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

Chilmark Hotel Guide - Hotels with Pool in Chilmark, Massachusetts

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Check availability on Chilmark Hotels with Pool

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

Our top choices for Chilmark hotels with a pool

1. Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
Cozy efficiency apartment/heated pool

2. 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.
€139
includes taxes & fees
20 Sept - 21 Sept
Admiralty Inn & Suites - a Red Collection Hotel

3. 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.
€153
includes taxes & fees
7 Sept - 8 Sept
Falmouth Inn

4. Iris Hotel Cape Cod

Iris Hotel Cape Cod
Falmouth
  • Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
€133
includes taxes & fees
7 Sept - 8 Sept
Iris Hotel Cape Cod

5. Mariner Motel

Mariner Motel
Falmouth
  • Dive into seaside serenity at this coastal retreat with a sun-drenched pool oasis.
€136
includes taxes & fees
7 Sept - 8 Sept
Mariner Motel

6. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
€215
includes taxes & fees
10 Sept - 11 Sept
Shore Haven Inn

7. Inn on the Square

Inn on the Square
Falmouth
  • Sun-drenched days await at the indoor pool retreat where year-round swimming creates holiday bliss.
€186
includes taxes & fees
20 Sept - 21 Sept
Inn on the Square

8. 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.
€378
includes taxes & fees
3 Sept - 4 Sept
Lamberts Cove Inn

9. 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.
€370
includes taxes & fees
7 Sept - 8 Sept
Mansion House Inn And Spa

10. 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.
€266
includes taxes & fees
1 Sept - 2 Sept
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

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 2 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 13 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 accommodation options with pools in Chilmark?
Cozy efficiency apartment/heated pool: Features complimentary wireless Internet access, a pool and Smart televisions. 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. Summercamp: 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, visit 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 the local weather in Chilmark into account can help you maximise your time at the pool during your trip. The hottest months are usually August and July, with an average temperature of 20°C, while the coldest months are February and January, with an average of 3°C. Average annual precipitation for Chilmark is 1272 mm.