Find Hotels with a Pool in Windsor, VT

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 Windsor Hotels with a 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 NT$3,976
NT$4,314 total
includes taxes & fees
Dec 11 - Dec 12
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 NT$3,620
NT$3,982 total
includes taxes & fees
Jan 9 - 2026/1/10
Align Inn Vermont
Indoor pool
Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon

3.0 star property
Lebanon
9.0 out of 10, Wonderful, (1001)
"This hotel is solid. Location relative to Hanover is good, facility is nice, and it’s clean and comfortable. Would definitely stay again. "
United States
Merridith
The price is NT$3,457
NT$3,751 total
includes taxes & fees
Dec 18 - Dec 19
Hilton Garden Inn Hanover Lebanon
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 NT$4,462
NT$4,909 total
includes taxes & fees
Dec 16 - Dec 17
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 NT$4,462
NT$5,154 total
includes taxes & fees
Dec 11 - Dec 12
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, (1000)
"Great stay "
Canada
Silvia
The price is NT$4,378
NT$5,427 total
includes taxes & fees
Dec 15 - Dec 16
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, (1000)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort
2 indoor pools, free cabanas, sun 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 NT$5,023
NT$5,958 total
includes taxes & fees
Dec 16 - Dec 17
Mountain Edge Suites at Sunapee, an Ascend Collection Hotel
Indoor pool, open 8:00 AM to 10:00 PM, sun 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 NT$6,018
NT$7,763 total
includes taxes & fees
Dec 22 - Dec 23
On The River Inn
Indoor pool
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 star property
Cavendish
8.8 out of 10, Excellent, (923)
"Great place to stay while skiing at okemo"
United States
Ken
The price is NT$5,270
NT$6,008 total
includes taxes & fees
Dec 11 - Dec 12
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.
View all properties

Top Windsor Hotel Reviews

North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"Location is very convenient. Service as described online."
Yilun 2-night trip
Posted 4 days ago
North Star Lodge and Resort

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations 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 wired internet access, an indoor pool, and free self parking. Align Inn Vermont: Features daily, a pool, and complimentary 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, check out 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 into account the local weather in Windsor can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 62°F, while the coldest months are January and February with an average of 22°F. The snowiest months in Windsor are March, January, November, and February, with each month seeing an average of 15 inches 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. To venture out into the surrounding area, hop aboard a train at Windsor Station. Windsor might not have very many public transportation choices so consider renting a car to explore more.