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

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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
$369 nightly
The price is $406
Nov 30 - Dec 1
Total with taxes and fees
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
$176 nightly
The price is $194
Nov 3 - Nov 4
Total with taxes and fees
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
$239 nightly
The price is $259
Nov 22 - Nov 23
Total with taxes and fees
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, (1,005 reviews)
"Great place would stay again"
United States
Joseph
$181 nightly
The price is $200
Nov 22 - Nov 23
Total with taxes and fees
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
$227 nightly
The price is $247
Nov 29 - Nov 30
Total with taxes and fees
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 spacious loft-style living area with high ceilings, exposed wooden beams, and large windows offering a view of the outdoors.

20. The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home

The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home
4.0 star property
Killington
The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home
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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, 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
"Great place would stay again"
Joseph 2-night trip
Posted 5 days ago
On The River Inn

Find out more about Windsor

Windsor Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Windsor, Vermont are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Windsor 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Windsor. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Windsor, Vermont, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Windsor hotels offer everything your heart desires.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Windsor?
Expedia can help you easily track down the ideal 4-star hotel for your stay in Windsor. Use our handy filter tool to tailor your search by things like budget, amenities and property star rating and get access to fantastic deals in a couple of clicks.

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What's the difference between 5-star and 4-star hotels in Windsor?
Offering a welcoming guest experience and upscale décor, 4-star hotels are a terrific option for your Windsor escape. These kinds of stays generally come with lots of handy amenities that make it easy to unpack and relax — think large beds, bathrobes, gyms and restaurants. Or live in the lap of luxury at a 5-star hotel designed to spoil you with luxury perks and amenities. Concierge assistance, complimentary toiletries and gourmet dining are typically featured at these plush properties.
Does Windsor have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to search for your dream resort in Windsor where everything is taken care of, from your accommodations to your food, entertainment and activities. We can also help you find standard 4-star stays in and around this much-loved destination.

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