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

Hotels with Swimming Pool in Chilmark, Massachusetts

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Check availability on Chilmark Hotels with Swimming Pool

Tonight
Aug 21 - Aug 22
Tomorrow
Aug 22 - Aug 23
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Chilmark hotels with a pool

1. 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.
P8,101
P10,012 total
includes taxes & fees
Aug 31 - Sep 1
Admiralty Inn & Suites - a Red Collection Hotel

2. 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.
P8,570
P11,042 total
includes taxes & fees
Sep 7 - Sep 8
Falmouth Inn

3. Iris Hotel Cape Cod

Iris Hotel Cape Cod
Falmouth
  • Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
P8,385
P9,597 total
includes taxes & fees
Sep 7 - Sep 8
Iris Hotel Cape Cod

4. Mariner Motel

Mariner Motel
Falmouth
  • Dive into seaside serenity at this coastal retreat with a sun-drenched pool oasis.
P8,570
P9,809 total
includes taxes & fees
Aug 31 - Sep 1
Mariner Motel

5. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
P13,185
P15,486 total
includes taxes & fees
Sep 10 - Sep 11
Shore Haven Inn

6. 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.
P10,430
P13,378 total
includes taxes & fees
Sep 20 - Sep 21
Inn on the Square

7. 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.
P24,361
P27,212 total
includes taxes & fees
Sep 3 - Sep 4
Lamberts Cove Inn

8. 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.
P23,045
P26,650 total
includes taxes & fees
Sep 7 - Sep 8
Mansion House Inn And Spa

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.
P16,768
P19,191 total
includes taxes & fees
Sep 6 - Sep 7
Sands of Time Motor Inn & Harbor House
View all properties

Choose what matters most at hotels with a pool in Chilmark

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Chilmark Hotel Reviews

Harbor View Hotel

Harbor View Hotel

10/10 Excellent
"My stay at the Harbor View Hotel was outstanding , from the room, food, staff And ambiance. I certainly will stay again, a little pricy, but I would stay! Elizabeth Haley"
Elizabeth 5-night trip
Posted 1 hour ago
Harbor View Hotel
Mariner's Point Resort

Mariner's Point Resort

8/10 Good
"Good location. Facility is outdated but has everything needed for a good break."
Denis 2-night trip
Posted 1 hour ago
Mariner's Point Resort
Sea Crest Beach Resort

Sea Crest Beach Resort

8/10 Good
"Beautiful resort overall but standard room was outdated and in need of a few upgrades."
Josephine 2-night trip
Posted 4 hours ago
Sea Crest Beach Resort
Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent
"I have a great experience with this hotel. This is third time staying here. The staff is kind and allows me to check-in early. I plan to stay here next year, August 2027"
Markia 3-night trip
Posted 14 hours ago
Admiralty Inn & Suites - a Red Collection Hotel
Faraway Martha's Vineyard

Faraway Martha's Vineyard

8/10 Good
"I enjoyed my stay in the Chappy House – Room 409, a suite with its on entrance from the outside. It was very well appointed and similar to a spacious one bedroom apartment without the kitchen. Must be capable of maneuvering stone pathways and steps to access it. Very nice for a long-term stay. I’d be interested in purchasing one! (Luxury vinyl plank flooring needs repairing in one hallway spot — barely noticeable.) 🙂"
Fred 1-night trip
Posted 1 day ago
Faraway Martha's Vineyard

Frequently asked questions

What are some accommodations with pools in Chilmark?
Iris Hotel Cape Cod: Features complimentary wireless internet access, a pool, and Smart TVs. Sea Crest Beach Resort: Hotel located near Cape Cod Beaches. Offers a snack bar/deli, an indoor pool, and free self parking. Falmouth Inn: Hotel, 2-minute walk from Cape Cod Beaches. Provides a children's pool, a seasonal outdoor pool, and a private beach. Summercamp: 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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