Photo by William E Berry Jr.

Most Romantic Hotels in Windsor

    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
19 Jul - 20 Jul
Tomorrow
20 Jul - 21 Jul
Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug

Top Windsor Romantic Hotels

Frequently asked questions

Searching for romantic hotels in Windsor?
Are you in need of a romantic holiday? If you want to explore the area, you might head to Harpoon Brewery, Mt Ascutney State Park or Connecticut River. If you're interested in staying close to a particular destination, you can sort properties by neighbourhood and proximity to top sights, so you'll be able to see everything on your list.
What's the best place to stay for a romantic holiday in Windsor?
Windsor Mansion Inn is a favourite 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, take a look at these details about year-round temperatures in Windsor: The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -6°C. The snowiest months in Windsor are March, January, November and February, with each month seeing an average of 38 cm of snowfall.
What is there to do in Windsor?
There's nothing better than wandering around 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 centre. To venture out into the surrounding area, take a train from Windsor Station.