Search Hotels with Pool in Winchester

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Check availability on Winchester Hotels with Pool

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winchester hotels with a pool

Indoor pool, pool loungers
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (746)
"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
United States
Jack
The price is ฿3,731
฿4,104 total
includes taxes & fees
31 Dec - 1 Jan 2026
Comfort Inn & Suites Brattleboro I-91
Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel

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, (968)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is ฿3,853
฿4,181 total
includes taxes & fees
28 Dec - 29 Dec
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool
Hampton Inn Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (928)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is ฿4,561
฿5,017 total
includes taxes & fees
3 Jan - 4 Jan 2026
Hampton Inn Brattleboro
Indoor pool
Holiday Inn Express Hotel & Suites Brattleboro by IHG

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, (1000)
"Very clean room, gentlemen at the front desk were welcoming and professional and the coffee was amazing! We are frequent visitors with you; we love IHG hotels. "
United States
Belinda
The price is ฿4,469
฿4,916 total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Indoor pool
The Colonial Hotel

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1000)
"Easy checkin, pleasant staff and clean room. "
United States
Susan
The Colonial Hotel
Seasonal outdoor pool
The Inn At Quail Run

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (71)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is ฿6,983
฿7,681 total
includes taxes & fees
3 Jan - 4 Jan 2026
The Inn At Quail Run
Exterior
Black Mountain Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (475)
"Clean, very friendly staff. Will stay again."
United States
Scot
The price is ฿3,076
฿3,384 total
includes taxes & fees
29 Dec - 30 Dec
Black Mountain Inn
Indoor pool, open 6:00 AM to 10:00 PM, pool loungers
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1001)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ฿4,319
฿4,686 total
includes taxes & fees
28 Dec - 29 Dec
Best Western Plus Keene Hotel
Indoor pool
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (358)
"Clean comfy nice staff "
United States
Katherine
The price is ฿5,150
฿5,588 total
includes taxes & fees
25 Jan - 26 Jan 2026
Hampton Inn & Suites Keene
Front of property
Inn on Putney Road

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is ฿7,281
฿8,009 total
includes taxes & fees
5 Jan - 6 Jan 2026
Inn on Putney Road
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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Top Winchester Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
Jack 1-night trip
Posted 4 days ago
Comfort Inn & Suites Brattleboro I-91

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. Hampton Inn & Suites Greenfield: Features buffet, an indoor pool and free self parking. The Covered Bridge Inn: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. Comfort Inn & Suites Brattleboro I-91: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Keene Elm City Hotel, an Ascend Collection Hotel: Offers continental, a seasonal outdoor pool and free self parking.
What is there to see and do in Winchester?
Make a point to visit attractions such as Birch Point and Rhododendron State Park. During your stay, visit sights such as Winchester Speedpark, Bennett Gorge 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.