Luxury Hotels & Resorts in Windsor from AU$123

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Windsor Luxury Hotels

This weekend
Next weekend

Our top choices for Windsor luxury hotels

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,002 reviews)
"Brilliant stay"
United States
Enrico
The price is AU$425
includes taxes & fees
12 Feb - 13 Feb
On The River Inn

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
10.0 out of 10, Exceptional, (71 reviews)
"Wonderful experience, Wonderful staff. Thank you!"
United States
Patrick
The Inn at Weathersfield

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (263 reviews)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson

Hanover Inn Dartmouth

Hanover Inn Dartmouth
4.0 star property
Hanover
9.6 out of 10, Exceptional, (912 reviews)
"Friendly. Clean, good location"
United States
Deborah
The price is AU$352
includes taxes & fees
1 Feb - 2 Feb
Hanover Inn Dartmouth

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (561 reviews)
"Excellent hotel, staff well trained. "
United States
Christian
The price is AU$549
includes taxes & fees
22 Feb - 23 Feb
Woodstock Inn & Resort

The Birch Ridge: Family Room #6 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Hotel Room

The Birch Ridge: Family Room #6 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Hotel Room
4.0 star property
Killington
The Birch Ridge: Family Room #6 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Hotel Room

The Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home

The Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home
4.0 star property
Killington
The Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home

The Birch Ridge: American Classic Room #7 - King Suite In Killington. Hot Tub. 1 Bedroom Home

The Birch Ridge: American Classic Room #7 - King Suite In Killington. Hot Tub. 1 Bedroom Home
4.0 star property
Killington
The Birch Ridge: American Classic Room #7 - King Suite In Killington. Hot Tub. 1 Bedroom Home

The Birch Ridge: Colonial Maple Room #1 - Queen Suite In Renovated Killington Lodge 1 Bedroom Home

The Birch Ridge: Colonial Maple Room #1 - Queen Suite In Renovated Killington Lodge 1 Bedroom Home
4.0 star property
Killington
The Birch Ridge: Colonial Maple Room #1 - Queen Suite In Renovated Killington Lodge 1 Bedroom Home

The Birch Ridge: Lace Room #3 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home

The Birch Ridge: Lace Room #3 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home
4.0 star property
Killington
The Birch Ridge: Lace Room #3 - Queen Suite In Renovated Killington Lodge. Hot Tubs. 1 Bedroom Home
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

Frequently asked questions

Are you searching for a great accommodation for your luxury getaway to Windsor?
Expedia can help you arrange a flight to Lebanon, NH (LEB-Lebanon Municipal) airport or Springfield, VT (VSF-Hartness State) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay special. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Windsor offers. Windsor has some interesting things to see and do including Harpoon Brewery and Mt Ascutney State Park, so you might want to take in the local sights during your visit.
When can I expect good weather in Windsor?
Planning for the weather is an important factor for making your trip to Windsor a success, especially when you're splurging. 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's there to see and do in Windsor?
Take in some sights and attractions while you're in Windsor by visiting Harpoon Brewery, Mt Ascutney State Park and Connecticut River. If you have spare time during your trip, you might want to make a stop at American Precision Museum and Brownsville Trail.
How can I get around Windsor?
It's easier to get around town comfortably when you know your options. To see more of the larger area, hop aboard a train at Windsor Station.

Explore a world of travel with Expedia