Oak Bluffs Vacation Rentals

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Vacation Rentals in Oak Bluffs

Romantic seaside getaway with pool & tennis courts - dog-friendly
Iron/ironing board, WiFi, bed sheets
Romantic seaside getaway with pool & tennis courts - dog-friendly
9.8 out of 10, Exceptional, (36)
"Great location, lots of amenities - pool, fire pits, tennis courts, nearby restaurant. Communication for checking was excellent."
Romantic seaside getaway with pool & tennis courts - dog-friendly
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Fridge, microwave, oven, stovetop
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
8.2 out of 10, Very good, (24)
"Upon entering the property, everything was very clean and welcoming. The rooms were spacious and comfortable. It felt like home. We would definitely book this property again."
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Luxury home with private pool & foosball - near 3 towns & many beaches
Property grounds
Luxury home with private pool & foosball - near 3 towns & many beaches
8.6 out of 10, Excellent, (30)
"I recently stayed in this lovely OB home with my family. It was me and 9 other people, and there was plenty of room for everyone. The photos are accurate. The pool was clean and heated. The house is located in a private, wooded area but conveniently located to OB, Edgartown, the airport and beaches. The interior/furniture were so cozy. The house came equipped with enough plates, dishes, pots, pans, utensil, towels, etc. It would be helpful if the house came with a book of instructions, so we'd...
Luxury home with private pool & foosball - near 3 towns & many beaches
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Cape Winds Resort by VRI Americas
Children's play area - outdoor
Cape Winds Resort by VRI Americas
3.5 star property
8.8 out of 10, Excellent, (393)
"Awesome"
The price is CA $210
CA $240 total
includes taxes & fees
Jun 9 - Jun 10
Cape Winds Resort by VRI Americas
The Club at New Seabury
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas
The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (282)
"Beautiful location with all amenities !"
The price is CA $269
CA $308 total
includes taxes & fees
Jun 5 - Jun 6
The Club at New Seabury
Steps to the Ocean! Perfect Location!!!
Beach nearby, sun loungers
Steps to the Ocean! Perfect Location!!!
10.0 out of 10, Exceptional, (172)
"We enjoyed our stay at Steve's property. The location is wonderful and there are so many things to do on The Cape! There were fairly minor issues that did not detract from the overall stay. And when Steve was contacted he made great efforts to fix the issue(s)."
Steps to the Ocean! Perfect Location!!!
New House,2 Masters,Steps to Beach, Main Street, Ferry, Central AC, WiFi, Linens
Beach nearby, sun loungers, beach towels
New House,2 Masters,Steps to Beach, Main Street, Ferry, Central AC, WiFi, Linens
9.8 out of 10, Exceptional, (125)
"I wanted a place close if not on the beach...walkable to town and a rental that did not require a third party to bring in sheets bedding etc. This place fit all my requirements and the owners made everything easy."
New House,2 Masters,Steps to Beach, Main Street, Ferry, Central AC, WiFi, Linens
Steps to the beach with an ocean view,
Beach
Steps to the beach with an ocean view,
10.0 out of 10, Exceptional, (97)
"A late April getaway was enhanced by staying in this lovely cottage. It was wonderful ‘coming home’ to after a busy day exploring Cape Cod. The cottage is cosy and clean with a well-equipped kitchen - exactly what we want in a vacation rental. Communication was timely and efficient from start to finish. Thank you, Tom!"
Steps to the beach with an ocean view,
InnSeason Resorts Captain's Quarters
On the beach, white sand
InnSeason Resorts Captain's Quarters
3.5 star property
9.6 out of 10, Exceptional, (145)
"Large, comfortable suite, plenty of amenities"
InnSeason Resorts Captain's Quarters
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, (63)
"We very much enjoyed our stay. Scott was a terrific host."
The price is CA $511
CA $1,373 total
includes taxes & fees
Jun 6 - Jun 7
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Harbor-view home with seasonal hot tub, kayaks & fireplace - walk to beach
Balcony
Harbor-view home with seasonal hot tub, kayaks & fireplace - walk to beach
8.8 out of 10, Excellent, (5)
"I sent review comments previously: Dirty blanket was put back in closet Beer bottle in back yard Enjoyed the house/location as we were in town for a wedding."
Harbor-view home with seasonal hot tub, kayaks & fireplace - walk to beach
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
Exterior
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
9.8 out of 10, Exceptional, (65)
"Cute house within walking distance to beach and Main Street. Regina was a wonderful host."
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Exterior
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
9.2 out of 10, Wonderful, (27)
"We really enjoyed our stay. There were a few issues. We couldn’t get in through the front door at all we had to go in through the garage. There were no potholders for cooking. Missing sugar for morning coffee. Napkins and tissues also unavailable. The only major concern that was an inconvenience neither of the bathrooms had heat. Thank you We will definitely be back again"
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Walk to beach 3 bed 2 bath
Interior
Walk to beach 3 bed 2 bath
8.4 out of 10, Very good, (8)
"We had a lovely week. Ask questions of the owner before you get there if there are things that are very important to you."
Walk to beach 3 bed 2 bath
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
Private kitchen
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
9.0 out of 10, Wonderful, (37)
"Very clean and updated property! Conveniently located near the water. Comfortable place for us to rest and give my daughter/husband their space. Recommend this place and look forward to hopefully staying again. My only suggestion is to add dimmable lighting. We felt on stage in the living/kitchen area, bedroom. It would be nice to turn down bathroom light during the night."
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
Wonderful waterfront getaway with furnished deck, pond access, kayaks & WiFi
Beach
Wonderful waterfront getaway with furnished deck, pond access, kayaks & WiFi
9.6 out of 10, Exceptional, (22)
"This beautiful home was clean and well maintained. It was spacious enough for our mid winter getaway with friends- plenty of room to spread out in the living room and the dining room table was big enough for our nightly board games."
Wonderful waterfront getaway with furnished deck, pond access, kayaks & WiFi
Gorgeous Cottage steps from the beach
Beach nearby, sun loungers
Gorgeous Cottage steps from the beach
7.2 out of 10, Good, (5)
"This cottage is charming, quiet, clean, and private. The neighborhood is lovely, and the beach is a few minutes walk down the street."
Gorgeous Cottage steps from the beach
Breathtaking Views with Private Dock & Pool!
Aerial view
Breathtaking Views with Private Dock & Pool!
9.4 out of 10, Exceptional, (18)
"The house is amazing and very convenient with beach / pool stuffs. Good equipment to enjoy"
Breathtaking Views with Private Dock & Pool!
Beautiful bright home with firepit, deck & backyard - walk to beach
Fridge, microwave, oven, stovetop
Beautiful bright home with firepit, deck & backyard - walk to beach
9.6 out of 10, Exceptional, (45)
"Very clean, welcoming"
Beautiful bright home with firepit, deck & backyard - walk to beach
Sunny and Fun Family Cape Cod Vacation Home
Fridge, microwave, oven, stovetop
Sunny and Fun Family Cape Cod Vacation Home
9.6 out of 10, Exceptional, (5)
"Great location, space, and price was perfect."
Sunny and Fun Family Cape Cod Vacation Home
Don't see what you're looking for?
See all available properties in Oak Bluffs
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.

