Search Hotels with Pool in Chilmark

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Check prices for these dates

Tonight
6 Nov - 7 Nov
Tomorrow
7 Nov - 8 Nov
This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Chilmark hotels with a pool

A pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows.

1. Hampton Inn by Hilton New Bedford/Fairhaven

Hampton Inn by Hilton New Bedford/Fairhaven
2.5 star property
Fairhaven
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Seasonal outdoor pool beckons with refreshing waters, offering a perfect retreat from warm summer days in New Bedford.
The price is ฿3,101
฿3,463 total
includes taxes & fees
3 Dec - 4 Dec
Hampton Inn by Hilton New Bedford/Fairhaven
A swimming pool with blue lounge chairs and a stone building in the background.

2. Lamberts Cove Inn

Lamberts Cove Inn
3.5 star property
Vineyard Haven
9.4 out of 10, Exceptional, (90 reviews)
  • cleanliness
    Escape to a private beachside haven with a seasonal pool, where comfort meets coastal charm and nature's serenity awaits you.
The price is ฿11,159
฿12,465 total
includes taxes & fees
25 Nov - 26 Nov
Lamberts Cove Inn
An indoor swimming pool with clear lane markings, tiled walls, and a ceiling with recessed lighting.

3. Mansion House Inn And Spa

Mansion House Inn And Spa
3.5 star property
Vineyard Haven
9.4 out of 10, Exceptional, (1,001 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary complements rooftop terrace views and a soothing hot tub at this Martha's Vineyard spa retreat.
The price is ฿5,815
฿6,988 total
includes taxes & fees
8 Nov - 9 Nov
Mansion House Inn And Spa
A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.

4. Inn on the Square

Inn on the Square
3.5 star property
Falmouth
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Sun-drenched days await at the indoor pool retreat where year-round swimming creates holiday bliss.
The price is ฿4,712
฿6,235 total
includes taxes & fees
22 Nov - 23 Nov
Inn on the Square
A poolside area with lounge chairs and a table.

5. 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, (576 reviews)
  • cleanliness
    Dive into year-round aquatic bliss with indoor and seasonal outdoor pools in Cape Cod.
The price is ฿4,005
฿4,986 total
includes taxes & fees
11 Nov - 12 Nov
Admiralty Inn & Suites - a Red Collection Hotel
A poolside area with lounge chairs, a wooden deck, and a pool.

6. Faraway Martha's Vineyard

Faraway Martha's Vineyard
4.0 star property
Edgartown
9.0 out of 10, Wonderful, (1,007 reviews)
  • cleanliness
    Dive into poolside bliss with comfy loungers, a hot tub, and a convenient bar for refreshments.
The price is ฿7,530
฿8,831 total
includes taxes & fees
6 Dec - 7 Dec
Faraway Martha's Vineyard
An indoor swimming pool with clear blue water, surrounded by blue lounge chairs and a tiled floor.

7. Iris Hotel Cape Cod

Iris Hotel Cape Cod
3.0 star property
Falmouth
8.4 out of 10, Very good, (439 reviews)
  • cleanliness
    Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
The price is ฿3,982
฿4,557 total
includes taxes & fees
17 Nov - 18 Nov
Iris Hotel Cape Cod
A waterfront hotel with a pool, outdoor seating, and a view of the water.

8. The Harborside Inn

The Harborside Inn
3.5 star property
Edgartown
9.0 out of 10, Wonderful, (441 reviews)
  • cleanliness
    Float in blissful style at a seasonal outdoor pool, where relaxation meets Martha's Vineyard magic.
The price is ฿15,929
฿17,793 total
includes taxes & fees
7 Nov - 8 Nov
The Harborside Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a building with a balcony and a clear sky.

9. Harbor View Hotel

Harbor View Hotel
5.0 star property
Edgartown
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Seasonal harbor-side pool escape offers refreshing coastal views and luxury poolside cocktail service.
The price is ฿9,789
฿11,809 total
includes taxes & fees
15 Nov - 16 Nov
Harbor View Hotel
An indoor swimming pool with lounge chairs, a lifeguard sign, and American flags.

10. Falmouth Inn

Falmouth Inn
2.0 star property
Falmouth
8.0 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Dive into refreshing comfort with an indoor pool oasis that's perfect year-round at this Cape Cod getaway with beach access.
The price is ฿3,982
฿5,227 total
includes taxes & fees
11 Nov - 12 Nov
Falmouth Inn
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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Choose what matters most at hotels with a pool in Chilmark

Breakfast included
4 stars

Top Chilmark Hotel Reviews

A swimming pool with blue lounge chairs and a stone building in the background.
Lamberts Cove Inn

Lamberts Cove Inn

Lamberts Cove Inn
Vineyard Haven

10/10 Excellent

Amazing stay at the property with great hosts
United Kingdom
Shyam
Reviewed April 21, 2025
Lamberts Cove Inn

Frequently Asked Questions

What are some accommodation options with pools in Chilmark?

Sea Crest Beach Resort: Features complimentary wireless Internet access, a pool and Smart televisions. Iris Hotel Cape Cod : Hotel, 2-minute walk from Cape Cod Beaches. Offers a children's pool, a seasonal outdoor pool and a private beach. Inn on the Square: Provides a snack bar/deli, an indoor pool and free self parking. Summercamp: Features complimentary wireless Internet access, an indoor pool and televisions. Falmouth Inn: Features daily, a pool and free self parking.

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.