Find Romantic Hotels in Windsor, VT from $111

Start date: Check-in selected.
To Date
End date: Check-out
  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check availability on Windsor Romantic Hotels

This weekend
Next weekend

Top Windsor Romantic Hotels

Hilton Garden Inn Hanover Lebanon

3.0 star property
Lebanon
9.0 out of 10, Wonderful, (1005)
"Clean hotel, friendly staff and great area! Loved it and would highly recommend!!"
United States
Raymond Alan
$113 nightly
The price is $123
Dec 18 - Dec 19
Total with taxes and fees
Hilton Garden Inn Hanover Lebanon

Brook Road Inn

3.0 star property
Goshen
8.6 out of 10, Excellent, (243)
"A cozy and comfortable venue."
United States
Brian
$102 nightly
The price is $111
Nov 30 - Dec 1
Total with taxes and fees
Brook Road Inn

Hanover Inn Dartmouth

4.0 star property
Hanover
9.6 out of 10, Exceptional, (889)
"Perfect when visiting Dartmouth. Location, cozyness, seamless check-in & check-out, spotless rooms."
United States
Juan Pablo
$199 nightly
The price is $216
Dec 29 - Dec 30
Total with taxes and fees
Hanover Inn Dartmouth

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
Brownsville
9.0 out of 10, Wonderful, (776)
"Very welcoming, spacious, clean. Perfect for a family of 4. "
United States
Kathleen
$106 nightly
The price is $115
Dec 8 - Dec 9
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
Killington
7.4 out of 10, Good, (1000)
"We love it here."
United States
Vanessa L
$147 nightly
The price is $161
Dec 3 - Dec 4
Total with taxes and fees
Killington Mountain Lodge, Tapestry Collection by Hilton

The Common Man Inn & Restaurant

3.5 star property
Claremont
9.6 out of 10, Exceptional, (369)
"Wonderful place to stay "
United States
John
$139 nightly
The price is $151
Nov 30 - Dec 1
Total with taxes and fees
The Common Man Inn & Restaurant

Dexter's Inn

3.0 star property
Sunapee
8.8 out of 10, Excellent, (70)
"This was my 3rd time staying at Dexter’s Inn and hopefully not the last. It is a wonderful inn with easy access to Mount Sunapee. "
United States
Lisa
$235 nightly
The price is $256
Dec 1 - Dec 2
Total with taxes and fees
Dexter's Inn

The Mountain Inn at Killington

2.5 star property
Killington
9.2 out of 10, Wonderful, (949)
"Excellent hotel. "
United States
Kristan
$156 nightly
The price is $172
Nov 30 - Dec 1
Total with taxes and fees
The Mountain Inn at Killington

The Quechee Inn at Marshland Farm

3.0 star property
Quechee
9.0 out of 10, Wonderful, (1000)
"Beautiful historic property. We had dinner at the hotel restaurant and it was fantastic!"
United States
Dion
$169 nightly
The price is $186
Nov 30 - Dec 1
Total with taxes and fees
The Quechee Inn at Marshland Farm

Pointe at Castle Hill Resort

3.5 star property
Cavendish
8.8 out of 10, Excellent, (918)
"Clean room, great staff, wonderful suggestions for area restaurants and attractions."
United States
Margie
$146 nightly
The price is $159
Dec 4 - Dec 5
Total with taxes and fees
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.

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.

Find out more about Windsor

Windsor attractions for couples

Windsor, Vermont, offers a delightful mix of history, outdoor adventure, and charm perfect for families seeking quality experiences. Start your visit at the historic Old Constitution House, where you can delve into Vermont's revolutionary past and enjoy guided tours that appeal to both kids and adults. For outdoor enthusiasts, the nearby Mount Ascutney State Park provides miles of hiking trails with stunning vistas, ideal for a family day of exploration and picnicking. Don’t miss a stop at the Windsor-Cornish Covered Bridge, a picturesque spot that’s perfect for family photos and a leisurely stroll. The local art scene is vibrant, with places like the Artisans Park showcasing handcrafted goods and offering workshops where you can learn from skilled artisans. After a day of adventures, consider staying in the heart of Windsor, where cozy accommodations like the Norwich Inn offer attentive service and a warm atmosphere, ensuring you feel pampered after each day of exploration. With great dining options nearby, you can indulge in local cuisine while enjoying the quaint charm of this New England town.

Top Windsor Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Windsor?
Are you in need of a romantic escape? If you want to explore the area, you might head to American Precision Museum, Harpoon Brewery, or Mt Ascutney State Park. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Windsor?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Windsor: 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 is there to do in Windsor?
There's nothing better than experiencing a new place with your sweetheart, so consider taking time to discover all there is to see and do in Windsor. You might think about stopping by American Precision Museum, Harpoon Brewery, or Mt Ascutney State Park while you're seeing the sights.
What's the best way to get to Windsor and around town during my romantic getaway?
This information about transportation options in Windsor might help your romantic trip get off to a smooth start: To get to Windsor, you can fly into Lebanon, NH (LEB-Lebanon Municipal), which is the closest major airport, located 10.7 mi (17.3 km) from the city center. To see more of the larger area, ride aboard one of the trains from Windsor Station.

Explore a world of travel with Expedia