Photo by Shobha George
Find Hotels with a Pool in Chilmark, MA
Upfront pricingOur total price for your stay includes taxes and fees
Treat yourselfSave 10% or more on over 100,000 hotels worldwide with Member Prices
Be pickySearch almost a million properties worldwide
Check availability on Chilmark Hotels with a Pool
Our top choices for Chilmark hotels with a pool
Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (21)
"We loved this property and would love to return!"
Clifford L.
$412 nightly
The price is $460
Dec 31 - Jan 1, 2026
Total with taxes and fees
Iris Hotel Cape Cod
Falmouth
8.6 out of 10, Excellent, (154)
"great bedroom "
Jessica
$105 nightly
The price is $120
Dec 11 - Dec 12
Total with taxes and fees
Sea Crest Beach Resort
North Falmouth
8.0 out of 10, Very Good, (244)
"Clean room. Good spot for family weekend getaway "
ALAIN BERNARD
$157 nightly
The price is $180
Dec 23 - Dec 24
Total with taxes and fees
Admiralty Inn & Suites - a Red Collection Hotel
East Falmouth
8.8 out of 10, Excellent, (363)
"Everything was amazing "
Odetta
$112 nightly
The price is $126
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Club at New Seabury
New Seabury
9.0 out of 10, Wonderful, (339)
"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 "
Jose O.
$136 nightly
The price is $156
Dec 28 - Dec 29
Total with taxes and fees
Inn on the Square
Falmouth
8.6 out of 10, Excellent, (1004)
"Great location
Comfortable beds
Reasonably price "
Thomas
$139 nightly
The price is $159
Dec 25 - Dec 26
Total with taxes and fees
ShoreWay Acres Inn & Cape Cod Lodging
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. "
Anne Monique
$134 nightly
The price is $153
Dec 10 - Dec 11
Total with taxes and fees
InnSeason Resorts Captain's Quarters
Falmouth Heights
9.8 out of 10, Exceptional, (192)
"Great property! Would definitely stay again."
Brad
$125 nightly
The price is $142
Dec 10 - Dec 11
Total with taxes and fees
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.
Top Chilmark Hotel Reviews
Admiralty Inn & Suites - a Red Collection Hotel
10/10 Excellent
Frequently asked questions
Explore a world of travel with Expedia
- Hotels near Chilmark Chocolates
- Pet-friendly Hotels in Menemsha
- Hotels with Restaurants in Menemsha
- Resorts & Hotels with Spas in Menemsha
- Hotels near Lucy Vincent Beach
- Menemsha Hotels
- B&B in Menemsha
- Cottages in Menemsha
- Hostels in Menemsha
- Vacation Homes in Menemsha
- Condo Resorts in Menemsha
- Hotels near Menemsha Beach
- Hotels near The Yard
- Hotels near Fulling Mill Brook Preserve
- Martha's Vineyard Hotels
- Aquinnah Hotels
- Beach Hotels in West Tisbury
- Hotels with a Pool in West Tisbury
- B&B in West Tisbury
- West Tisbury Hotels
- Vacation Homes in West Tisbury
- Hostels in West Tisbury
- Hotels near Granary Gallery
- Hotels near Grange Hall
- Hotels near Field Gallery
- Hotels near Alley’s General Store
- Hotels near Gay Head Lighthouse
- Hotels near Aquinnah Cliffs
- Oceanfront Hotels in Martha's Vineyard
- Hotels near Polly Hill Arboretum
- Cheap Hotels in Martha's Vineyard
- Pet-friendly Hotels in Martha's Vineyard
- Adults Only Resorts & in Martha's Vineyard
- Beach Hotels in Martha's Vineyard
- Luxury Hotels in Martha's Vineyard
- Romantic Hotels in Martha's Vineyard
- Family Hotels in Martha's Vineyard
- Hotels with smoking rooms in Martha's Vineyard
- Resorts & Hotels with Spas in Martha's Vineyard
- Hotels with a View in Martha's Vineyard
- Golf Hotels in Martha's Vineyard
- Hotels with a Pool in Martha's Vineyard
- Honeymoon Resorts & in Martha's Vineyard
- Historic Hotels in Martha's Vineyard
- Winery Hotels in Martha's Vineyard
- Hotel Wedding Venues Hotels in Martha's Vineyard
- Hotels with a Gym in Martha's Vineyard
- Hotels with Tennis Courts in Martha's Vineyard
- Hotels with an Indoor Pool in Martha's Vineyard
- Hotels with Free Airport Shuttle in Martha's Vineyard
- Hotels with Hot Tubs in Martha's Vineyard
- Hotels with Free Parking in Martha's Vineyard
- Hotels with Free Breakfast in Martha's Vineyard
- Hotels with Fireplaces in Martha's Vineyard
- All-inclusive Resorts in Martha's Vineyard
- Hotels with Balconies in Martha's Vineyard
- Boutique Hotels in Martha's Vineyard
- Hotels with Kitchenettes in Martha's Vineyard
- Hotels with Restaurants in Martha's Vineyard
- Hotels with Air Conditioning in Martha's Vineyard
- Hotels with Connecting Rooms in Martha's Vineyard
- Hotels with Bars in Martha's Vineyard
- Hotels with Laundry Facilities in Martha's Vineyard
- Hotels with Suites in Martha's Vineyard
- Hotels with an Outdoor Pool in Martha's Vineyard
- Hotels & Resorts for Couples in Martha's Vineyard
- Hotels with Room Service in Martha's Vineyard
- Casino Hotels in Martha's Vineyard
- Hotel with a Concierge Hotels in Martha's Vineyard
- Hotels with Childcare in Martha's Vineyard
- Business Hotels in Martha's Vineyard
- Extended Stay Hotels in Martha's Vineyard
- Gay friendly Hotels in Martha's Vineyard
- Non-Smoking Hotels in Martha's Vineyard
- Marriott Hotels & Resorts in Martha's Vineyard