Find Romantic Hotels in Oak Bluffs, MA

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Pick from 3 Oak Bluffs Romantic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

MV Surfside Hotel
Exterior

MV Surfside Hotel

2.5 star property
8.8 out of 10, Excellent, (805)
"We had an excellent stay! The staff made it very enjoyable and gave us recommendations when we needed to switch our plans around due to weather. We will definitely be back!"
MV Surfside Hotel
Pequot Hotel
Exterior

Pequot Hotel

3.0 star property
9.4 out of 10, Exceptional, (498)
"The best staff "
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.
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Frequently asked questions

Searching for romantic hotels in Oak Bluffs?
Are you in need of a romantic getaway? Couples choose Oak Bluffs for its beaches and wineries. During your trip, you may want to go for a sunset stroll along the water with your love at Oak Bluffs Town Beach, Inkwell Beach, or Seaview Beach. Whether you want to soak in a spa tub or enjoy a decadent breakfast in bed, there are 2 hotels and other accommodations in Oak Bluffs.
How many romantic hotels can we expect to find in Oak Bluffs?
Expedia has 42 romantic Oak Bluffs hotels for you to get cozy in.
When is the best time of year for a romantic getaway to Oak Bluffs?
If you’re looking forward to lots of outings with your partner, check out these details about year-round temperatures in Oak Bluffs: The hottest months are usually August and July with an average temp of 68°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Oak Bluffs is 47 inches.
What is there to do in Oak Bluffs?
There’s nothing better than wandering around a new place with your sweetheart, so consider taking time to discover all there is to see and do in Oak Bluffs. Couples looking for a little of everything will enjoy Oak Bluffs for its shopping, wineries, and beaches. Circuit Avenue, Ocean Park, and Flying Horses Carousel are worth a stop when you’re out and about.
What's the best way to get to Oak Bluffs and around town during my romantic getaway?
These transportation options in Oak Bluffs might help your romantic trip go off without a hitch: Make your way to Oak Bluffs with a flight to Vineyard Haven, MA (MVY-Martha’s Vineyard), which is the closest major airport located 5.2 mi (8.3 km) from the city center. You can ride a ferry across the water to see more of the region.