Search Hotels with Swimming Pool in Windsor

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Check availability on Windsor Hotels with Swimming Pool

Our top choices for Windsor hotels with a pool

Indoor pool
Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2.0 star property
Newbury
9.4 out of 10, Exceptional, (46)
"Funky place, easy access, good lodging and very close to the ski area. Only thing missing was a hair dryer! Would definitely stay again!"
United States
Christopher
The price is ₹11,246
₹12,201 total
includes taxes & fees
11 Dec - 12 Dec
Hideaway Inn Mt.Sunapee
Indoor pool
Align Inn Vermont

Align Inn Vermont

2.5 star property
Quechee
9.4 out of 10, Exceptional, (1044)
"Overall great stay."
United States
Kathryn
The price is ₹10,529
₹11,582 total
includes taxes & fees
9 Jan - 10 Jan 2026
Align Inn Vermont
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1000)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is ₹17,385
₹22,427 total
includes taxes & fees
22 Dec - 23 Dec
On The River Inn
Indoor pool
Best Western Springfield Hotel

Best Western Springfield Hotel

2.5 star property
Springfield
8.8 out of 10, Excellent, (803)
"so clean and friendly it was a perfect stay!"
United States
Colette
The price is ₹12,879
₹14,167 total
includes taxes & fees
15 Dec - 16 Dec
Best Western Springfield Hotel
Outdoor pool, a heated pool
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 star property
Killington
9.2 out of 10, Wonderful, (956)
"Great place to stay!"
United States
Stephen
The price is ₹12,878
₹14,875 total
includes taxes & fees
11 Dec - 12 Dec
The Mountain Inn at Killington
Indoor pool
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 star property
West Lebanon
8.2 out of 10, Very good, (1001)
"Great stay "
Canada
Silvia
The price is ₹12,016
₹14,992 total
includes taxes & fees
23 Dec - 24 Dec
Fireside Inn & Suites West Lebanon
Outdoor pool, a heated pool, open 10:00 AM to 10:00 PM, pool umbrellas
North Star Lodge and Resort

North Star Lodge and Resort

2.0 star property
Killington
8.6 out of 10, Excellent, (1003)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort
2 indoor pools, free pool cabanas, pool loungers
Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

3.0 star property
Newbury
9.2 out of 10, Wonderful, (378)
"Corey, the front desk attendant, was excellent."
United States
Beth
The price is ₹14,512
₹17,212 total
includes taxes & fees
16 Dec - 17 Dec
Mountain Edge Suites at Sunapee, an Ascend Collection Hotel
Indoor pool, seasonal outdoor pool
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
Brownsville
9.0 out of 10, Wonderful, (777)
"Very welcoming, spacious, clean. Perfect for a family of 4. "
United States
Kathleen
The price is ₹10,720
₹13,157 total
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Indoor pool
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 star property
Cavendish
8.8 out of 10, Excellent, (922)
"Great place to stay while skiing at okemo"
United States
Ken
The price is ₹12,624
₹14,391 total
includes taxes & fees
14 Dec - 15 Dec
Pointe at Castle Hill Resort
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 Windsor Hotel Reviews

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"So kind and accommodating "
Kristie 1-night trip
Posted 14 hours ago
Align Inn Vermont

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Frequently asked questions

What are some accommodation options with pools in Windsor?
Fat Sheep Farm & Cabins: Offers a seasonal outdoor pool, an indoor pool and 4 restaurants. Woodstock Inn & Resort: Hotel, 1-minute walk from Killington Resort. Features daily, an outdoor pool and free self parking. Killington Mountain Lodge, Tapestry Collection by Hilton: Offers daily, an indoor pool and free self parking. The Mountain Inn at Killington: Offers complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Align Inn Vermont: Features daily, a pool and complimentary high-speed (wired) Internet access.
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.