This Adorable Vineyard Cottage!
Exterior

Make Lasting Memories In This Adorable Vineyard Cottage!

9.8 out of 10, Exceptional, (143)
"Easy to find, clean, easy check in and put. Super cute cottage. "
Make Lasting Memories In This Adorable Vineyard Cottage!
The Club at New Seabury
Private beach nearby, beach bar

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (321)
"A great unique and quiet place, very close to Boston."
The Club at New Seabury
InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (172)
"Nice hotel close to the beach! Well appointed kitchenette & nice comfortable suite with two full baths and jacuzzi tub. Exceeded expectations "
InnSeason Resorts Captain's Quarters
Sea Mist Resort
Indoor pool, outdoor pool, sun loungers

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (124)
"Great place just had another family staying above our room that was very noisy the last night we were there"
The price is ￥27,797
￥31,813 total
includes taxes & fees
Jun 24 - Jun 25
Sea Mist Resort
Southcape Resort Mashpee a Ramada by Wyndham
Exterior

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (199)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham
Beachside Village Resort
Seasonal outdoor pool

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (93)
"This place is adorable. Very comfortable, clean, cozy and located right across from the beach. Unfortunately they were doing construction in beach parking lot but still enjoyed our stay very much. Will definitely rent there again. "
Beachside Village Resort
Steps to the Ocean! Perfect Location!!!
Beach nearby, sun loungers

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (212)
"Loved our 3 night stay in this cozy little cottage. Close to everything, including the ferry and beach. Hope to be back!"
Steps to the Ocean! Perfect Location!!!
Steps to the beach with an ocean view,
On the beach, sun loungers, beach towels

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (119)
"To stay a block from the beach and look out the window at the water is the ultimate vacation! Even in winter this place is warm and inviting! The hosts are caring and communicative - just the best! This cottage lets you do just that"
Steps to the beach with an ocean view,
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
Outdoor dining

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

2.0 star property
9.6 out of 10, Exceptional, (4)
"Perfect cottage"
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel crib

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

10.0 out of 10, Exceptional, (83)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Newly renovated 2BR house, FREE CAR w/beach sticker, pet friendly, sleeps 8
Living area

Newly renovated 2BR house, FREE CAR w/beach sticker, pet friendly, sleeps 8

Newly renovated 2BR house, FREE CAR w/beach sticker, pet friendly, sleeps 8
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Beach nearby, sun loungers, beach towels

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

9.6 out of 10, Exceptional, (64)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
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 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?

Oak Bluffs - Quiet neighborhood: Visitors give good reviews to this Oak Bluffs vacation home rental, which offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable 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. Another good choice for your trip to Oak Bluffs is Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs.

How many vacation rentals will I find in Oak Bluffs?

Choose from 253 Expedia vacation rentals in Oak Bluffs for a memorable vacation.

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 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.