Winchester Hotels with Swimming Pool

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Check availability on Winchester Hotels with Swimming Pools

Our top choices for Winchester hotels with a pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (961 reviews)
  • cleanliness
    Immerse in rejuvenating waters at this mountain-adjacent hotel featuring a pristine indoor pool and relaxing hot tub sanctuary.
The price is RM476
RM523 total
includes taxes & fees
28 Apr - 29 Apr
Hampton Inn Brattleboro

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (792 reviews)
  • cleanliness
    Relaxing indoor pool retreat with comfortable loungers sets the perfect stage for your Vermont ski getaway.
The price is RM584
RM642 total
includes taxes & fees
21 Apr - 22 Apr
Comfort Inn & Suites Brattleboro I-91

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Splash into comfort at this indoor pool oasis offering year-round aquatic escape in Keene.
The price is RM534
RM579 total
includes taxes & fees
19 Apr - 20 Apr
Keene Elm City Hotel, an Ascend Collection Hotel

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (72 reviews)
  • cleanliness
    Dive into summer luxury at this guesthouse's seasonal pool, complete with sauna and nearby bay views for a refreshing retreat.
The price is RM771
RM848 total
includes taxes & fees
16 Apr - 17 Apr
The Inn At Quail Run

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (490 reviews)
  • cleanliness
    Refreshing poolside retreat in Black Mountain with seasonal swimming and scenic garden views.
The price is RM428
RM471 total
includes taxes & fees
17 Apr - 18 Apr
Black Mountain Inn

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Splash into luxury at this hotel's sparkling indoor pool, complete with plush sun loungers and serene atmosphere.
The price is RM569
RM618 total
includes taxes & fees
16 Apr - 17 Apr
Best Western Plus Keene Hotel

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,010 reviews)
  • cleanliness
    Dive into a serene indoor pool retreat with hot tub and sauna, perfect for year-round relaxation near Wachusett Mountain.
The price is RM569
RM636 total
includes taxes & fees
19 Apr - 20 Apr
The Colonial Hotel

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
  • cleanliness
    Tranquil outdoor pool retreat complements this historic bed & breakfast with garden views and mountain adventures.
The price is RM986
RM1,085 total
includes taxes & fees
16 Apr - 17 Apr
Inn on Putney Road

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (375 reviews)
  • cleanliness
    Splash into serenity at this inviting indoor pool hotel, where year-round swimming meets complete comfort and relaxation.
The price is RM687
RM746 total
includes taxes & fees
23 Apr - 24 Apr
Hampton Inn & Suites Keene
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Choose what matters most at hotels with a pool in Winchester

Top Winchester Hotel Reviews

Frequently asked questions

What are some accommodation options with pools in Winchester?
The Colonial Hotel: Features a sauna, an indoor pool and free self parking. Colonial Motel And Spa: Offers a full-service spa, 2 indoor swimming pools and a sauna. Hampton Inn Brattleboro: Provides complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Comfort Inn & Suites Brattleboro I-91: Features buffet, an indoor pool and free self parking. Vikings Villages Resort: Features buffet, an indoor pool and free self parking.
What is there to see and do in Winchester?
Make a point to visit attractions such as Cass Pond and Rhododendron State Park. During your stay, visit sights such as New England Sweetwater Farm & Distillery, Winchester Speedpark and Pisgah State Park. Take in the natural beauty of Winchester with the lakeside setting.
When is the best time to book a hotel with a pool in Winchester?
Taking the local weather in Winchester into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.

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