Hotels with Swimming Pool in Winchester, New Hampshire

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Check availability on Winchester Hotels with Swimming Pool

Our top choices for Winchester hotels with a pool

Indoor pool, sun 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, (740)
"Price, clean and spacious room, comfy bed."
United States
June
The price is P6,566
P7,223 total
includes taxes & fees
Dec 21 - Dec 22
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, (963)
"The room was perfect, and the food was great "
United States
Paul
The price is P6,922
P7,510 total
includes taxes & fees
Dec 21 - Dec 22
Keene Elm City Hotel, an Ascend Collection Hotel
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, (1001)
"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 P8,462
P9,308 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Indoor pool
Hampton Inn Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (926)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is P8,620
P9,481 total
includes taxes & fees
Dec 28 - Dec 29
Hampton Inn Brattleboro
Exterior
Black Mountain Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (474)
"Clean, very friendly staff. Will stay again."
United States
Scot
The price is P6,006
P6,607 total
includes taxes & fees
Dec 23 - Dec 24
Black Mountain Inn
Indoor pool, open 6:00 AM to 10:00 PM, sun 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, (1000)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is P7,580
P8,225 total
includes taxes & fees
Dec 21 - Dec 22
Best Western Plus Keene Hotel
Indoor pool
The Colonial Hotel

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1003)
"Easy checkin, pleasant staff and clean room. "
United States
Susan
The Colonial 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, (353)
"Clean comfy nice staff "
United States
Katherine
The price is P9,677
P10,499 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn & Suites Keene
2 indoor pools
Colonial Motel And Spa

Colonial Motel And Spa

Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1001)
"Nice place to stay for the night."
United States
Robin
The price is P6,753
P7,429 total
includes taxes & fees
Dec 21 - Dec 22
Colonial Motel And Spa
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 P10,283
P11,312 total
includes taxes & fees
Dec 23 - Dec 24
The Inn At Quail Run
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

Econo Lodge Brattleboro

Econo Lodge Brattleboro

8/10 Good
"Shops nearby. Heater worked good. 0lder motel but kept up quite well."
Janet 2-night trip
Posted 3 days ago
Econo Lodge Brattleboro

Frequently asked questions

What are some accommodations with pools in Winchester?
The Colonial Hotel: Features a sauna, an indoor pool, and free self parking. Hampton Inn & Suites Greenfield: Features complimentary wired internet access, an indoor pool, and free self parking. The Covered Bridge Inn: Offers buffet, an indoor pool, and free self parking. Hampton Inn Brattleboro: Features buffet, an indoor pool, and complimentary wired internet access. Comfort Inn & Suites Brattleboro I-91: Offers buffet, an indoor pool, and free self parking.
What is there to see and do in Winchester?
Make a point to visit attractions like Birch Point and Rhododendron State Park. During your stay, check out sights such as New England Sweetwater Farm & Distillery, Winchester Speedpark, and Bennett Gorge. 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 into account the local weather in Winchester can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.

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