Photo by William E Berry Jr.

Windsor Hotel Guide - Romantic Hotels in Windsor, Vermont

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Check availability on Windsor Romantic Hotels

Top Windsor Romantic Hotels

Brook Road Inn
Interior

Brook Road Inn

3.0 star property
8.8 out of 10, Excellent, (229)
"It was well kept, had everything we needed and the location was great. "
Brook Road Inn
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Exterior

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
9.0 out of 10, Wonderful, (730)
"Great place great scenery amazing staff"
The price is €117
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Inn at Weathersfield
Interior

The Inn at Weathersfield

4.0 star property
10.0 out of 10, Exceptional, (63)
"Great Inn."
The Inn at Weathersfield
Hanover Inn Dartmouth
Breakfast, lunch, dinner served; local cuisine

Hanover Inn Dartmouth

4.0 star property
9.6 out of 10, Exceptional, (857)
"Nice atmosphere. Great location. Friendly staff."
The price is €229
includes taxes & fees
17 Aug - 18 Aug
Hanover Inn Dartmouth
Two Queen Bed Standard Hotel room with outdoor heated pool 201
TV, books, offices

Two Queen Bed Standard Hotel room with outdoor heated pool 201

8.6 out of 10, Excellent, (12)
"Our room was easy to find and very clean. And the late check-in was very helpful."
The price is €139
includes taxes & fees
17 Aug - 18 Aug
Two Queen Bed Standard Hotel room with outdoor heated pool 201
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Exterior

107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool

8.0 out of 10, Very good, (6)
"The check in process was so easy, our room was clean and had everything we needed. We would definitely stay here again"
The price is €149
includes taxes & fees
7 Sept - 8 Sept
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Interior

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

9.0 out of 10, Wonderful, (22)
"Great rate for a place with all the basics!"
The price is €197
includes taxes & fees
24 Aug - 25 Aug
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Killington Grand Hotel
Exterior

Killington Grand Hotel

3.5 star property
8.8 out of 10, Excellent, (179)
"Awesome resort by the mountain definitely will go back"
Killington Grand Hotel
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (160)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is €321
includes taxes & fees
19 Aug - 20 Aug
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Microwave, oven, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (96)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
The price is €249
includes taxes & fees
18 Aug - 19 Aug
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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.

Top Windsor Hotel Reviews

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Sweet place. Clean and very nice people that work there. "
Emily 2-night trip
Posted 2 days ago
Align Inn Vermont

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.