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

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Check availability on Chilmark Hotels with a Pool

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Chilmark hotels with a pool

An indoor swimming pool with clear lane markings, tiled walls, and a ceiling with recessed lighting.
A large, multi-story building with a balcony on the second floor.
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.

1. 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.
₩233,477
₩280,615 total
includes taxes & fees
Nov 2 - Nov 3
Mansion House Inn And Spa
A swimming pool with lounge chairs and umbrellas, surrounded by a building with a balcony and a clear sky.
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.
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.

2. Harbor View Hotel

Harbor View Hotel
Edgartown
  • Seasonal harbor-side pool escape offers refreshing coastal views and luxury poolside cocktail service.
₩393,047
₩474,173 total
includes taxes & fees
Oct 25 - Oct 26
Harbor View Hotel
A poolside area with lounge chairs, a wooden deck, and a pool.
An outdoor patio with a bar area, seating, and string lights.
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.

3. 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.
₩312,343
₩366,333 total
includes taxes & fees
Nov 1 - Nov 2
Faraway Martha's Vineyard
A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.
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 large, two-story building with a stone facade, a prominent sign reading "Inn on the Square," and a patio area with outdoor seating.
Outdoor seating with tables and chairs, covered by green umbrellas, and a sign for a breakfast and lunch place.

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.
₩200,561
₩263,152 total
includes taxes & fees
Oct 25 - Oct 26
Inn on the Square
A pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows.
A compact hotel room with a kitchenette, a dining area with a yellow chair, a gray sofa with a red pillow, and a large mirror above the sink.
A gym with treadmills, weight machines, and exercise balls.
A hotel room with a large bed, a desk, a chair, a TV, and a window with a view.

5. Hampton Inn by Hilton New Bedford/Fairhaven

Hampton Inn by Hilton New Bedford/Fairhaven
Fairhaven
  • Seasonal outdoor pool beckons with refreshing waters, offering a perfect retreat from warm summer days in New Bedford.
₩147,342
₩164,581 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn by Hilton New Bedford/Fairhaven
A waterfront hotel with a pool, outdoor seating, and a view of the water.
A sandy beach path leading to the ocean, surrounded by sparse vegetation.
A spacious room with a dark blue sofa, white walls, and large windows offering a view of a building and a grassy area.
A view from a window overlooking a dock with a boat, a pier, and a building with a blue roof.

6. The Harborside Inn

The Harborside Inn
Edgartown
  • Float in blissful style at a seasonal outdoor pool, where relaxation meets Martha's Vineyard magic.
₩639,625
₩714,458 total
includes taxes & fees
Nov 7 - Nov 8
The Harborside Inn
An indoor swimming pool with clear blue water, surrounded by blue lounge chairs and a tiled floor.
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.
A beach with people sunbathing and swimming, a clear blue sky, and a sailboat in the distance.

7. Iris Hotel Cape Cod

Iris Hotel Cape Cod
Falmouth
  • Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
₩172,184
₩197,065 total
includes taxes & fees
Nov 1 - Nov 2
Iris Hotel Cape Cod
A poolside area with lounge chairs and a table.
A dining area with multiple tables and chairs, a kitchen area with appliances, and a television displaying a logo.
A covered outdoor area with a pool, red chairs, and a table.
A hotel room with two beds, a desk, and a chair.

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.
₩150,153
₩187,868 total
includes taxes & fees
Nov 11 - Nov 12
Admiralty Inn & Suites - a Red Collection Hotel
A large, multi-story house with a covered porch and a well-maintained lawn.
A hotel room with two beds, a large window, a flat-screen TV, and a painting on the wall.
A modern living room with a wicker chair, a round coffee table with a vase, and a sofa with patterned cushions.
A neatly arranged bedroom with a bed, pillows, a vase, and a lamp.

9. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
₩238,259
₩279,837 total
includes taxes & fees
Oct 19 - Oct 20
Shore Haven Inn
A swimming pool with a white fence, lounge chairs, and a view of a building in the background.
A room with a round glass table, two wicker chairs, a vase of flowers, and a view of a harbor with boats and buildings.
A two-story house with a white fence in front.
A large house with a dock and several boats on a lake surrounded by dense greenery.

10. Sands of Time Motor Inn & Harbor House

Sands of Time Motor Inn & Harbor House
Woods Hole
  • Heated pool oasis with loungers nestled in beautiful gardens at Woods Hole hotel.
₩308,995
₩353,648 total
includes taxes & fees
Oct 19 - Oct 20
Sands of Time Motor Inn & Harbor House
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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

Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"Nice stay."
Erin 1-night trip
Posted 19 hours ago
Iris Hotel Cape Cod
Harbor View Hotel

Harbor View Hotel

10/10 Excellent
"Beautiful Hotel and Venue with impeccable amenities. Beautiful water views and outstanding and friendly Staff. Disappointed we were not able to stay longer. Will definitely plan another trip in the near future!"
Marc 1-night trip
Posted 5 days ago
Harbor View Hotel

Frequently asked questions

What are some accommodations with pools in Chilmark?
Sea Crest Beach Resort: Features complimentary wireless internet access, a pool, and Smart TVs. 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, 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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