The Best Hotels with a Pool in Chilmark, MA from ￥25,040 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. Private Hilltop Chilmark Estate with private tennis court, gym and hot tub : Hotel located near Cape Cod Beaches. Provides a snack bar/deli, an indoor pool, and free self parking. Iris Hotel Cape Cod : Hotel, 2-minute walk from Cape Cod Beaches. Features a children's pool, a seasonal outdoor pool, and a private beach. Sea Crest Beach Resort : Hotel located near Cape Cod Beaches. Offers daily, a pool, and free self parking. Falmouth Inn : Hotel located near Cape Cod Beaches. Offers 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

1. 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.

￥29,050 total

includes taxes & fees

Aug 30 - Aug 31

2. 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.

￥75,794 total

includes taxes & fees

Sep 1 - Sep 2

3. 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.

￥96,605 total

includes taxes & fees

Aug 31 - Sep 1

4. Inn on the Square

Falmouth

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

￥38,548 total

includes taxes & fees

Aug 30 - Aug 31

5. Admiralty Inn & Suites - a Red Collection Hotel

East Falmouth

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

￥25,559 total

includes taxes & fees

Aug 31 - Sep 1

6. Iris Hotel Cape Cod

Falmouth

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

￥35,848 total

includes taxes & fees

Aug 30 - Aug 31

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

7. Mariner Motel

Falmouth

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

￥25,040 total

includes taxes & fees

Aug 30 - Aug 31

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

8. Falmouth Heights Motor Lodge

Falmouth Heights

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

￥44,856 total

includes taxes & fees

Aug 9 - Aug 10

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Choose what matters most at hotels with a pool in Chilmark

Breakfast included

4 stars

Top Chilmark Hotel Reviews

Harbor View Hotel

10/10 Excellent

"We had an amazing stay and we can not wait to be back."

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."

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. Private Hilltop Chilmark Estate with private tennis court, gym and hot tub: Hotel located near Cape Cod Beaches. Provides a snack bar/deli, an indoor pool, and free self parking. Iris Hotel Cape Cod: Hotel, 2-minute walk from Cape Cod Beaches. Features a children's pool, a seasonal outdoor pool, and a private beach. Sea Crest Beach Resort: Hotel located near Cape Cod Beaches. Offers daily, a pool, and free self parking. Falmouth Inn: Hotel located near Cape Cod Beaches. Offers 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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