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

Find Hotels with a Pool in Chilmark, MA

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Check availability on Chilmark Hotels with a Pool

Tonight
Oct 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 marina with boats docked along the shore, surrounded by greenery and a sandy beach.
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.
$187 nightly
$209 total
Nov 2 - Nov 3
Total with taxes and fees
Mansion House Inn And Spa
A large, multi-story house with a covered porch and a well-maintained lawn.
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.
A hotel room with two beds, a large window, a flat-screen TV, and a painting on the wall.

2. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
$167 nightly
$196 total
Nov 12 - Nov 13
Total with taxes and fees
Shore Haven Inn
A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.
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.
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.

3. 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.
$142 nightly
$163 total
Nov 12 - Nov 13
Total with taxes and fees
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 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.

4. Iris Hotel Cape Cod

Iris Hotel Cape Cod
Falmouth
  • Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
$129 nightly
$148 total
Nov 15 - Nov 16
Total with taxes and fees
Iris Hotel Cape Cod
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.
An outdoor patio with a bar area, seating, and string lights.

5. 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.
$246 nightly
$274 total
Nov 4 - Nov 5
Total with taxes and fees
Faraway Martha's Vineyard
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.

6. 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.
$419 nightly
$468 total
Oct 30 - Oct 31
Total with taxes and fees
Lamberts Cove Inn
A swimming pool with lounge chairs and a view of the ocean.
A dining area with tables and chairs, large windows with a view of the sea, and ceiling fans.
A beach with rows of sun loungers and umbrellas, a building with a glass facade, and a forested hill in the background.
A hotel with a well-maintained garden, a central fire feature, and a sign reading "Sea Crest".

7. Sea Crest Beach Resort

Sea Crest Beach Resort
North Falmouth
  • Dive into pure coastal bliss with three pools and beach access at this oceanfront hotel.
$169 nightly
$193 total
Nov 4 - Nov 5
Total with taxes and fees
Sea Crest Beach Resort
A poolside area with lounge chairs and a table.
A hotel room with a bed, a desk, a TV, and a mirror.
A dining area with multiple tables and chairs, a kitchen area with appliances, and a television displaying a logo.
A lobby with a black sofa, two armchairs, a coffee table, a potted plant, and a display cabinet with decorative items.

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.
$132 nightly
$149 total
Nov 1 - Nov 2
Total with taxes and fees
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 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 spacious living area with a dining table, sofas, and a view of the sea.

9. Harbor View Hotel

Harbor View Hotel
Edgartown
  • Seasonal harbor-side pool escape offers refreshing coastal views and luxury poolside cocktail service.
$316 nightly
$353 total
Nov 4 - Nov 5
Total with taxes and fees
Harbor View Hotel
An aerial view of a resort with a pool, beach area with umbrellas, and a large building with a covered deck.
A golf course with a clubhouse, a lake, and surrounding trees.
A restaurant with tables set for dining, overlooking a beach.
A row of white lounge chairs with blue cushions, arranged under a white canopy, overlooking the sea.

10. 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.
$173 nightly
$198 total
Nov 4 - Nov 5
Total with taxes and fees
The Club at New Seabury
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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
"OK as expected"
Boris G 2-night trip
Posted 5 hours ago
Falmouth Inn
Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent
"Great cheap place to stay. Breakfast was good"
Maryrose 2-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

10/10 Excellent
"Clean matters to me !"
Setsuo 1-night trip
Posted 4 days ago
Hampton Inn by Hilton New Bedford/Fairhaven
Faraway Martha's Vineyard

Faraway Martha's Vineyard

10/10 Excellent
"My stay was wonderful. The well-maintained and beautiful hotel had the best staff I’ve ever experienced!"
Krystin 2-night trip
Posted 6 days ago
Faraway Martha's Vineyard

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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