Search Holiday Rentals in Oak Bluffs

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Top Holiday Rentals in Oak Bluffs

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (323)
"A great unique and quiet place, very close to Boston."
The Club at New Seabury

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (173)
"Excellent location! Close to the Ferry and downtown !"
InnSeason Resorts Captain's Quarters

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 Rp4.042.709
Rp4.626.881 total
includes taxes & fees
14 Jul - 15 Jul
Sea Mist Resort

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

3.0 star property
9.2 out of 10, Wonderful, (93)
"Wonderful location, nice staff!"
The price is Rp4.889.846
Rp5.596.428 total
includes taxes & fees
1 Jul - 2 Jul
Beachside Village Resort
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 holiday rentals in Oak Bluffs?

Yes, there are holiday rentals in Oak Bluffs close to Flying Horses Carousel, 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 252 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.