The Best Hotels with a Pool in Chilmark, MA from ￥24,758 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. AutoCamp Cape Cod : Offers 2 restaurants, a seasonal outdoor pool, and 2 bars. Summercamp : Provides 2 restaurants, a seasonal outdoor pool, and complimentary wired internet access.

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Our top choices for Chilmark hotels with a pool

Green Harbor Waterfront Lodging

East Falmouth

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

￥24,758 total

includes taxes & fees

Jun 15 - Jun 16

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.

￥27,798 total

includes taxes & fees

Jun 17 - Jun 18

Classic Double Room | Bathroom | Combined shower/tub, free toiletries, hair dryer, towels

Mariner Motel

Falmouth

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

￥25,491 total

includes taxes & fees

Jun 15 - Jun 16

Admiralty Inn & Suites - a Red Collection Hotel

East Falmouth

Dive into year-round aquatic bliss with indoor and seasonal outdoor pools in Cape Cod.

￥29,797 total

includes taxes & fees

Jun 21 - Jun 22

Iris Hotel Cape Cod

Falmouth

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

￥29,342 total

includes taxes & fees

Jun 17 - Jun 18

The Island Inn on Martha's Vineyard

Oak Bluffs

Experience island charm with a refreshing seasonal pool and tennis courts at this serene Martha's Vineyard retreat.

￥70,557 total

includes taxes & fees

Jun 15 - Jun 16

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.

￥34,661 total

includes taxes & fees

Jun 15 - Jun 16

New Seabury Cape Condo + Pool & Beach Escape

New Seabury

￥53,921 total

includes taxes & fees

Jun 17 - Jun 18

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Choose what matters most at hotels with a pool in Chilmark

Breakfast included

4 stars

Top Chilmark Hotel Reviews

Sea Crest Beach Resort

6/10 Okay

"My main complaint is check-in. We arrived at the resort at 3:00 pm. Check-in time is 4:00 pm. We did not get a room assignment until 5:30 pm; others didn't get rooms until 8:00 pm. This appeared to be an issue on this weekend. The part that really bothered me was that no one working behind the desk was apologetic or explained the delay. They just kept saying, "No, your room is not ready." I also explained when we arrived, we had an 87-year-old woman who had a hard time going up the stairs. I did not realize the resort had several buildings, and that only one had an elevator. The first person we spoke to upon arrival at 3:00 pm said they would try to help us out. Not all rooms were assigned at this point. When we got our room assignment at 5:30 pm, it was clear no one had even considered this. We were assigned a room on the second floor in the building furthest away from the main area. No problem for most, but it was for my 87-year-old mother. I did get them to switch the room to the main building. Due to this change, we did not have a patio with our room as we had paid for. I understand that the issue with my mother's limitations was not entirely the resort's fault, although I found their indifference to it disappointing. The room was okay, but in need of some repairs. The best thing I can say about the resort is that the location is great. The beach and pool areas are very nice. Also, the fries at the restaurant are good."

Admiralty Inn & Suites - a Red Collection Hotel

6/10 Okay

"This place hasn’t changed much.. at all actually since I stayed as a kid 20 years ago. You would think with all the solar panels on multiple roofs of the property they would invest in upgrading some things. Only reason I gave 3 instead of 2 is the staff were nice."

Faraway Martha's Vineyard

6/10 Okay

"Just came back from our stay here and have to say that we were a bit disappointed. This is definitely not one of the cheaper options to stay at on the island and so we had high hopes when we booked our stay. We've been coming to the Vineyard for years and have stayed at a number of different establishments. This was by far the biggest disappointment. That being said, it wasn't all bad. I feel like if given the opportunity they might be able to change our opinions as the facelift they gave to the place was amazing and definitely had a luxury feel to the place, but at their price point I would sooner try another place first. - Check in took 3 hours for our room to be ready even though they told us that the room was already cleaned and just needed to be inspected - Cleanliness at the pool was hit or miss, some days there would be people cleaning up old glasses and towels left behind, other days it was a mess - No elevator which wasn't an issue to us though we did have to carry our bags up three flights of stairs because they were short staffed - Our door never fully closed on it's own so we had to remember to slam it each time - No coffee in room which is fine but to not offer a decaf option or non-milk based creamers didn't exactly line up with their luxury aesthetic - Couldn't get hot water in our room, luke warm at best, chalked it up to old pipes in an old building - Be cautious if you stay in a room facing the Pelican club as they play loud music up to 11 p.m."

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. AutoCamp Cape Cod: Offers 2 restaurants, a seasonal outdoor pool, and 2 bars. Summercamp: Provides 2 restaurants, a seasonal outdoor pool, and complimentary wired internet access.

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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