Romantic Hotels & Resorts in Oak Bluffs

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Best Oak Bluffs Romantic Hotels

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, (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
Beach nearby, beach towels

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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Beautiful view of the beach with palm trees

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Frequently asked questions

Searching for romantic hotels in Oak Bluffs?
Are you looking for a romantic holiday? 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 sip a glass of champagne or watch the sunset from your balcony, there are 2 hotels and other accommodation options in Oak Bluffs.
What's the best hotel for a couple going to Oak Bluffs?
Madison Inn is a favourite guest house for couples, and features flat-screen TVs and free WiFi.
How many romantic hotels will we find in Oak Bluffs?
Expedia has 42 romantic Oak Bluffs hotels for you to get cosy 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, take a look at these details about year-round temperatures in Oak Bluffs: The hottest months are usually August and July, with an average temperature of 20°C, while the coldest months are February and January, with an average of 3°C. Average annual precipitation for Oak Bluffs is 1192 mm.
What is there to do in Oak Bluffs?
There’s nothing better than experiencing 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 getaway 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 centre. You can take a ferry and cross the water to see more of the region.