Winchester Hotels with Swimming Pool

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Hotels with Swimming Pools

Top Winchester Hotels with Swimming Pools

Indoor pool
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 star property
Brattleboro
8.2 out of 10, Very good, (920)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is RM380
RM418 total
includes taxes & fees
7 Dec - 8 Dec
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, (728)
"Absolutely perfect stay for a business trip"
United States
Lyndsey
The price is RM459
RM505 total
includes taxes & fees
7 Dec - 8 Dec
Comfort Inn & Suites Brattleboro I-91
Indoor pool
The Colonial Hotel

The Colonial Hotel

3.0 star property
Gardner
8.8 out of 10, Excellent, (1004)
"Great hotel, fantastic restaurant, wonderful place!"
United States
Kate
The Colonial Hotel
Indoor pool
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, (949)
"Enjoyed the breakfast options and the very comfortable bed. "
Canada
Nancy
The price is RM490
RM531 total
includes taxes & fees
10 Dec - 11 Dec
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

2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1000)
"Friendly, efficient staff and a very clean and nice room"
United States
Margaret
The price is RM495
RM545 total
includes taxes & fees
23 Nov - 24 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Indoor pool
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 star property
Keene
8.8 out of 10, Excellent, (347)
"Nice place to stay, nice area, will stay again."
United States
Catherine
The price is RM630
RM683 total
includes taxes & fees
28 Nov - 29 Nov
Hampton Inn & Suites Keene
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, (1001)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is RM577
RM626 total
includes taxes & fees
24 Nov - 25 Nov
Best Western Plus Keene Hotel
Exterior
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 RM400
RM440 total
includes taxes & fees
1 Dec - 2 Dec
Black Mountain Inn
2 indoor pools
Colonial Motel And Spa

Colonial Motel And Spa

3.0 star property
Brattleboro
6.8 out of 10, (1002)
"Nice place to stay for the night."
United States
Robin
The price is RM498
RM548 total
includes taxes & fees
23 Nov - 24 Nov
Colonial Motel And Spa
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.
View all properties

Top Winchester Hotel Reviews

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"In town for an afternoon event and pleasantly surprised when we were able to check in at 1PM. Room is spacious with a nice layout, clean and nice bathroom. We're only here for one night; kind of wish we were staying longer!"
Jim 1-night trip
Posted 4 days ago
Courtyard by Marriott Keene Downtown

Explore a world of travel with Expedia

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 Brattleboro: Offers complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Hampton Inn & Suites Greenfield: Features buffet, an indoor pool and free self parking. Comfort Inn & Suites Brattleboro I-91: Provides buffet, an indoor pool and free self parking. The Covered Bridge Inn: 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 Birch Point and Rhododendron State Park. During your stay, visit 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 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.