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

Chilmark Hotel Guide - Hotels with Pool in Chilmark, Massachusetts

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Check availability on Chilmark Hotels with Pool

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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 bedroom with a bed, a bedside table, a lamp, a picture on the wall, and a window with curtains.
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
€536
includes taxes & fees
13 Oct - 14 Oct
Cozy efficiency apartment/heated 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 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.

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.
€241
includes taxes & fees
1 Nov - 2 Nov
Lamberts Cove Inn
An indoor swimming pool with clear lane markings, tiled walls, and a ceiling with recessed lighting.
A marina with boats docked along the shore, surrounded by greenery and a sandy beach.
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.

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.
€186
includes taxes & fees
2 Nov - 3 Nov
Mansion House Inn And Spa
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.
An outdoor patio with a bar area, seating, and string lights.

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.
€245
includes taxes & fees
1 Nov - 2 Nov
Faraway Martha's Vineyard
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 spacious living area with a dining table, sofas, and a view of the sea.

5. Harbor View Hotel

Harbor View Hotel
Edgartown
  • Seasonal harbor-side pool escape offers refreshing coastal views and luxury poolside cocktail service.
€262
includes taxes & fees
25 Oct - 26 Oct
Harbor View Hotel
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 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.

6. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
€185
includes taxes & fees
13 Oct - 14 Oct
Shore Haven Inn
An aerial view of a resort with a pool, beach area with umbrellas, and a large building with a covered deck.
A beachside seating area with blue umbrellas and lounge chairs.
A golf course with a clubhouse, a lake, and surrounding trees.
A restaurant with tables set for dining, overlooking a beach.

7. 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.
€150
includes taxes & fees
1 Nov - 2 Nov
The Club at New Seabury
A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.
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.
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.

8. 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.
€167
includes taxes & fees
12 Oct - 13 Oct
Inn on the Square
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 beach with people sunbathing and swimming, a clear blue sky, and a sailboat in the distance.
A cozy living room with a stone fireplace, leather sofas, and a large window with blinds.

9. Iris Hotel Cape Cod

Iris Hotel Cape Cod
Falmouth
  • Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
€132
includes taxes & fees
1 Nov - 2 Nov
Iris Hotel Cape Cod
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 dining area with multiple tables and chairs, a kitchen area with appliances, and a television displaying a logo.
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.

10. 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.
€121
includes taxes & fees
1 Nov - 2 Nov
Admiralty Inn & Suites - a Red Collection Hotel
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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

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 16 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 8 days ago
Hampton Inn by Hilton New Bedford/Fairhaven

Frequently asked questions

What are some accommodation options with pools in Chilmark?
Cozy efficiency apartment/heated pool: Features complimentary wireless Internet access, a pool and Smart televisions. 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, 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 20°C, while the coldest months are February and January, with an average of 3°C. Average annual precipitation for Chilmark is 1272 mm.