The Best Hotels with a Pool in Oak Bluffs, MA from ￥24,216 in 2026

Q: What are some accommodations with pools in Oak Bluffs?

Summercamp : Resort located near Inkwell Beach. Features 3 outdoor tennis courts, a seasonal outdoor pool, and free self parking. MV Surfside Hotel : Offers sun loungers, a pool, and complimentary wireless internet access. Pequot Hotel : Vacation home located near Inkwell Beach. Features sun loungers, a pool, and kitchens. The Island Inn on Martha's Vineyard : Hotel located near Cape Cod Beaches. Offers a snack bar/deli, an indoor pool, and free self parking. Morgan Hotel : Hotel, 2-minute walk from Cape Cod Beaches. Provides a children's pool, a seasonal outdoor pool, and a private beach.

Sunrise striking the houses at Oak Bluffs on Martha's Vineyard, MA.

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Our top choices for Oak Bluffs hotels with a pool

Beautiful Estate with salt water pool & pond with kayaks

Oak Bluffs

￥506,455 total

includes taxes & fees

Jun 11 - Jun 12

Iris Hotel Cape Cod

Falmouth

Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.

￥27,459 total

includes taxes & fees

Jun 21 - Jun 22

Falmouth Inn

Falmouth

Dive into refreshing comfort with an indoor pool oasis that's perfect year-round at this Cape Cod getaway with beach access.

￥24,216 total

includes taxes & fees

Jun 7 - Jun 8

Admiralty Inn & Suites - a Red Collection Hotel

East Falmouth

Dive into year-round aquatic bliss with indoor and seasonal outdoor pools in Cape Cod.

￥25,972 total

includes taxes & fees

Jun 21 - Jun 22

Mariner Motel

Falmouth

Dive into seaside serenity at this coastal retreat with a sun-drenched pool oasis.

￥25,445 total

includes taxes & fees

Jun 8 - Jun 9

ShoreWay Acres Inn & Cape Cod Lodging

Falmouth

Splash into a refreshing escape at this inn with both indoor and seasonal outdoor pools just steps from the beach.

￥29,051 total

includes taxes & fees

Jun 10 - Jun 11

Inn on the Square

Falmouth

Sun-drenched days await at the indoor pool retreat where year-round swimming creates vacation bliss.

￥29,871 total

includes taxes & fees

Jun 8 - Jun 9

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Falmouth Heights Motor Lodge

Falmouth Heights

Splashing summer days at this Falmouth hotel's sparkling pool with loungers and beach bars nearby.

￥34,534 total

includes taxes & fees

Jun 10 - Jun 11

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Choose what matters most at hotels with a pool in Oak Bluffs

Breakfast included

Hot tub

Top Oak Bluffs Hotel Reviews

Sea Crest Beach Resort

6/10 Okay

"Our room was clean although there some areas in the bathroom of concern. The hot tub was colder than the pool. And the public bathrooms by the lobby were very gross with no to"

Harbor View Hotel

6/10 Okay

"The hotel location is beautiful. The building is well kept and clean. The staff was amazing! We loved our room overall but there were a few minor inconveniences: 1. The shower handle kept getting stuck and was hard to turn off. 2. We went in April and the room got very hot at night. You couldn’t change the room thermostat from hot to cold. So they told us to open the windows, which let a bee inside our room because the windows had no nets. "

Frequently asked questions

What are some accommodations with pools in Oak Bluffs?

Summercamp: Resort located near Inkwell Beach. Features 3 outdoor tennis courts, a seasonal outdoor pool, and free self parking. MV Surfside Hotel: Offers sun loungers, a pool, and complimentary wireless internet access. Pequot Hotel: Vacation home located near Inkwell Beach. Features sun loungers, a pool, and kitchens. The Island Inn on Martha's Vineyard: Hotel located near Cape Cod Beaches. Offers a snack bar/deli, an indoor pool, and free self parking. Morgan Hotel: Hotel, 2-minute walk from Cape Cod Beaches. Provides a children's pool, a seasonal outdoor pool, and a private beach.

What is there to see and do in Oak Bluffs?

Surround yourself with nature at Ocean Park and Oak Bluffs Town Beach. During your stay, check out sights such as Circuit Avenue, Oak Bluffs Harbor, and Oak Bluffs Ferry Terminal. The beaches, wineries, and shopping are just some of the things to enjoy while you're in the area.

When is the best time to book a hotel with a pool in Oak Bluffs?

Taking into account the local weather in Oak Bluffs is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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.

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