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Check availability on Windsor Romantic Hotels

Tonight
3 May - 4 May
Tomorrow
4 May - 5 May
Next weekend
8 May - 10 May
In two weeks
15 May - 17 May

Our top choices for Windsor romantic hotels

Interior

180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
Hartford
8.0 out of 10, Very Good, (3 reviews)
"The house was absolutely beautiful. A unique mix of modern and 70’s. The layout was spot on . We were only there one night , a very quick stop over but it was so comfortable and cozy. The host was so easy to communicate with and was very accommodating. Plenty of room to sleep a large group and the views….you have to see in person. Stunning . I travel a lot and use VRBO for all of my travels. This was one of the best experiences I have had . I recommend 100%. "
United States
Mary Anne C.
The price is AED 1,065
AED 2,021 total
includes taxes & fees
4 May - 5 May
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
"3rd year at this listing, absolutely love it. Close to okemo and mount snow. Host got back to me very quickly when reached out to. "
United States
Jake D.
The price is AED 624
AED 1,325 total
includes taxes & fees
4 May - 5 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is AED 413
AED 1,114 total
includes taxes & fees
4 May - 5 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Property grounds

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is AED 413
AED 1,114 total
includes taxes & fees
6 May - 7 May
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Smart TV, fireplace, books

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is AED 509
AED 1,065 total
includes taxes & fees
4 May - 5 May
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Property grounds

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is AED 180
AED 819 total
includes taxes & fees
8 May - 9 May
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Exterior

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is AED 367
AED 926 total
includes taxes & fees
4 May - 5 May
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Exterior

Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Great location and great place!"
United States
Linda G.
The price is AED 349
AED 810 total
includes taxes & fees
4 May - 5 May
Cozy Studio Condo with Great Location, WiFi & Kitchenette
TV

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"The Nest at Hawk Ledges was a perfect summer getaway. The home provides comfort in a tranquil setting while being close enough to many summer adventures. We enjoyed relaxing in the bright, open home after taking many day trips to explore the area. What a gem!"
United States
Ben N.
The price is AED 716
AED 2,600 total
includes taxes & fees
19 May - 20 May
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Exterior

Two Double bed Hotel Room with outdoor heated pool 216

Two Double bed Hotel Room with outdoor heated pool 216
Killington
The price is AED 300
AED 480 total
includes taxes & fees
10 May - 11 May
Two Double bed Hotel Room with outdoor heated pool 216
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
"Room was clean and quiet. The bed was comfortable. Parking was easy. Location is good. Breakfast was basic. No hot food except do it yourself waffles. There were refrigerated breakfast sandwiches that were to be microwaved. Served our purpose perfectly."
Shari 1-night trip
Posted 15 hours ago
Align Inn Vermont

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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.