The Best Hotels with a Pool in Chilmark, MA from ₩261,483 in 2026

Q: What are some accommodations with pools in Chilmark?

Iris Hotel Cape Cod : Features complimentary wireless internet access, a pool, and Smart TVs. Sea Crest Beach Resort : Hotel located near Cape Cod Beaches. Offers a snack bar/deli, an indoor pool, and free self parking. Vineyard Harbor Motel - Private Beach : Hotel, 2-minute walk from Cape Cod Beaches. Provides a children's pool, a seasonal outdoor pool, and a private beach. Falmouth Inn : Hotel located near Cape Cod Beaches. Offers daily, a pool, and free self parking. AutoCamp Cape Cod : Hotel located near Cape Cod Beaches. Provides a seasonal outdoor pool, an indoor pool, and daily.

A dock with boats, a small wooden structure, and a forested shoreline.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Chilmark Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Chilmark hotels with a pool

Hampton Inn by Hilton New Bedford/Fairhaven

Fairhaven

Seasonal outdoor pool beckons with refreshing waters, offering a perfect retreat from warm summer days in New Bedford.

₩261,483 total

includes taxes & fees

Aug 2 - Aug 3

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.

₩302,733 total

includes taxes & fees

Jul 20 - Jul 21

Classic Double Room | Bathroom | Combined shower/tub, free toiletries, hair dryer, towels

Mariner Motel

Falmouth

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

₩324,219 total

includes taxes & fees

Jul 16 - Jul 17

Iris Hotel Cape Cod

Falmouth

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

₩415,139 total

includes taxes & fees

Jul 19 - Jul 20

Inn on the Square

Falmouth

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

₩438,696 total

includes taxes & fees

Jul 21 - Jul 22

Admiralty Inn & Suites - a Red Collection Hotel

East Falmouth

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

₩325,206 total

includes taxes & fees

Aug 11 - Aug 12

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.

₩375,674 total

includes taxes & fees

Jul 16 - Jul 17

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.

₩395,882 total

includes taxes & fees

Jul 12 - Jul 13

View all properties

Choose what matters most at hotels with a pool in Chilmark

Breakfast included

4 stars

Top Chilmark Hotel Reviews

Iris Hotel Cape Cod

10/10 Excellent

"The breakfast place was empty and we waited for some time, but nothing was worth it. "

Green Harbor Waterfront Lodging

8/10 Good

"I wasn't traveling with any pets, but I know they are welcomed. There were several pups just outside the pool area who seemed so happy to be with their owners. We had a slight issue with check-in, which was entirely my fault. I had the wrong dates in my calendar. On Friday, July 3, there were no rooms available, but the person manning the front desk (Sam) called to secure the last room at a sister property. He went above and beyond to make sure we didn't have to go back over the bridge and endure more traffic both ways. "

Frequently asked questions

What are some accommodations with pools in Chilmark?

Iris Hotel Cape Cod: Features complimentary wireless internet access, a pool, and Smart TVs. Sea Crest Beach Resort: Hotel located near Cape Cod Beaches. Offers a snack bar/deli, an indoor pool, and free self parking. Vineyard Harbor Motel - Private Beach: Hotel, 2-minute walk from Cape Cod Beaches. Provides a children's pool, a seasonal outdoor pool, and a private beach. Falmouth Inn: Hotel located near Cape Cod Beaches. Offers daily, a pool, and free self parking. AutoCamp Cape Cod: Hotel located near Cape Cod Beaches. Provides a seasonal outdoor pool, an indoor pool, and daily.

What is there to see and do in Chilmark?

The picturesque setting of Menemsha Beach and Edys Island showcase the area's natural beauty. During your stay, check out sights such as Chilmark Town Hall, Chilmark Public Library, and Chilmark Chocolates.

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

Taking into account the local weather in Chilmark can help you maximize your time at the pool during your trip. 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 Chilmark is 50 inches.

Explore a world of travel with Expedia

More ways to book

Book Hotels with a Pool in Chilmark on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Chilmark Hotels with a Pool

Our top choices for Chilmark hotels with a pool