Hotels with Swimming Pools in Winchester

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Check availability on Winchester Hotels with Swimming Pools

Tonight
27 Nov - 28 Nov
Tomorrow
28 Nov - 29 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Hotels with Swimming Pools in Winchester

Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
Keene
  • Indoor pool
8.4 out of 10, Very good, (952)
Invigorating swims await at the pristine indoor pool, accessible from early morning until late evening. Guests praise the super comfortable beds, friendly staff, and excellent breakfast buffet at this well-located hotel near shopping and dining options.
The price is S$153
includes taxes & fees
17 Dec - 18 Dec
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool, pool loungers
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 star property
Brattleboro
  • Indoor pool
  • Pool loungers
8.6 out of 10, Excellent, (732)
Mountain adventures meet poolside relaxation at this Brattleboro hotel. Swimmers enjoy the indoor pool with plush sun loungers year-round, while winter enthusiasts appreciate easy access to cross-country and downhill skiing trails.
The price is S$172
includes taxes & fees
7 Dec - 8 Dec
Comfort Inn & Suites Brattleboro I-91
Indoor pool
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 star property
Brattleboro
  • Indoor pool
  • Hot tub
8.2 out of 10, Very good, (923)
Soothing waters welcome weary skiers and travellers in the immaculate indoor pool and hot tub area. Fitness enthusiasts appreciate the well-maintained exercise facility while enjoying proximity to local ski mountains, restaurants, and recreational activities.
The price is S$204
includes taxes & fees
6 Dec - 7 Dec
Hampton Inn Brattleboro
Indoor pool
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
Brattleboro
  • Indoor pool
8.8 out of 10, Excellent, (1002)
Splashing fun awaits in the indoor pool, open from 5 AM to 11 PM daily, complementing winter activities like nearby skiing and snowboarding. Families appreciate the arcade room while fitness enthusiasts enjoy the 24-hour gym.
The price is S$182
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Indoor pool
The Colonial Hotel

The Colonial Hotel

3.0 star property
Gardner
  • Indoor pool
  • Hot tub
8.8 out of 10, Excellent, (1010)
Vibrant indoor aquatic sanctuary awaits with a pristine pool, rejuvenating hot tub, and calming sauna. Families appreciate the kid-friendly atmosphere while adventure seekers enjoy nearby hiking trails and winter sports after refreshing swims.
The Colonial Hotel
Indoor pool
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 star property
Keene
  • Indoor pool
8.8 out of 10, Excellent, (349)
Swimmers glide through crystalline waters in the immaculate indoor pool, a cherished sanctuary regardless of season. Complementing this aquatic haven, the hotel boasts a 24-hour fitness centre, billiards table, and highly praised complimentary breakfast buffet.
The price is S$207
includes taxes & fees
24 Dec - 25 Dec
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
  • Indoor pool
  • Pool loungers
8.4 out of 10, Very good, (1006)
Aquatic relaxation awaits at the pristine indoor pool, complete with comfortable loungers and convenient 6:00 AM to 10:00 PM access. Beyond swimming, guests praise the plentiful breakfast options, exceptionally clean rooms, and hiking trails nearby.
The price is S$196
includes taxes & fees
30 Nov - 1 Dec
Best Western Plus Keene Hotel
Exterior
Black Mountain Inn

Black Mountain Inn

2.0 star property
Brattleboro
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.4 out of 10, Good, (474)
Cooling waters of the seasonal outdoor pool invite relaxation after exploring hiking trails and mountain biking routes. Garden views create a peaceful retreat while friendly staff ensure a comfortable stay at this quiet mountain escape.
The price is S$157
includes taxes & fees
8 Dec - 9 Dec
Black Mountain Inn
2 indoor pools
Colonial Motel And Spa

Colonial Motel And Spa

3.0 star property
Brattleboro
  • 2 indoor pools
  • Hot tub
6.8 out of 10, (1003)
Swimming enthusiasts adore 2 indoor pools complemented by a rejuvenating hot tub with powerful jets. After mountain adventures or skiing excursions, guests retreat to the sauna, indulge in professional massages, and savour authentic Indian cuisine on-site.
The price is S$171
includes taxes & fees
30 Nov - 1 Dec
Colonial Motel And Spa
Indoor pool
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3.0 star property
Keene
  • Indoor pool
8.8 out of 10, Excellent, (1005)
Swimming enthusiasts revel in the indoor pool, open from 6:00 AM to 10:00 PM daily, complementing active adventures like hiking nearby trails. This Art Deco hotel's central location puts dining options and mountain recreation within easy reach.
The price is S$226
includes taxes & fees
5 Dec - 6 Dec
Courtyard by Marriott Keene Downtown
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

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Staff was very polite, the restaurant was lovely the service was amazing the room was comfortable and relaxing we loved it :)"
Lily 2-night trip
Posted 1 day ago
The Colonial Hotel

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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.