Photo by William E Berry Jr.

Romantic Hotels in Windsor, Vermont

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Windsor Romantic Hotels

Tonight
Jul 27 - Jul 28
Tomorrow
Jul 28 - Jul 29
Next weekend
Aug 1 - Aug 3
In two weeks
Aug 8 - Aug 10

Top Windsor Romantic Hotels

Top Windsor Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Peace and tranquility. Excellent staff. Very clean."
nche 2-night trip
Posted 2 weeks ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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 Harpoon Brewery, Mt Ascutney State Park, or Connecticut River. 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.
What's the best hotel for a romantic getaway to Windsor?
Windsor Mansion Inn is a favorite B&B for couples, and features premium bedding and wedding services.
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 Harpoon Brewery, Mt Ascutney State Park, or Connecticut River 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.