Photo by Donny Campos

Hotels with Pool & Resorts in Winchester from AU$207

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Winchester Hotels with Pool

Best Winchester Hotels with Pool

Keene Elm City Hotel, Ascend Hotel Collection
Indoor pool

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very good, (878)
"Staff were friendly, room clean and comfortable "
The price is AU$209
includes taxes & fees
24 Aug - 25 Aug
Keene Elm City Hotel, Ascend Hotel Collection
The Colonial Hotel
Indoor pool

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1000)
"We have stayed at this property a few times and it is always a pleasant experience. "
The Colonial Hotel
Best Western Plus Keene Hotel
Indoor pool, open 6:00 AM to 10:00 PM, pool loungers

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very good, (1008)
"Really enjoyed everything about my stay"
The price is AU$248
includes taxes & fees
24 Aug - 25 Aug
Best Western Plus Keene Hotel
Hampton Inn & Suites Keene
Indoor pool

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (328)
"Great hotel with friendly staff"
The price is AU$262
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Keene
Hampton Inn & Suites Greenfield
Pool

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (833)
"Great place with a walkable eating option"
The price is AU$261
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Greenfield
Comfort Inn & Suites Brattleboro I-91
Indoor pool, pool loungers

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (670)
"Great place for a quick stay with my son on the way to Maine. "
The price is AU$236
includes taxes & fees
19 Aug - 20 Aug
Comfort Inn & Suites Brattleboro I-91
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Indoor pool

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (1000)
"Good room, great breakfast options "
The price is AU$287
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Black Mountain Inn
Exterior

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (456)
"The bed was super comfortable and the sheets were very soft and also comfortable. "
The price is AU$211
includes taxes & fees
26 Aug - 27 Aug
Black Mountain Inn
Hampton Inn Brattleboro
Indoor pool

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (865)
"Great place for a quick over night stay. "
The price is AU$207
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn Brattleboro
Colonial Motel And Spa
2 indoor pools

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1004)
"Always a pleasure to stay at the Colonial"
The price is AU$237
includes taxes & fees
18 Aug - 19 Aug
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.

Top Winchester Hotel Reviews

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

10/10 Excellent
"🤘"
Shawn 1-night trip
Posted 2 days ago
Keene Elm City Hotel, Ascend Hotel Collection

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. Keene Elm City Hotel, Ascend Hotel Collection: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Putney Inn: Provides 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 Richmond Wildlife Manangement Area and Rhododendron State Park. During your stay, visit sights such as New England Sweetwater Farm & Distillery, Pisgah State Park and Ashuelot River. 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.