Book the Best Hotels with POOL in Chilmark in 2026

Q: 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. Vineyard Harbor Motel - Private Beach : Hotel located near Cape Cod Beaches. Offers daily, a pool, and free self parking. Falmouth Inn : Hotel located near Cape Cod Beaches. Provides a seasonal outdoor pool, an indoor pool, and daily.

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

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Our top choices for Chilmark hotels with a pool

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.

CA $257 total

includes taxes & fees

Jul 8 - Jul 9

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 $305 total

includes taxes & fees

Jul 12 - Jul 13

Mariner Motel

Falmouth

Dive into seaside serenity at this coastal retreat with a sun-drenched pool oasis.

CA $275 total

includes taxes & fees

Jul 8 - Jul 9

Green Harbor Waterfront Lodging

East Falmouth

Seasonal waterfront pool creates summer magic at this Cape Cod retreat with a garden terrace.

CA $307 total

includes taxes & fees

Jul 12 - Jul 13

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Falmouth Heights Motor Lodge

Falmouth Heights

Splashing summer days at this Falmouth hotel's sparkling pool with loungers and beach bars nearby.

CA $405 total

includes taxes & fees

Jul 6 - Jul 7

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.

CA $323 total

includes taxes & fees

Jul 8 - Jul 9

Iris Hotel Cape Cod

Falmouth

Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.

CA $393 total

includes taxes & fees

Jul 19 - Jul 20

Inn on the Square

Falmouth

Sun-drenched days await at the indoor pool retreat where year-round swimming creates vacation bliss.

CA $385 total

includes taxes & fees

Jul 12 - Jul 13

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Choose what matters most at hotels with a pool in Chilmark

Breakfast included

4 stars

Top Chilmark Hotel Reviews

Inn on the Square

8/10 Good

"We have some mixed feelings. In our initial room, the sofa bed mechanism was broken and the mattress did not lay flat. Staff was very responsive; moved us to another large room with a rollaway bed and that worked out fine. Our second night, the fire alarm went off at about 11:00 PM and we were outside the building until 1:30. Many fire trucks and emergency vehicles appeared and we could view smoke rising from our end of the building but there was no official information shared with the guests while we waited. The general manager did not interact with guests at all unless asked a question directly, and even then she communicated very little. No apologies for the inconvenience or informational updates. To the hotel's credit, the following day we found, left in our room, a letter from management along with a bottle of French wine and little box of Ben and Bill's chocolate truffles and we were refunded the cost for that night's stay, along with an offer of a 20% discount on our next stay. We thought that was quite fair. Our first morning, we ate breakfast at Persy's, right on the site. It was convenient to the hotel but there are much better places within walking distance of the Inn to get much better prepared food. The decaf coffee at Percy's was almost undrinkable. The Inn is under new ownership. We wish them well and look forward to seeing what they do with the Inn in the future."

Sea Crest Beach Resort

8/10 Good

"convenient short drive from Boston with less traffic over Bourne Bridge. great location with pristine calm and warm water beach. great staff helping get settled on the beach with chairs and umbrella. fortunate to select room with patio first floor which was convenient. rooms were fine nothing scary or amazing. service at bar was quick. food services were slow and basic. great value"

Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent

"Found this great spot in Falmouth, an older property (you can see that they have been maintaining it) but the rooms were spotless rooms. The Inn is located on a main road but close to downtown, perfect location. We enjoyed our quick trip and intend to go back!"

Green Harbor Waterfront Lodging

8/10 Good

"Checking in was easy. The person at the reception was kind and helpful. Our room was smaller than expected but tidy. It was supposed to sleep 5 (1 king bed and a pull out couch). There weren't extra linens and the office was closed by the time we noticed. Some of the outlets did not work so we all had to share chargers to juice up the electronics. On a brighter note, the room was lake side and there were outdoor tables with umbrellas. The neighbors we encountered were friendly and the pool was excellent. We liked that it started at 3 feet for those who cannot swim. The water was warm and clean. It is great that it is also pet friendly. We would stay again but will be a little better prepared."

Mansion House Inn And Spa

10/10 Excellent

"The room was beautiful with comfortable bed and pillows. Large bathroom with nice toiletries. We also had a cute balcony porch. My daughter said the gym was wonderful. We unfortunately didn’t have a chance to use the hot tub. The staff downstairs at the desk were very helpful in instructing us about public transportation and any other questions we had about the community. Mansion House is a great place to stay and would definitely go back there again."

Harbor View Hotel

10/10 Excellent

"Property was Beautiful. Only downside was there is no Elevator in the area we stayed which was a pain being on 3rd floor with a baby/carrage etc. My fault for not checking ahead of time but other than that the place was great. Close walking distance to downtown Edgartown. Staff was very friendly and accomodating."

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. Vineyard Harbor Motel - Private Beach: Hotel located near Cape Cod Beaches. Offers daily, a pool, and free self parking. Falmouth Inn: 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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