Oak Bluffs Vacation Rental Travel Info

Number of vacation rentals
113
Popular accommodation
Oak Bluffs private vacation homes
Known landmarks
Inkwell Beach, Falmouth Heights Beach and Oak Bluffs Town Beach
International airport
Vineyard Haven, MA (MVY-Martha's Vineyard)

Other types of properties in Oak Bluffs you may be interested in

Summercamp
Porch
Summercamp
3.5 star property
9.2 out of 10, Wonderful, (627)
"Wonderful staff, very friendly, Came in that greeted me by my first name, lived that. Felt at home Very clean, very well decorated. Loved everything about this place"
The price is CA $353
CA $394 total
includes taxes & fees
Jun 6 - Jun 7
Summercamp
MV Surfside Hotel
Room, 1 Queen Bed, Non Smoking | View from room
MV Surfside Hotel
2.5 star property
8.8 out of 10, Excellent, (741)
"Hotel was the best location you could dream of. Walking distance from the ferry and bus stops,walking location, to the beach, dining and shopping districts. The park ,boardwalk and beaches were relatively close as well. The staff was very professional and helpful. 🌷They were beyond nice. The hotel is also very clean. The coffee in the lobby is the best way to start the day. We are very happy and will be back soon."
The price is CA $358
CA $436 total
includes taxes & fees
Jun 5 - Jun 6
MV Surfside Hotel
Pequot Hotel
Beach nearby, beach towels
Pequot Hotel
3.0 star property
9.4 out of 10, Exceptional, (453)
"Pequot Hotel was clean and great location (a block away from beach, several blocks from main street with restaurants and shops). The room we stayed (Middle Queen Room) was so tiny. It just enough to put the queen bed in. No fridge or microwave."
The price is CA $326
CA $364 total
includes taxes & fees
Jun 5 - Jun 6
Pequot Hotel
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.

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Bluffs vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Bluffs vacation rentals we have selected for you start as low as CA $210 per night. Entering your travel dates in the search wizard 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. 

Frequently asked questions

Can I find vacation rentals in Oak Bluffs?

Yes, you can find vacation rentals in Oak Bluffs near Oak Bluffs Fishing Pier, 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?

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower: This vacation home rental outside of Oak Bluffs offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals will I find in Oak Bluffs?

Choose from 271 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.

Recent reviews of Oak Bluffs properties
Expedia verified reviews

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

5/5 Excellent
Perfect Family Vacation!
"Chimene's property was absolutely perfect in every way. From the fenced in yard, to the location of the home and everything in-between. It fit our family perfectly. It is a short distance walk to downtown. We even walked to the ginger bread houses, as well as the park for the kids. The fenced in yard was perfect for our kids and dogs to play in. Communication with Chimene was very easy and John was on site and so nice. He took extra time in making sure the outside yard was ready for us. We will definitely be back!! It made our MDW perfect!"
A verified traveller stayed at Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs
Posted 1 day ago
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs