Photo by William E Berry Jr.

Find Romantic Hotels in Windsor, VT from $111

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Top Windsor Romantic Hotels

The Mountain Inn at Killington

2.5 star property
9.2 out of 10, Wonderful, (907)
"Nice accommodations, very inviting and friendly staff. "
$156 nightly
The price is $172
Oct 19 - Oct 20
Total with taxes and fees
The Mountain Inn at Killington

Pointe at Castle Hill Resort

3.5 star property
8.8 out of 10, Excellent, (898)
"It was a beautiful place "
$134 nightly
The price is $145
Nov 5 - Nov 6
Total with taxes and fees
Pointe at Castle Hill Resort

Brook Road Inn

3.0 star property
8.6 out of 10, Excellent, (238)
"I basically live here sometimes and it’s great. Foods not far either"
$102 nightly
The price is $111
Nov 2 - Nov 3
Total with taxes and fees
Brook Road Inn

Beautiful home offering privacy on 7 acres with private pond

10.0 out of 10, Exceptional, (30)
"Very relaxing house, we all enjoyed the fireplaces and pellet stove and the well-equipped kitchen allowed us to cook beautiful meals. The property is gorgeous and neighbors are far away. This was the perfect place for a friends reunion/ski trip!"
$455 nightly
The price is $509
Oct 8 - Oct 9
Total with taxes and fees
Beautiful home offering privacy on 7 acres with private pond

The Inn at Weathersfield

4.0 star property
9.8 out of 10, Exceptional, (66)
"Comfortable room and tasty dinner. Very well run."
$251 nightly
The price is $274
Oct 19 - Oct 20
Total with taxes and fees
The Inn at Weathersfield

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
9.0 out of 10, Wonderful, (757)
"It is Good place to stay. We enjoyed our stay here."
$182 nightly
The price is $198
Nov 2 - Nov 3
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Hanover Inn Dartmouth

4.0 star property
9.6 out of 10, Exceptional, (872)
"Perfect hotel "
$309 nightly
The price is $335
Nov 2 - Nov 3
Total with taxes and fees
Hanover Inn Dartmouth

Jackson Gore Village

3.0 star property
8.6 out of 10, Excellent, (781)
"This place is amazing!!! We wish we could stay for a week!"
$193 nightly
The price is $213
Nov 6 - Nov 7
Total with taxes and fees
Jackson Gore Village

Grafton Inn

3.5 star property
9.6 out of 10, Exceptional, (80)
"Wonderful in every way."
$253 nightly
The price is $275
Nov 5 - Nov 6
Total with taxes and fees
Grafton Inn

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (163)
"We very much enjoyed our stay, check in was a breeze and we found the cabin to be a cozy retreat. We have been looking for a place that had a bed and bath on first floor to accommodate some mobility limitations and this home was perfect having a single step on the front porch. We look forward to booking another trip with this host "
$330 nightly
The price is $370
Oct 13 - Oct 14
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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.

Find out more about Windsor

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 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.
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.

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