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

Find Hotels with a Pool in Chilmark, MA from CA $193

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Check availability on Chilmark Hotels with a Pool

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
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 bathroom with a toilet, a shower curtain, and a toilet paper holder.
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
CA $563
CA $855 total
includes taxes & fees
Oct 13 - Oct 14
Cozy efficiency apartment/heated pool
A swimming pool with blue lounge chairs and a stone building in the background.
A room with a wooden deck, a white dresser, and a window with a view of a yard.
A restaurant with wooden flooring, high ceilings, and large windows. Tables are set with chairs and centerpieces.
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.
CA $345
CA $385 total
includes taxes & fees
Nov 1 - Nov 2
Lamberts Cove Inn
An indoor swimming pool with clear lane markings, tiled walls, and a ceiling with recessed lighting.
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.
A balcony with a table and chairs, overlooking a marina with boats and a distant shoreline.

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.
CA $248
CA $298 total
includes taxes & fees
Nov 3 - Nov 4
Mansion House Inn And Spa
A poolside area with lounge chairs, a wooden deck, and a pool.
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.
A spacious dining area with a long table surrounded by wicker chairs, wooden panel walls, and large windows.

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.
CA $333
CA $391 total
includes taxes & fees
Nov 5 - Nov 6
Faraway Martha's Vineyard
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 reception desk with a floral arrangement in a green vase, a marble wall with "HOTEL CAP" signage, and a white counter.

5. Iris Hotel Cape Cod

Iris Hotel Cape Cod
Falmouth
  • Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
CA $184
CA $210 total
includes taxes & fees
Nov 1 - Nov 2
Iris Hotel Cape Cod
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 staircase with wooden railings and a lamp on a side table.
Outdoor seating with tables and chairs, covered by green umbrellas, and a sign for a breakfast and lunch place.

6. 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.
CA $147
CA $204 total
includes taxes & fees
Nov 2 - Nov 3
Inn on the Square
A poolside area with lounge chairs and a table.
A gym with treadmills, a bench, and a mirrored 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 dining area with multiple tables and chairs, a kitchen area with appliances, and a television displaying a logo.

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.
CA $154
CA $193 total
includes taxes & fees
Nov 1 - Nov 2
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 deck with a wicker sofa, a table with a bottle of champagne, and a tray of snacks.
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.

8. Harbor View Hotel

Harbor View Hotel
Edgartown
  • Seasonal harbor-side pool escape offers refreshing coastal views and luxury poolside cocktail service.
CA $347
CA $419 total
includes taxes & fees
Oct 25 - Oct 26
Harbor View Hotel
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 hotel room with two beds, a large window, a flat-screen TV, and a painting on the wall.
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.
CA $232
CA $273 total
includes taxes & fees
Oct 13 - Oct 14
Shore Haven Inn
A pool area with lounge chairs and umbrellas, surrounded by a building with multiple windows.
A hotel dining area with multiple tables and chairs, a bar, and a seating area with a patterned wall.
A hotel room with a large bed, a desk, a chair, a TV, and a window with a view.
A gym with treadmills, weight machines, and exercise balls.

10. 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.
CA $156
CA $175 total
includes taxes & fees
Nov 2 - Nov 3
Hampton Inn by Hilton New Bedford/Fairhaven
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 8 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 2 days 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?
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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