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

Find Hotels with a Pool in Chilmark, MA

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Check availability on Chilmark Hotels with a Pool

Tonight
Oct 4 - Oct 5
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Oct 5 - Oct 6
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Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Chilmark hotels with a pool

A two-story house with a swimming pool, a covered patio, and a fenced backyard.
A bedroom with a bed, a bedside table, a lamp, a picture on the wall, and a window with curtains.
A backyard with a barbecue grill, a table, and chairs. There is a wooden fence, a window, and some greenery.
A small kitchen with a wooden table, chairs, a microwave, a toaster, and a refrigerator.

1. Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
$537 nightly
$600 total
Oct 13 - Oct 14
Total with taxes and fees
Cozy efficiency apartment/heated pool
A swimming pool with blue lounge chairs and a stone building in the background.
A covered porch with wicker furniture and a vase of flowers.
A room with a wooden deck, a white dresser, and a window with a view of a yard.
A cozy room with a grey sofa, a wooden bench, and a tray with a plant.

2. Lamberts Cove Inn

Lamberts Cove Inn
Vineyard Haven
  • Escape to a private beachside haven with a seasonal pool, where comfort meets coastal charm and nature's serenity awaits you.
$242 nightly
$270 total
Nov 1 - Nov 2
Total with taxes and fees
Lamberts Cove Inn
An indoor swimming pool with clear lane markings, tiled walls, and a ceiling with recessed lighting.
A balcony with a table and chairs, overlooking a marina with boats and a distant shoreline.
A spacious living room with a large sofa, a chair, and a small table. There are several potted plants and a ceiling fan.
A marina with boats docked along the shore, surrounded by greenery and a sandy beach.

3. Mansion House Inn And Spa

Mansion House Inn And Spa
Vineyard Haven
  • Refreshing indoor pool sanctuary complements rooftop terrace views and a soothing hot tub at this Martha's Vineyard spa retreat.
$187 nightly
$209 total
Nov 2 - Nov 3
Total with taxes and fees
Mansion House Inn And Spa
A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.
Outdoor seating with tables and chairs, covered by green umbrellas, and a sign for a breakfast and lunch place.
A hotel room with a large bed, a sitting area with a chair and a table, a bathtub, and a framed picture on the wall.
A staircase with wooden railings and a lamp on a side table.

4. Inn on the Square

Inn on the Square
Falmouth
  • Sun-drenched days await at the indoor pool retreat where year-round swimming creates vacation bliss.
$121 nightly
$139 total
Nov 2 - Nov 3
Total with taxes and fees
Inn on the Square
A poolside area with lounge chairs, a wooden deck, and a pool.
A spacious dining area with a long table surrounded by wicker chairs, wooden panel walls, and large windows.
A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.
A spacious lobby with a reception desk, a large sofa, and a chandelier.

5. Faraway Martha's Vineyard

Faraway Martha's Vineyard
Edgartown
  • Dive into poolside bliss with comfy loungers, a hot tub, and a convenient bar for refreshments.
$246 nightly
$274 total
Nov 1 - Nov 2
Total with taxes and fees
Faraway Martha's Vineyard
An indoor swimming pool with clear blue water, surrounded by blue lounge chairs and a tiled floor.
A beach with people sunbathing and swimming, a clear blue sky, and a sailboat in the distance.
A long dining table with a glass centerpiece, surrounded by chairs and a buffet setup.
A cozy living room with a stone fireplace, leather sofas, and a large window with blinds.

6. Iris Hotel Cape Cod

Iris Hotel Cape Cod
Falmouth
  • Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
$129 nightly
$148 total
Nov 1 - Nov 2
Total with taxes and fees
Iris Hotel Cape Cod
A large, multi-story house with a covered porch and a well-maintained lawn.
A modern living room with a wicker chair, a round coffee table with a vase, and a sofa with patterned cushions.
A modern bathroom with a wooden vanity, a round mirror, and a glass shower enclosure.
A neatly arranged bedroom with a bed, pillows, a vase, and a lamp.

7. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
$162 nightly
$190 total
Oct 13 - Oct 14
Total with taxes and fees
Shore Haven Inn
A poolside area with lounge chairs and a table.
A hotel room with a large bed, a sofa, a desk, a TV, and a painting on the wall.
A room with two beige armchairs, a patterned carpet, a large window with a view of buildings, and a ceiling with recessed lighting and a smoke detector.
A gym with treadmills, a bench, and a mirrored wall.

8. Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel
East Falmouth
  • Dive into year-round aquatic bliss with indoor and seasonal outdoor pools in Cape Cod.
$120 nightly
$136 total
Nov 1 - Nov 2
Total with taxes and fees
Admiralty Inn & Suites - a Red Collection Hotel
A swimming pool with lounge chairs and umbrellas, surrounded by a building with a balcony and a clear sky.
A resort with a swimming pool, outdoor seating, and a view of the lake.
A deck with a wicker sofa, a table with a bottle of champagne, and a tray of snacks.
A balcony with a view of the harbor, a dining area with a table and chairs, and a small seating area with a bench and a table.

9. Harbor View Hotel

Harbor View Hotel
Edgartown
  • Seasonal harbor-side pool escape offers refreshing coastal views and luxury poolside cocktail service.
$263 nightly
$294 total
Oct 25 - Oct 26
Total with taxes and fees
Harbor View Hotel
An aerial view of a resort with a pool, beach area with umbrellas, and a large building with a covered deck.
A restaurant with tables set for dining, overlooking a beach.
A beachside seating area with blue umbrellas and lounge chairs.
A golf course with a clubhouse, a lake, and surrounding trees.

10. The Club at New Seabury

The Club at New Seabury
New Seabury
  • Splash into poolside bliss at this Cape Cod resort with cabanas, loungers, and two vibrant bars.
$147 nightly
$169 total
Nov 1 - Nov 2
Total with taxes and fees
The Club at New Seabury
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Choose what matters most at hotels with a pool in Chilmark

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Chilmark Hotel Reviews

Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

8/10 Good
"We stayed in the two bedroom suite. Room and bathroom were very clean and spacious. It did have a spiral staircase, which was ill situated. We had to hang towels off the stairs so nobody would bump their head. Continental Breakfast was delicious. We stayed in October. Would love to go back there in the summer."
Lynne 1-night trip
Posted 20 hours ago
Admiralty Inn & Suites - a Red Collection Hotel
Hampton Inn by Hilton New Bedford/Fairhaven

Hampton Inn by Hilton New Bedford/Fairhaven

8/10 Good
"Delicious egg frittatas!"
Caroline 2-night trip
Posted 5 days ago
Hampton Inn by Hilton New Bedford/Fairhaven

Frequently asked questions

What are some accommodations with pools in Chilmark?
Cozy efficiency apartment/heated pool: Features complimentary wireless internet access, a pool, and Smart TVs. Sea Crest Beach Resort: Hotel, 2-minute walk from Cape Cod Beaches. Offers a children's pool, a seasonal outdoor pool, and a private beach. Iris Hotel Cape Cod: Provides a snack bar/deli, an indoor pool, and free self parking. Inn on the Square: Features complimentary wireless internet access, an indoor pool, and televisions. Summercamp: 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, 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.

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