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

Find Hotels with a Pool in Chilmark, MA

Check availability on Chilmark Hotels with a Pool

Tonight
Aug 10 - Aug 11
Tomorrow
Aug 11 - Aug 12
This weekend
Aug 14 - Aug 16
Next weekend
Aug 21 - Aug 23

Our top choices for Chilmark hotels with a pool

1. 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.
$142 nightly
$160 total
Sep 7 - Sep 8
Total with taxes and fees
Falmouth Inn

2. 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.
$131 nightly
$146 total
Aug 31 - Sep 1
Total with taxes and fees
Hampton Inn by Hilton New Bedford/Fairhaven

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.
$213 nightly
$243 total
Sep 3 - Sep 4
Total with taxes and fees
Inn on the Square

4. 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.
$143 nightly
$162 total
Aug 31 - Sep 1
Total with taxes and fees
Admiralty Inn & Suites - a Red Collection Hotel

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.
$136 nightly
$156 total
Sep 7 - Sep 8
Total with taxes and fees
Iris Hotel Cape Cod

6. Mariner Motel

Mariner Motel
Falmouth
  • Dive into seaside serenity at this coastal retreat with a sun-drenched pool oasis.
$139 nightly
$159 total
Aug 30 - Aug 31
Total with taxes and fees
Mariner Motel

7. 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.
$387 nightly
$432 total
Sep 7 - Sep 8
Total with taxes and fees
Mansion House Inn And Spa

8. ShoreWay Acres Inn & Cape Cod Lodging

ShoreWay Acres Inn & Cape Cod Lodging
Falmouth
  • Splash into a refreshing escape at this inn with both indoor and seasonal outdoor pools just steps from the beach.
$199 nightly
$228 total
Aug 31 - Sep 1
Total with taxes and fees
ShoreWay Acres Inn & Cape Cod Lodging

9. Sands of Time Motor Inn & Harbor House

Sands of Time Motor Inn & Harbor House
Woods Hole
  • Heated pool oasis with loungers nestled in beautiful gardens at Woods Hole hotel.
$272 nightly
$311 total
Sep 1 - Sep 2
Total with taxes and fees
Sands of Time Motor Inn & Harbor House

10. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
$226 nightly
$265 total
Sep 7 - Sep 8
Total with taxes and fees
Shore Haven Inn
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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

Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent
"Surprisingly good place to stay. The townhouse room served it's purpose for sure having two adult couples. The main thing is we would certainly stay again."
Robert 2-night trip
Posted 4 hours ago
Admiralty Inn & Suites - a Red Collection Hotel
Green Harbor Waterfront Lodging

Green Harbor Waterfront Lodging

8/10 Good
"Basic hotel room, clean but bring yr own water. Has a refrigerator that was cold on arrival as was the room. Good AC in my room but my niece’s wasn’t as good & had a mildew smell. I was on lake view -1st floor level which was fine but I could hear people above walking around until @ 11 pm. My niece was on upper level but had to deal with people’s car lights as that was the parking area. Decent place overall. Didn’t use the pool or other amenities."
Colleen 6-night trip
Posted 11 hours ago
Green Harbor Waterfront Lodging
Inn on the Square

Inn on the Square

8/10 Good
"very good gir the money (off season)"
William 1-night trip
Posted 2 days ago
Inn on the Square
Harbor View Hotel

Harbor View Hotel

10/10 Excellent
"We had an amazing stay and we can not wait to be back."
Sandrine 4-night trip
Posted 10 days ago
Harbor View Hotel
Faraway Martha's Vineyard

Faraway Martha's Vineyard

10/10 Excellent
"We came here on our anniversary and could not have picked a better place. The boutique-yet-full-service hotel is elegant and beautiful, with great taste everywhere and amazing ocean views. The heated (perfect temperature) pool and jacuzzi were a perfect spot to take a break at any time in the day, with relaxing and happy lounge music. Most importantly, the staff is highly well trained, educated, and devoted to service with a smile without the attitude sometimes found in premium hotels sometimes. Mattia (spelling?), Duna, Julian were amazing. Coffee in the room a great plus! Short walk from the ferry (3 minutes!) and in the center of the action makes this hard to beat. I would only add more obvious breakfast choices (most guests just go out to great options short walks away) to make this even more perfect. We will certainly be back."
Cesar 3-night trip
Posted 13 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. Iris Hotel Cape Cod: Hotel located near Cape Cod Beaches. Offers a snack bar/deli, an indoor pool, and free self parking. Sea Crest Beach Resort: Hotel, 2-minute walk from Cape Cod Beaches. Provides a children's pool, a seasonal outdoor pool, and a private beach. Falmouth Inn: Hotel located near Cape Cod Beaches. Features daily, a pool, and free self parking. Vineyard Harbor Motel - Private Beach: Hotel located near Cape Cod Beaches. Provides a seasonal outdoor pool, an indoor pool, and daily.
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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