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

4 Star Hotels in Windsor CA $189

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Check availability on Windsor 4 Star Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

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 CA $460
CA $567 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 CA $172
CA $189 total
includes taxes & fees
Nov 3 - Nov 4
The Jackson
A spacious living room with a high ceiling, a fireplace, and a large dining table.

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 CA $308
CA $334 total
includes taxes & fees
Nov 22 - Nov 23
Hanover Inn Dartmouth
A large estate with a main building surrounded by a well-maintained lawn and a river.

4. On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.2 out of 10, Wonderful, (1,000 reviews)
"Great place would stay again"
United States
Joseph
The price is CA $228
CA $279 total
includes taxes & fees
Nov 22 - Nov 23
On The River Inn
A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.

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 CA $275
CA $351 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
An outdoor patio with tables and chairs, surrounded by lush greenery and string lights.

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!
An indoor swimming pool with a hot tub, steps leading to the pool, and a reception area with 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 modern house with a covered porch, large windows, and a stone pathway.

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 spacious kitchen with wooden cabinets, a stainless steel refrigerator, and a large island.

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 rural property with a large house surrounded by dense forest, a paved driveway, and a view of rolling hills in the background.

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!
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Learn more about Windsor

Step back in time at the American Precision Museum, where industrial history comes alive through fascinating exhibits. Afterward, savour 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
"Great place would stay again"
Joseph 2-night trip
Posted 5 days ago
On The River Inn

Find out more about Windsor

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Windsor are calling your name. Known for providing first-rate service in amazing locations, each of the Windsor 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Windsor. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Windsor, Vermont, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Windsor hotels with 4 Stars provide everything you need to unwind in style.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Windsor?
We can help you quickly locate the perfect 4-star hotel for your stay in Windsor. Use our handy filter tool to fine-tune your search by things like price, conveniences and star rating and get access to awesome deals in a couple of clicks.

  • Search for the lowest price from CA $189

What's the difference between 5-star and 4-star hotels in Windsor?
If you choose to spend your vacation at a 4-star hotel in Windsor, you'll typically find loads of conveniences to ensure you're relaxed, such as a pool, restaurant and gym. You can look forward to top-quality service and upmarket accommodations. Choose a 5-star hotel and you'll have access to a few more bells and whistles — think on-site spas, 24-hour front desk and opulent turndown services. You're likely to get more amenities and exclusive services at a 5-star getaway, though both are great options for luxury travellers.
Does Windsor have any 4-star all-inclusive resorts?
Enjoy a relaxing vacation experience where everything is included in the one upfront rate by using our "All inclusive" filter. Keeping to your budget is simple when your room, meals and many activities are already taken care of. Eager for more options? Check out the incredible offers on Expedia's standard 4-star resorts in and around Windsor.

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