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

Hotels with Swimming Pool in Chilmark, Massachusetts

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Check availability on Chilmark Hotels with Swimming Pool

Tonight
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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 balcony with a table and chairs, overlooking a marina with boats and a distant shoreline.
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.

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.
P10,868
P13,063 total
includes taxes & fees
Nov 2 - Nov 3
Mansion House Inn And Spa
A swimming pool with blue lounge chairs and a stone building in the background.
A restaurant with wooden flooring, high ceilings, and large windows. Tables are set with chairs and centerpieces.
A room with a wooden deck, a white dresser, and a window with a view of a yard.
A covered porch with wicker furniture and a vase of flowers.

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.
P15,144
P16,916 total
includes taxes & fees
Nov 1 - Nov 2
Lamberts Cove Inn
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 deck with a wicker sofa, a table with a bottle of champagne, and a tray of snacks.

3. Harbor View Hotel

Harbor View Hotel
Edgartown
  • Seasonal harbor-side pool escape offers refreshing coastal views and luxury poolside cocktail service.
P15,247
P18,393 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 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.

4. 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.
P14,637
P17,167 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.
Outdoor seating with tables and chairs, covered by green umbrellas, and a sign for a breakfast and lunch place.
A large, two-story building with a stone facade, a prominent sign reading "Inn on the Square," and a patio area with outdoor seating.

5. 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.
P7,760
P10,456 total
includes taxes & fees
Nov 1 - Nov 2
Inn on the Square
A poolside area with lounge chairs and a table.
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 dining area with multiple tables and chairs, a kitchen area with appliances, and a television displaying a logo.
A gym with treadmills, a bench, and a mirrored wall.

6. 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.
P6,755
P8,482 total
includes taxes & fees
Nov 1 - Nov 2
Admiralty Inn & Suites - a Red Collection Hotel
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 long dining table with a glass centerpiece, surrounded by chairs and a buffet setup.
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.
P8,069
P9,235 total
includes taxes & fees
Nov 1 - Nov 2
Iris Hotel Cape Cod
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 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.

8. 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.
P6,859
P7,661 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn by Hilton New Bedford/Fairhaven
An indoor swimming pool with lounge chairs, a lifeguard sign, and American flags.
A bar area with multiple screens displaying sports content, a counter with various bottles, and a seating area with tables and chairs.
A modern hotel room with a curved ceiling, a large bed, a flat-screen TV, a desk with a chair, and a bathroom with a mirror and sink.
An aerial view of a marina with boats, a pier, and a town with houses and buildings.

9. Falmouth Inn

Falmouth Inn
Falmouth
  • Dive into refreshing comfort with an indoor pool oasis that's perfect year-round at this Cape Cod getaway with beach access.
P8,069
P10,486 total
includes taxes & fees
Oct 12 - Oct 13
Falmouth Inn
A bathroom with a white sink, a toilet, a shower with a glass-enclosed tub, a round mirror, and a shelf with toiletries.
A building with a sign reading "Mariner Motel" and a garden with various flowers in front.
A fenced backyard with a pool, picnic table, and trees.
A Mariner Motel sign with a vacancy notice, surrounded by vibrant flowers.

10. Mariner Motel

Mariner Motel
Falmouth
  • Dive into seaside serenity at this coastal retreat with a sun-drenched pool oasis.
P8,069
P9,235 total
includes taxes & fees
Oct 7 - Oct 8
Mariner Motel
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

Falmouth Inn

Falmouth Inn

8/10 Good
"The Inn served our needs great location rooms were clean and had all of our needs"
Larry 1-night trip
Posted 2 hours ago
Falmouth Inn
Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent
"Honestly, I was pleasantly surprised by how nice and clean it was, and how safe I felt at the property. I read some of the previous reviews and was a little nervous but upon arrival, I was completely at ease. The room was very spacious, updated, clean, and everything was in working order. It had a nicer than usual coffee hot and ion blow dryer. Those are some nice touches. Breakfast was wonderful as well."
sherry 1-night trip
Posted 1 day 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 7 days ago
Hampton Inn by Hilton New Bedford/Fairhaven

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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