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Find Hotels with a Pool in Chilmark, MA

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Check availability on Chilmark Hotels with a Pool

Tonight
Dec 7 - Dec 8
Tomorrow
Dec 8 - Dec 9
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Top Chilmark Hotels with a Pool

Outdoor pool, a heated pool
Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool

Chilmark
9.6 out of 10, Exceptional, (21)
"We loved this property and would love to return!"
United States
Clifford L.
The price is ￥45,822
￥71,483 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Cozy efficiency apartment/heated pool
Indoor pool
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3.0 star property
Falmouth
8.6 out of 10, Excellent, (154)
"great bedroom "
United States
Jessica
The price is ￥14,679
￥16,801 total
includes taxes & fees
Dec 11 - Dec 12
Iris Hotel Cape Cod
Indoor pool, seasonal outdoor pool
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 star property
North Falmouth
8.0 out of 10, Very Good, (244)
"Clean room. Good spot for family weekend getaway "
United States
ALAIN BERNARD
The price is ￥16,659
￥27,956 total
includes taxes & fees
Dec 21 - Dec 22
Sea Crest Beach Resort
Indoor pool, seasonal outdoor pool
Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

3.0 star property
East Falmouth
8.8 out of 10, Excellent, (363)
"Everything was amazing "
United States
Odetta
The price is ￥15,516
￥19,622 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Admiralty Inn & Suites - a Red Collection Hotel
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas
The Club at New Seabury

The Club at New Seabury

3.5 star property
New Seabury
9.0 out of 10, Wonderful, (338)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
United States
Jose O.
The Club at New Seabury
Indoor pool
Inn on the Square

Inn on the Square

3.5 star property
Falmouth
8.6 out of 10, Excellent, (1003)
"Great location Comfortable beds Reasonably price "
United States
Thomas
The price is ￥16,615
￥22,647 total
includes taxes & fees
Dec 15 - Dec 16
Inn on the Square
Property grounds
ShoreWay Acres Inn & Cape Cod Lodging

ShoreWay Acres Inn & Cape Cod Lodging

2.5 star property
Falmouth
8.4 out of 10, Very Good, (449)
"Very good for a lower priced motel/inn. Two minutes walk into town, so very convenient. Easy to park. "
United States
Anne Monique
The price is ￥20,814
￥23,823 total
includes taxes & fees
Dec 8 - Dec 9
ShoreWay Acres Inn & Cape Cod Lodging
Seasonal outdoor pool
Hampton Inn by Hilton New Bedford/Fairhaven

Hampton Inn by Hilton New Bedford/Fairhaven

2.5 star property
Fairhaven
8.8 out of 10, Excellent, (1003)
"Courteous staff clean room great stay "
United States
ANDREW
The price is ￥14,787
￥16,517 total
includes taxes & fees
Dec 16 - Dec 17
Hampton Inn by Hilton New Bedford/Fairhaven
Indoor pool
Falmouth Inn

Falmouth Inn

2.0 star property
Falmouth
8.0 out of 10, Very Good, (1000)
"Clean room, good shower and helpful staff."
United States
Mark
The price is ￥15,238
￥20,548 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Falmouth Inn
Indoor pool
Mansion House Inn And Spa

Mansion House Inn And Spa

3.5 star property
Vineyard Haven
9.4 out of 10, Exceptional, (1001)
"Clean, friendly staff, nice amenities, good location. Overall great stay!"
United States
Lisa
The price is ￥26,989
￥32,438 total
includes taxes & fees
Dec 8 - Dec 9
Mansion House Inn And Spa
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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Top Chilmark Hotel Reviews

Inn on the Square

Inn on the Square

10/10 Excellent
"The room was very clean and it was wonderful to have a restaurant onsite. It was only open for breakfast and lunch, but I had an excellent omlette. The staff at the Inn were professional and polite. I definitely would stay there again. The location is extremely convenient. Short walk to shops and restaurants."
Barbara 2-night trip
Posted 5 days ago
Inn on the Square

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Frequently asked questions

What are some accommodations with pools in Chilmark?
Hampton Inn by Hilton New Bedford/Fairhaven: Offers daily, a seasonal outdoor pool, and complimentary wired internet access. Falmouth Inn: Provides daily, a pool, and free self parking. Inn on the Square: Features complimentary wireless internet access, an indoor pool, and televisions. Mansion House Inn And Spa: Offers a full-service spa, an indoor pool, and a health club. Iris Hotel Cape Cod: Features a snack bar/deli, an indoor pool, and free self parking.
What is there to see and do in Chilmark?
The picturesque setting of Menemsha Beach and Lucy Vincent Beach 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.