Photo by Shobha George

Hotels with Pool & Resorts in Chilmark from NZ$215

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Pool

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Chilmark hotels with a pool

Outdoor pool, a heated pool
Cozy efficiency apartment/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.
Cozy efficiency apartment/heated pool
Indoor pool
Iris Hotel Cape Cod

Iris Hotel Cape Cod

Iris Hotel Cape Cod
3.0 star property
Falmouth
8.6 out of 10, Excellent, (159)
"great bedroom "
United States
Jessica
The price is NZ$215
includes taxes & fees
19 Jan - 20 Jan 2026
Iris Hotel Cape Cod
Indoor pool, seasonal outdoor pool
Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel
3.0 star property
East Falmouth
8.6 out of 10, Excellent, (370)
"Short overnight stay. Big clean rooms and comfortable beds. "
United States
Lisa
The price is NZ$218
includes taxes & fees
4 Jan - 5 Jan 2026
Admiralty Inn & Suites - a Red Collection Hotel
Indoor pool
Falmouth Inn

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 NZ$222
includes taxes & fees
4 Jan - 5 Jan 2026
Falmouth Inn
Seasonal outdoor pool, pool cabanas (surcharge), pool umbrellas
The Club at New Seabury

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (341)
"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

Inn on the Square
3.5 star property
Falmouth
8.6 out of 10, Excellent, (1002)
"Great location Comfortable beds Reasonably price "
United States
Thomas
The price is NZ$254
includes taxes & fees
14 Jan - 15 Jan 2026
Inn on the Square
Seasonal outdoor pool
InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters
3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (193)
"Best scenery ever !"
United States
Jacqueline
The price is NZ$256
includes taxes & fees
4 Jan - 5 Jan 2026
InnSeason Resorts Captain's Quarters
Property grounds
ShoreWay Acres Inn & Cape Cod Lodging

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 NZ$265
includes taxes & fees
1 Jan - 2 Jan 2026
ShoreWay Acres Inn & Cape Cod Lodging
Seasonal outdoor pool
Hampton Inn by Hilton New Bedford/Fairhaven

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, quiet"
United States
Gail
The price is NZ$223
includes taxes & fees
25 Jan - 26 Jan 2026
Hampton Inn by Hilton New Bedford/Fairhaven
Indoor pool
Mansion House Inn And Spa

Mansion House Inn And Spa

Mansion House Inn And Spa
3.5 star property
Vineyard Haven
9.4 out of 10, Exceptional, (1000)
"Our second time staying. Friendly staff, perfect location, great views. Highly recommend."
United States
Kurt
The price is NZ$361
includes taxes & fees
4 Jan - 5 Jan 2026
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.
View all properties

Top Chilmark Hotel Reviews

Inn on the Square

Inn on the Square

10/10 Excellent
"This was our 2nd stay. We stay here when visiting family in December. Hotel is clean, comfortable and quiet. Bathroom is spacious. Very easy to walk town. "
Karen 2-night trip
Posted 5 days ago
Inn on the Square

Frequently asked questions

What are some accommodation options with pools in Chilmark?
Iris Hotel Cape Cod: Offers a snack bar/deli, an indoor pool and free self parking. Faraway Martha's Vineyard: Provides 2 restaurants, a seasonal outdoor pool and complimentary high-speed (wired) Internet access. Falmouth Inn: Features daily, a pool and free self parking. Harbor View Hotel: Offers free self parking, a seasonal outdoor pool and complimentary bicycles. Hampton Inn by Hilton New Bedford/Fairhaven: Features daily, a seasonal outdoor pool and complimentary high-speed (wired) Internet access.
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, visit 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 the local weather in Chilmark into account can help you maximise your time at the pool during your trip. The hottest months are usually August and July, with an average temperature of 20°C, while the coldest months are February and January, with an average of 3°C. Average annual precipitation for Chilmark is 1272 mm.