A snow-covered river valley with a bridge and a town.

Windsor Hotel Guide - Hotels with Pool in Windsor, Vermont

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Check availability on Windsor Hotels with Pool

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov

Our top choices for Windsor hotels with a pool

A cozy living room with a leather couch, a fireplace, and a television.

1. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
10.0 out of 10, Exceptional, (1 review)
"The Cabin in the Woods looks very rustic on the outside, but a cabin ine the woods should. Inside was a pleasant surprise. Full kitchen, large leather wrap around sofa to watch the LARGE flat-screen TV, large dining room table, 4 bedrooms, and 2 full baths made this a perfect get away place."
United States
Alvin
The price is €511
includes taxes & fees
2 Dec - 3 Dec
Cabin on the hill Ascutney Vt - 4 bedrooms
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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Choose what matters most at hotels with a pool in Windsor

Breakfast included
Hot tub

Top Windsor Hotel Reviews

Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

10/10 Excellent
"A really lovely hotel, clean, comfortable, well appointed, plenty of parking, great breakfast. I wish we could have stayed longer!"
Debra 1-night trip
Posted 4 hours ago
Fireside Inn & Suites West Lebanon

Frequently asked questions

What are some accommodation options with pools in Windsor?
Fat Sheep Farm & Cabins: Hotel, 1-minute walk from Killington Resort. Provides daily, an outdoor pool and free self parking. The Mountain Inn at Killington: Features daily, an indoor pool and free self parking. Align Inn Vermont: Offers free self parking, an indoor pool and complimentary wireless Internet access. Fireside Inn & Suites West Lebanon: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Woodstock Inn & Resort: Offers complimentary high-speed (wired) Internet access, an indoor pool and free self parking.
What is there to see and do in Windsor?
The picturesque setting of Connecticut River and Paradise Park showcase the area's natural beauty. During your stay, visit sights such as American Precision Museum, Harpoon Brewery and Mt Ascutney State Park.
When is the best time to book a hotel with a pool in Windsor?
Taking the local weather in Windsor 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 17°C, while the coldest months are January and February, with an average of -6°C. The snowiest months in Windsor are March, January, November and February, with each month seeing an average of 38 cm of snowfall.
What's the best way to travel around Windsor?
Knowing the transportation options in Windsor can help you enjoy the area beyond your hotel pool. If you want to venture outside the area, hop aboard a train at Windsor Station. Windsor might not have very many public transport options to choose from, so consider renting a car to explore more.