The Best Hotels with a Pool in Oak Bluffs, MA from ₩205,375 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 : Provides sun loungers, a pool, and complimentary wireless internet access. Pequot Hotel : Vacation home located near Inkwell Beach. Offers sun loungers, a pool, and kitchens. The Island Inn on Martha's Vineyard : Hotel, 2-minute walk from Cape Cod Beaches. Features a children's pool, a seasonal outdoor pool, and a private beach. Morgan Hotel : Hotel located near Cape Cod Beaches. Offers a snack bar/deli, an indoor pool, and free self parking.

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

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.

₩251,457 total

includes taxes & fees

May 31 - Jun 1

Iris Hotel Cape Cod

Falmouth

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

₩223,174 total

includes taxes & fees

Jun 1 - Jun 2

Inn on the Square

Falmouth

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

₩261,964 total

includes taxes & fees

Jun 2 - Jun 3

Seasonal outdoor pool, open 8:00 AM to 7:30 PM, pool umbrellas

The Harborside Inn

Edgartown

Float in blissful style at a seasonal outdoor pool, where relaxation meets Martha's Vineyard magic.

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.

₩212,878 total

includes taxes & fees

Jun 2 - Jun 3

Green Harbor Waterfront Lodging

East Falmouth

Seasonal waterfront pool creates summer magic at this Cape Cod retreat with a garden terrace.

₩231,762 total

includes taxes & fees

Jun 1 - Jun 2

Mariner Motel

Falmouth

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

₩205,375 total

includes taxes & fees

Jun 3 - Jun 4

Admiralty Inn & Suites - a Red Collection Hotel

East Falmouth

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

₩242,018 total

includes taxes & fees

Jun 1 - Jun 2

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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

10/10 Excellent

"The resort is beautiful the area is beautiful. The food at the lantern room was great. The views, beach, and pools were great. It is a great family resort. The rooms could use a little love. Our room wasn’t ready until approximated 5pm. Check-in was 4pm."

Admiralty Inn & Suites - a Red Collection Hotel

2/10 Terrible

"Horrible. Unusable pillows. Defective room with poor workmanship. Couldn’t close bathroom door. Noisey aircon from adjoining rooms all night. Big floodlights light up the room all night due to insufficient curtains. Worst night sleep in many years. The owners obviously never spent a night in one of their rooms."

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

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, Flying Horses Carousel, and Oak Bluffs Harbor. 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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