Photo by Donny Campos

Search Hotels with Pool in Winchester

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 Pool

Top Winchester Hotels with Pool

Front of property
Inn on Putney Road

Inn on Putney Road

4.0 star property
Brattleboro
  • Breakfast included
  • Spa
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
9.8 out of 10, Exceptional, (56)
Refreshing dips await with access to both indoor and outdoor pools near this upscale riverside retreat. Guests savour exceptional creative breakfasts while enjoying garden views, massage services, and adventures from kayaking to skiing.
The price is Rp4.455.962
Rp4.901.525 total
includes taxes & fees
16 Nov - 17 Nov
Inn on Putney Road
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, (728)
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 Rp1.745.255
Rp1.919.781 total
includes taxes & fees
17 Nov - 18 Nov
Comfort Inn & Suites Brattleboro I-91
Seasonal outdoor pool
The Inn At Quail Run

The Inn At Quail Run

2.5 star property
Wilmington
  • Pool
  • Parking included
  • Free WiFi
  • Gym
  • Game room
  • Laundry
9.0 out of 10, Wonderful, (71)
Seasonal swimming adventures await at this bayfront guesthouse from June through September. Beyond the outdoor pool, guests discover arcade games, billiards, and a relaxing sauna for post-swim rejuvenation.
The price is Rp3.088.390
Rp3.397.229 total
includes taxes & fees
14 Nov - 15 Nov
The Inn At Quail Run
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 Rp1.606.071
Rp1.766.677 total
includes taxes & fees
1 Dec - 2 Dec
Black Mountain Inn
Indoor pool
The Colonial Hotel

The Colonial Hotel

3.0 star property
Gardner
  • Indoor pool
  • Hot tub
8.8 out of 10, Excellent, (1000)
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
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Restaurant
9.0 out of 10, Wonderful, (104)
Sparkling pool waters beckon after exploring nearby hiking trails or skiing adventures. Massage services, garden views, and delightful cooked-to-order breakfasts complete the mountain retreat experience at this charming bed & breakfast.
The price is Rp5.027.231
Rp5.454.598 total
includes taxes & fees
16 Nov - 17 Nov
Chesterfield Inn
Indoor pool
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 star property
Keene
  • Indoor pool
8.8 out of 10, Excellent, (343)
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 Rp2.644.330
Rp2.869.098 total
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn & Suites Keene
Pool
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 star property
Greenfield
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Air conditioning
8.6 out of 10, Excellent, (873)
Swimming in the saltwater pool offers unexpected refreshment after exploring nearby attractions. Sound-insulated rooms ensure peaceful nights, while the fitness centre provides additional recreation options. Guests consistently praise the friendly staff and delicious breakfast selection.
The price is Rp2.390.581
Rp2.670.279 total
includes taxes & fees
19 Nov - 20 Nov
Hampton Inn & Suites Greenfield
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, (1003)
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 Rp2.236.996
Rp2.460.696 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express Hotel & Suites Brattleboro by IHG
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, (1001)
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 Rp2.487.406
Rp2.698.919 total
includes taxes & fees
16 Nov - 17 Nov
Best Western Plus Keene Hotel
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

Colonial Motel And Spa

Colonial Motel And Spa

10/10 Excellent
"YES, the room was SPOTLESS!!! An indoor Pool, Sauna & Continental Breakfast made this stay a PLUS!!! (Waffles, Toast, Coffee, Bagels, Cereal & Fresh Fruit). A definite choice for another visit!!!"
Barbara 1-night trip
Posted 13 days ago
Colonial Motel And Spa

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. The Covered Bridge Inn: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Travelodge by Wyndham Brattleboro VT: Offers sunloungers, a communal pool and complimentary wireless Internet access. Hampton Inn Brattleboro: Features buffet, an indoor pool and free self parking. Best Western Plus Keene Hotel: Offers buffet, a pool and complimentary high-speed (wired) Internet access.
What is there to see and do in Winchester?
Spend some time experiencing the great outdoors at Rhododendron State Park and Ashuelot River. During your stay, visit sights such as Pisgah State Park, New England Sweetwater Farm & Distillery and Conant Public Library. 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.