Find Hotels with an Outdoor Pool in Windsor, VT
- Upfront pricingOur total price for your stay includes taxes and fees
- Treat yourselfSave 10% or more on over 100,000 hotels worldwide with Member Prices
- Be pickySearch almost a million properties worldwide
Check availability on Windsor Hotels with an Outdoor Pool
Our top choices for Windsor hotels with an outdoor pool

8.4 out of 10, Very Good, (928)
$114 nightly
The price is $124
Dec 21 - Dec 22
Total with taxes and fees

8.6 out of 10, Excellent, (1001)
$160 nightly
The price is $176
Jan 4 - Jan 5, 2026
Total with taxes and fees
$168 nightly
The price is $184
Jan 6 - Jan 7, 2026
Total with taxes and fees

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Holiday Inn Club Vacations Mount Ascutney Resort by IHGBrownsville
9.0 out of 10, Wonderful, (778)
$134 nightly
The price is $146
Dec 18 - Dec 19
Total with taxes and fees

9.2 out of 10, Wonderful, (958)
$272 nightly
The price is $299
Dec 17 - Dec 18
Total with taxes and fees
$193 nightly
The price is $212
Dec 17 - Dec 18
Total with taxes and fees

Historic 150-year-old farmhouse, Jacuzzi included
Historic 150-year-old farmhouse, Jacuzzi includedChester Depot
9.8 out of 10, Exceptional, (10)
$419 nightly
The price is $469
Dec 14 - Dec 15
Total with taxes and fees

$330 nightly
The price is $363
Dec 16 - Dec 17
Total with taxes and fees
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.
Top Windsor Hotel Reviews

Pointe at Castle Hill Resort
10/10 Excellent
Explore a world of travel with Expedia
- Hotels near Windsor Station
- Hotels near South Congregational Church
- Hotels near American Precision Museum
- Hotels near Harpoon Brewery
- Hotels near Mt Ascutney State Park
- Hartland Hotels
- Hotels near Mount Ascutney
- 4 Star Hotels in Hartland
- Cabin Rentals in Hartland
- B&B in Hartland
- Motels in Hartland
- Resorts in Hartland
- Resorts & Hotels with Spas in Brownsville
- Pet-friendly Hotels in Brownsville
- Hotel Wedding Venues Hotels in Brownsville
- Ski Hotels in Brownsville
- Hotels with Tennis Courts in Brownsville
- Hotels with an Indoor Pool in Brownsville
- Ascutney Hotels
- B&B in Ascutney
- Apartments in Ascutney
- Condo Rentals in Ascutney
- Motels in Ascutney
- Cabin Rentals in Ascutney
- Brownsville Hotels
- Resorts in Brownsville
- Villas in Brownsville
- B&B in Brownsville
- Hotels with Free Breakfast in Perkinsville
- Perkinsville Hotels
- Cottages in Perkinsville
- B&B in Perkinsville
- Cabin Rentals in Perkinsville
- Resorts in Perkinsville
- Weathersfield Hotels
- Cabin Rentals in Weathersfield
- Motels in Weathersfield
- B&B in Weathersfield
- South Woodstock Hotels
- B&B in South Woodstock
- Cottages in South Woodstock
- Farmstay in South Woodstock
- Cabin Rentals in South Woodstock
- 5 Star Hotels in South Woodstock
- Ski Hotels in Reading
- Reading Hotels
- Cottages in Reading
- Resorts in Reading
- 3 Star Hotels in Reading
- Condo Rentals in Reading
- Hotels near Green Mountain Rock Climbing Center
- Resorts & Hotels with Spas in Cavendish
- Luxury Hotels in Cavendish
- Family Hotels in Cavendish
- Hotels with a Pool in Cavendish
- Hotel Wedding Venues Hotels in Cavendish
- Ski Hotels in Cavendish
- Hotels near Quechee Gorge Village
- Hotels near Quechee Gorge Bridge
- Woodstock Hotels
- Hotels near Quechee State Park
- Taftsville Hotels
- Old Constitution House
- American Precision Museum
- Paradise Park
- Brownsville Trail
- Mt Ascutney State Park
- Visit Hartland
- Visit Brownsville
- Brownsville Vacations
- Visit Perkinsville
- Visit Weathersfield
- Visit South Woodstock
- Visit Reading
- Reading Vacations
- Green Mountain Rock Climbing Center
- Quechee Gorge Village
- Quechee Gorge Bridge
- Quechee State Park
- Visit Taftsville










































