Holiday Rentals in Oak Bluffs

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Holiday Rentals in Oak Bluffs

Beach nearby, sun-loungers
Steps to the Ocean! Perfect Location!!!
10.0 out of 10, Exceptional, (168)
"The cottage was immaculate. Perfect for our needs. Including location… proximity to the beach, shops and restaurants. Great starting point for everything on the Cape as well as being not that far from Boston, Salem, Worcester and Fall River, everything we wanted to do…. Did I mention immaculate; super clean and fresh smelling. We above all appreciated the communication from the property manager/host. We have stayed with VRBO lots of times and this was the Best"
Steps to the Ocean! Perfect Location!!!
Beach
Steps to the beach with an ocean view,
10.0 out of 10, Exceptional, (96)
"Tom Loved your perfect cottage !!!"
Steps to the beach with an ocean view,
Property grounds
Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths
10.0 out of 10, Exceptional, (7)
"Beautiful home with a great view, right on the ocean. Was very quiet when we went (off season), but will definitely be renting again. Very clean, and had just about everything you would need!"
Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths
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Outdoor dining
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
10.0 out of 10, Exceptional, (157)
"Loved everything about this home! Perfect location. Fantastic views and decorated so beautifully. Would love to stay here again. Highly recommend!"
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Property grounds
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
10.0 out of 10, Exceptional, (11)
"All my wife's children and grandchildren gathered at this lovely home to celebrate her 70th birthday. The home and grounds/neighborhood are simply great and Thomas was a wonderful and responsive host. Since some folks stayed the whole visit and others were only with us for a long weekend, we were thrilled that the dining area accommodated our whole group when necessary, and the kitchen allowed many hands to make light work. The dining table doubled as a spot for the family to gather and...
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Property grounds
Tranquil Oasis: A Beautiful Water-Front Home
10.0 out of 10, Exceptional, (11)
"This house is very nice with lots of room and comfortable beds and furniture. It has everything you need and a beautiful view of the pond. The neighborhood is quiet, but close to a lot of good restaurants and stores. Definitely recommend!"
Tranquil Oasis: A Beautiful Water-Front Home
Fridge, microwave, oven, stovetop
Immaculate Home, 2 Acres, Short Walk To Beach!
10.0 out of 10, Exceptional, (4)
"The property was in a great location, not a long walk to a small beach. We had a group together for a memorial service, and were able to sleep 16. It was clean and pleasant. Some tips: - the seafood store down the road is amazing and cute - if you are a chef type, bring knives - 2 bathrooms for 16 ppl can get a little tight, so make sure your group is ready to share the space, etc. Overall, a great and affordable way to get a group of ppl together for a quiet gathering. Thanks!"
Immaculate Home, 2 Acres, Short Walk To Beach!
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
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, (123)
"Clean, well located, between beach and downtown. Responsive and friendly host."
New House,2 Masters,Steps to Beach, Main Street, Ferry, Central AC, WiFi, Linens
Exterior
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
9.8 out of 10, Exceptional, (63)
"Property is in a great location, walking distance to the shore and a little longer walk or short drive will get you to town with a pub and a few places to eat. Martha’s Vineyard ferry parking is less than ten minutes away with a free shuttle bus that takes you to the ferry. Regina (owner) is right next door and is very friendly and accommodating!!"
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
Beach
Wonderful waterfront getaway with furnished deck, pond access, kayaks & WiFi
9.8 out of 10, Exceptional, (21)
"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
Property grounds
Cozy Cape home with outdoor shower and deck - minutes to beach
9.8 out of 10, Exceptional, (42)
"The cottage is in a quiet location, yet easily accessed off a main road. The place was clean and equipped with comfortable beds. Would recommend and stay here again."
Cozy Cape home with outdoor shower and deck - minutes to beach
Interior
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
9.6 out of 10, Exceptional, (70)
"The apartment was spotless! Open and airy. The host left excellent instructions, and a phone number if needed. We did and he responded immediately and problem resolved. I have only one suggestion. You need more than one mirror It’s located in the bathroom. Need another either in hall or bedroom I would recommend this apartment to anyone"
The price is €656
includes taxes & fees
20 May - 21 May
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
On the beach, white sand
InnSeason Resorts Captain's Quarters
3.5 star property
9.6 out of 10, Exceptional, (143)
"Nice place in a great location"
InnSeason Resorts Captain's Quarters
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
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
Interior
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
Property grounds
Adorable waterfront home w/ boat access & a three-season sunroom
9.2 out of 10, Wonderful, (15)
"On the whole, we enjoyed our stay. Had informed Vacasa that we wouldn’t arrive in Falmouth until midnight 4/25 (as we picked up relatives at Logan Airport), but it hadn’t been forwarded: the sloping entry to the cottage was pitch-dark! In the morning we found garbage cans tipped over, & trash strewn all around the yard —the same thing happening the second night (both times we had to clean up a mess). We requested an hour’s leeway for departing 4/27, which was to have been relayed to local owner;...
Adorable waterfront home w/ boat access & a three-season sunroom
Aerial view
Breathtaking Views with Private Dock & Pool: Summer Special 40% off!
9.2 out of 10, Wonderful, (17)
"We had 3 family birthdays this week & for the 1st time in years we were all together. What made it extra special was this fantastic property & superb location. Maria was so easy to communicate with, it just made everything super smooth. When you get the weather here in the creeks and rivers it is an incredibly enjoyable place to stay, protected kayaking, peaceful yet close to the shops at Mashpee Commons for all the essentials. Thank you Maria."
Breathtaking Views with Private Dock & Pool: Summer Special 40% off!
Seasonal outdoor pool, pool cabanas (surcharge), pool umbrellas
The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (281)
"Good "
The price is €259
includes taxes & fees
19 May - 20 May
The Club at New Seabury
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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.

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

Porch
Summercamp
3.5 star property
9.2 out of 10, Wonderful, (589)
"Great location, clean, staff were very helpful and friendly."
The price is €210
includes taxes & fees
19 May - 20 May
Summercamp
Room, 1 Queen Bed, Non Smoking | View from room
MV Surfside Hotel
2.5 star property
8.8 out of 10, Excellent, (738)
"Accessible "
The price is €266
includes taxes & fees
19 May - 20 May
MV Surfside Hotel
Terrace/patio
Morgan Hotel
2.5 star property
8.4 out of 10, Very good, (113)
"Love the location in Oak bluff. Rates are reasonable. I would like to see a 2nd chair in the room for relaxation, watching tv, "
The price is €329
includes taxes & fees
21 May - 22 May
Morgan 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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Bluffs holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oak Bluffs holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Bluffs holiday rentals we have selected for you start as low as €89 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 holiday 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 holiday.

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 holiday rentals in Oak Bluffs?

Yes, there are holiday rentals in Oak Bluffs close to Oak Bluffs Fishing Pier, 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.

How many holiday rentals will I find in Oak Bluffs?

Choose from 267 Expedia holiday rentals in Oak Bluffs for a memorable holiday.

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 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.

Recent reviews of Oak Bluffs properties
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