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

Chilmark Hotels with Swimming Pool

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Check availability on Chilmark Hotels with Swimming Pools

Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Chilmark hotels with a pool

A swimming pool with blue lounge chairs and a stone building in the background.
A cozy room with a grey sofa, a wooden bench, and a tray with a plant.
A restaurant with wooden flooring, high ceilings, and large windows. Tables are set with chairs and centerpieces.
A covered porch with wicker furniture and a vase of flowers.

1. 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.
RM1,246
RM1,392 total
includes taxes & fees
13 Oct - 14 Oct
Lamberts Cove Inn
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 balcony with a table and chairs, overlooking a marina with boats and a distant shoreline.
A marina with boats docked along the shore, surrounded by greenery and a sandy beach.

2. 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.
RM710
RM853 total
includes taxes & fees
2 Nov - 3 Nov
Mansion House Inn And Spa
A poolside area with lounge chairs, a wooden deck, and a pool.
An outdoor patio with a bar area, seating, and string lights.
A spacious lobby with a reception desk, a large sofa, and a chandelier.
A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.

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.
RM956
RM1,121 total
includes taxes & fees
1 Nov - 2 Nov
Faraway Martha's Vineyard
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.

4. The Harborside Inn

The Harborside Inn
Edgartown
  • Float in blissful style at a seasonal outdoor pool, where relaxation meets Martha's Vineyard magic.
RM1,945
RM2,172 total
includes taxes & fees
7 Nov - 8 Nov
The Harborside Inn
A pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows.
A hotel room with a large bed, a desk, a chair, a TV, and a window with a view.
A hotel dining area with multiple tables and chairs, a bar, and a seating area with a patterned wall.
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.

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.
RM448
RM500 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn by Hilton New Bedford/Fairhaven
An indoor swimming pool with clear blue water, surrounded by blue lounge chairs and a tiled floor.
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.
A reception desk with a floral arrangement in a green vase, a marble wall with "HOTEL CAP" signage, and a white counter.

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.
RM527
RM603 total
includes taxes & fees
1 Nov - 2 Nov
Iris Hotel Cape Cod
A poolside area with lounge chairs and a table.
A covered outdoor area with a pool, red chairs, and a table.
A hotel room with two beds, a desk, and a chair.
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.

7. 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.
RM460
RM575 total
includes taxes & fees
1 Nov - 2 Nov
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 spacious living area with a dining table, sofas, and a view of the sea.
A resort with a swimming pool, outdoor seating, and a view of the lake.
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.

8. Harbor View Hotel

Harbor View Hotel
Edgartown
  • Seasonal harbor-side pool escape offers refreshing coastal views and luxury poolside cocktail service.
RM1,195
RM1,442 total
includes taxes & fees
25 Oct - 26 Oct
Harbor View Hotel
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 staircase with wooden railings and a lamp on a side table.
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.

9. Inn on the Square

Inn on the Square
Falmouth
  • Sun-drenched days await at the indoor pool retreat where year-round swimming creates holiday bliss.
RM614
RM805 total
includes taxes & fees
13 Oct - 14 Oct
Inn on the Square
A large, multi-story house with a covered porch and a well-maintained lawn.
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.
A modern living room with a wicker chair, a round coffee table with a vase, and a sofa with patterned cushions.

10. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
RM724
RM851 total
includes taxes & fees
13 Oct - 14 Oct
Shore Haven Inn
View all properties

Choose what matters most at hotels with a pool in Chilmark

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Chilmark Hotel Reviews

Sea Crest Beach Resort

Sea Crest Beach Resort

8/10 Good
"We went for a September wedding and stayed one night. Perfect access to the beach and a short drive to town. Staff were amazing! Mostly updated but a few thing - doors especially- still need an upgrade."
Heather 1-night trip
Posted 1 day ago
Sea Crest Beach Resort
Inn on the Square

Inn on the Square

10/10 Excellent
"Very comfortable bed!"
Tyler 1-night trip
Posted 2 days ago
Inn on the Square
Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"It was a perfect location for us, it was clean, updated and we slept great!"
Jennie 1-night trip
Posted 2 days 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 2 days ago
Harbor View Hotel

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 20Β°C, while the coldest months are February and January, with an average of 3Β°C. Average annual precipitation for Chilmark is 1272 mm.

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