A snow-covered river valley with a bridge and a town.

Windsor 4 Stars Hotels

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Windsor 4 Star Hotels

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15

Our top choices for Windsor 4-star hotels

A room with a checkered floor, a bench, and a fireplace.

1. Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (628 reviews)
"Absolutely beautiful hotel and property, which is a destination just in and of itself. Very comfortable, great dining options, gorgeous spa, and very walkable, if you decide to wander; Woodstock is a town right out of a Hallmark movie, after all."
United States
Darrah
The price is NT$10,725
NT$13,232 total
includes taxes & fees
Nov 30 - Dec 1
Woodstock Inn & Resort
A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

2. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (337 reviews)
"Amazing stay and great restaurant!"
United States
Ava
The price is NT$4,016
NT$4,418 total
includes taxes & fees
Nov 15 - Nov 16
The Jackson
A hotel lobby with a fireplace, seating areas, and large arched windows.

3. Hanover Inn Dartmouth

Hanover Inn Dartmouth
4.0 star property
Hanover
9.6 out of 10, Exceptional, (989 reviews)
"Everything was great"
United States
Mark
The price is NT$7,168
NT$7,777 total
includes taxes & fees
Nov 22 - Nov 23
Hanover Inn Dartmouth
A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.

4. On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.2 out of 10, Wonderful, (1,001 reviews)
"Great place would stay again"
United States
Joseph
The price is NT$5,319
NT$6,503 total
includes taxes & fees
Nov 22 - Nov 23
On The River Inn
A rustic dining area with wooden beams, tables, chairs, and a fireplace.

5. The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (83 reviews)
"Such a nice and kind family of owners. Breakfast was delicious, as well as dinner the previous night in their restaurant. It’s a very rustic Inn, full of history and charm. We would love to return in the near future."
United States
Dorrie
The price is NT$6,745
NT$8,552 total
includes taxes & fees
Nov 29 - Nov 30
The Inn at Weathersfield
A multi-story residential building with a central courtyard.

6. Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property
4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (29 reviews)
"Large unit - well laid out for three generation visit. Comfortable beds. Kitchen well appointed."
United States
Lori A.
Winterplace at Okemo, A Vail Resorts Property
A man serving drinks at an outdoor table with a white tablecloth, surrounded by guests.

7. The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (103 reviews)
"Owners were very friendly. Food was incredible. Breakfast is included but they also have dinner available. Both were excellent. It was also nice having a small bar on site. Great place for a few drinks before we went out."
United States
Sam
The Village Inn of Woodstock
A large, multi-story building with a symmetrical facade, surrounded by a well-maintained lawn and wildflowers.

8. Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts
4.0 star property
Clock Tower Base Area
7.8 out of 10, Good, (36 reviews)
"Great location!"
United States
DIEN
Solitude Village at Okemo by Vail Resorts
A large, multi-story house with a snow-covered roof and multiple windows, surrounded by trees.

9. Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
4.0 star property
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful four night stay at this great condo! Perfect if you are skiing out of Okemo! The condo was beautiful, clean and the host Bill was so communicative and responded to texts immediately. The gym and spa was also an added bonus! Great time! "
United States
Nipa
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
A restaurant with a high ceiling and skylights, featuring a bar area with stools and a seating area with tables and chairs.

10. Mountain Green Resort

Mountain Green Resort
4.0 star property
Killington
4.0 out of 10, (2 reviews)
"Clean room, elevator broken and not enough bathroom towels."
United States
Jing
Mountain Green Resort
A white building with green shutters, a brick chimney, and a picket fence.

11. The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (53 reviews)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
United States
Kavina
The Woodstocker B&B
Interior

12. Bright Condo w/ Community Perks: Near Ski Quechee!

Bright Condo w/ Community Perks: Near Ski Quechee!
4.0 star property
Quechee
10.0 out of 10, Exceptional, (1 review)
"Great place for 2 couples to relax and enjoy the fall sights.Only problem was the master bedroom bath. The bathtub drain was blocked and took 30 minutes to drain the water. Property owner was unable to get a plumber over the weekend, so I removed the stopper cleaned a lot of hair and waste, replaced the stopper and bathtub drained real good after that. "
United States
James
Bright Condo w/ Community Perks: Near Ski Quechee!
A lodge with a dock, a pond, and a grassy area.

13. Killington Condo w/ Spa ~ 3 Miles to Ski Resort!

Killington Condo w/ Spa ~ 3 Miles to Ski Resort!
4.0 star property
The Woods
8.0 out of 10, Very good, (1 review)
"Great property and location. Ground floor bedroom very drafty especially when windy at Killington. Made it difficult to comfortably get rest. Otherwise very nice living space. At the high end for cost for the size and location. "
United States
Craig
Killington Condo w/ Spa ~ 3 Miles to Ski Resort!
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.

14. 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
A modern kitchen with wooden cabinets, stainless steel appliances, and a granite countertop.

15. All-season Ludlow Apartment: 3 Mi to Okemo Resort!

All-season Ludlow Apartment: 3 Mi to Okemo Resort!
4.0 star property
Ludlow
All-season Ludlow Apartment: 3 Mi to Okemo Resort!
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.

16. The Birch Ridge: European Room #8 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home

The Birch Ridge: European Room #8 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
4.0 star property
Killington
The Birch Ridge: European Room #8 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
A parking lot with a building in the background, surrounded by greenery and mountains.

17. 1 Mi to Killington Resort: Townhome w/ Dry Sauna!

1 Mi to Killington Resort: Townhome w/ Dry Sauna!
4.0 star property
Killington
1 Mi to Killington Resort: Townhome w/ Dry Sauna!
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.

18. 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
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.

19. 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
A modern living room with a stone fireplace, a flat-screen TV mounted above it, and a large window with curtains.

20. Ski-in/out Townhome w/ Views at Okemo Resort!

Ski-in/out Townhome w/ Views at Okemo Resort!
4.0 star property
Ludlow
Ski-in/out Townhome w/ Views at Okemo Resort!
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Windsor

Step back in time at the American Precision Museum, where industrial history comes alive through fascinating exhibits. Afterward, savor craft brews at Harpoon Brewery or hike the scenic trails of Mt Ascutney State Park for breathtaking views.

See all hotels in Windsor
A covered bridge over a river with lush greenery and a clear sky.

Top Windsor Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"A classy and comforting hotel in a beautiful riverside location. Great pool, sauna, and gym. The staff support was excellent, warm and welcoming."
Mia 1-night trip
Posted 16 hours ago
On The River Inn

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Windsor?
With Expedia's handy search filters, landing a top deal on a 4-star hotel in Windsor just got easier. Start by entering your chosen arrival date and length of your stay. Then sort the results by price and pick the option that best fits your style and budget.

  • Search for the lowest price from NT$4,418

What's the difference between 5-star and 4-star hotels in Windsor?
Treat yourself to refined living during your Windsor getaway by choosing a 4-star hotel. As well as featuring upscale accommodations, these properties are usually packed with amenities like large beds, bathrobes and more. A 5-star hotel will go the extra mile to make your trip an even more indulgent and unforgettable one. Concierge assistance, elegant décor and world-class dining are only the start of the exclusive conveniences and services you'll likely be able to enjoy.
Does Windsor have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to find your dream resort in Windsor where everything is taken care of, from your accommodations to your food, activities and entertainment. We can also help you find standard 4-star stays in and around this sought-after destination.

Explore a world of travel with Expedia