Search Hotels with Pool in Winchester

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Check availability on Winchester Hotels with Pool

Tonight
27 Feb - 28 Feb
Tomorrow
28 Feb - 1 Mar
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

Our top choices for Winchester hotels with a pool

Indoor pool, open 6:00 AM to 10:00 PM, pool loungers

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)
"Great stay pool was very nice"
United States
Patrick
The price is ฿3,704
฿4,019 total
includes taxes & fees
3 Mar - 4 Mar
Best Western Plus Keene Hotel
In-room safe, desk, iron/ironing board, free cots/infant beds

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very good, (987 reviews)
"Staff were great place was clean and nice. "
United States
Alex
The price is ฿3,387
฿3,675 total
includes taxes & fees
4 Mar - 5 Mar
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (948 reviews)
"Good breakfast, great staff and very good location "
United States
Valdeci
The price is ฿3,542
฿3,896 total
includes taxes & fees
5 Mar - 6 Mar
Hampton Inn Brattleboro
Indoor pool, pool loungers

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (770 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is ฿3,581
฿3,939 total
includes taxes & fees
1 Mar - 2 Mar
Comfort Inn & Suites Brattleboro I-91
Exterior

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (484 reviews)
"Instant check-in and check-out Very responsive and friendly staff. Clean and well maintained. Everything you need is provided. The room is spacious, and the beds are comfortable."
United States
Olga
The price is ฿3,076
฿3,384 total
includes taxes & fees
12 Mar - 13 Mar
Black Mountain Inn
Reception

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,000 reviews)
"Well-kept hotel with a great restaurant."
United States
Adam
The Colonial Hotel
Seasonal outdoor pool

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (72 reviews)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is ฿6,991
฿7,691 total
includes taxes & fees
2 Mar - 3 Mar
The Inn At Quail Run
Indoor pool

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1,000 reviews)
"Very clean room and super friendly staff!"
United States
Joanne
The price is ฿4,450
฿4,895 total
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express Hotel & Suites Brattleboro by IHG
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.
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Choose what matters most at hotels with a pool in Winchester

Breakfast included
4 stars

Top Winchester Hotel Reviews

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

10/10 Excellent
"We got in late and they were very accommodating. The beds were comfortable and breakfast was delicious! "
Melissa 1-night trip
Posted 5 days ago
Hampton Inn & Suites Greenfield

Frequently asked questions

What are some accommodation options with pools in Winchester?
The Colonial Hotel: Offers a sauna, an indoor pool and free self parking. Colonial Motel And Spa: Provides a full-service spa, 2 indoor swimming pools and a sauna. Hampton Inn Brattleboro: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Comfort Inn & Suites Brattleboro I-91: Offers buffet, an indoor pool and free self parking. Vikings Villages Resort: Offers 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 Barden State Wildlife Management Area and Rhododendron State Park. During your stay, visit sights such as New England Sweetwater Farm & Distillery, Winchester Speedpark and Richmond Town Hall. 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.