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

Find 4 Star Hotels in Windsor, VT from $273

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Check availability on Windsor 4 Star Hotels

Tonight
Sep 28 - Sep 29
Tomorrow
Sep 29 - Sep 30
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Windsor 4-star hotels

A room with a checkered floor, a bench, and a fireplace.
A spacious living room with a grand chandelier, large windows, and a comfortable seating area.
A rustic dining area with wooden beams, a chandelier, and a kitchen in the background.
A spacious room with large windows, a fireplace, and comfortable seating areas.

1. Woodstock Inn & Resort

Woodstock Inn & Resort
Woodstock
United States
Ann
$709 nightly
$780 total
Oct 27 - Oct 28
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.
A two-story house with a porch, American flags, and a well-maintained garden.
A well-maintained lawn with a central garden area, a brick building, and a view of a forested hill.
A bedroom with a large window, a bed, a chair, and a lamp.

2. The Jackson

The Jackson
West Woodstock
United States
Laura
$248 nightly
$273 total
Oct 26 - Oct 27
Total with taxes and fees
The Jackson
A hotel lobby with a fireplace, seating areas, and large arched windows.
A spacious living room with a high ceiling, a fireplace, and a large dining table.
A conference room with a fireplace, large windows, and a view of the outdoors.
A conference room with a fireplace, large windows, and a view of the outdoors.

3. Hanover Inn Dartmouth

Hanover Inn Dartmouth
Hanover
United States
Laly
$359 nightly
$390 total
Sep 29 - Sep 30
Total with taxes and fees
Hanover Inn Dartmouth
A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.
A two-story house with a snow-covered roof and a front porch.
A kitchen with white tiled backsplash, wooden crates, and hanging pendant lights.
A spacious living room with a large American flag, a fireplace, and a chandelier.

4. On The River Inn

On The River Inn
West Woodstock
United Kingdom
Laura
$257 nightly
$283 total
Oct 27 - Oct 28
Total with taxes and fees
On The River Inn
A rustic dining area with wooden beams, tables, chairs, and a fireplace.
An outdoor event space with tables set for dining, surrounded by a covered area with a transparent roof.
A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.
A bedroom with a large bed, a bedside table, a lamp, and a view of the outdoors through a sliding door.

5. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
$255 nightly
$278 total
Oct 26 - Oct 27
Total with taxes and fees
The Inn at Weathersfield
A multi-story residential building with a central courtyard.
A living room with a high arched window, a fireplace, a television, and a bookshelf.
A private property entrance with a sign indicating it is for residents and guests only, with a speed limit sign of 15 mph.
An indoor swimming pool with clear water, surrounded by green chairs and large windows offering views of trees.

6. Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property
Clock Tower Base Area
United States
Kathia
Winterplace at Okemo, A Vail Resorts Property
A large, multi-story building with a symmetrical facade, surrounded by a well-maintained lawn and wildflowers.
A dining area with a wooden table, chairs, and a chandelier. There is a window with blinds, a plant, and a view of the outside.
A dining area with a long wooden table, wooden chairs, and a decorative centerpiece.
A kitchen with wooden cabinets, a stainless steel refrigerator, a large island with stools, and a window with decorative curtains.

7. Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts
Clock Tower Base Area
United States
DIEN
Solitude Village at Okemo by Vail Resorts
A man serving drinks at an outdoor table with a white tablecloth, surrounded by guests.
A large, two-story house with a snow-covered roof and a porch with string lights.
A bar area with a wooden counter, various bottles, glasses, and a menu.
A room with a fireplace, a table with a teapot and cup, and a mirror above the fireplace.

8. The Village Inn of Woodstock

The Village Inn of Woodstock
Woodstock
United States
Sam
The Village Inn of Woodstock
A restaurant with a high ceiling and skylights, featuring a bar area with stools and a seating area with tables and chairs.
An indoor swimming pool with a hot tub, steps leading to the pool, and a reception area with chairs.
A modern living room with a large sliding glass door leading to a balcony with a mountain view.
A modern living room with a sofa, coffee table, and fireplace.

9. Mountain Green Resort

Mountain Green Resort
Killington
United States
Jing
Mountain Green Resort
A white building with green shutters, a brick chimney, and a picket fence.
A bedroom with a wooden ceiling, a large bed, a rocking chair, and a sofa.
A wooden table with a stack of magazines and a vase with pink flowers.
Two wooden chairs with red cushions on a porch with a striped rug, a small wooden table, and a view of trees and a white fence in the background.

10. The Woodstocker B&B

The Woodstocker B&B
Woodstock
United States
Kavina
The Woodstocker B&B
A large, multi-story house with a symmetrical roofline, a central staircase, and a well-maintained lawn.
A swimming pool with lounge chairs and tables, surrounded by trees and a stone wall.
An aerial view of a residential property with a tennis court, swimming pool, and multiple houses.
A gym with various exercise machines, wooden walls, and a large mirror.

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

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
Cavendish
United States
Nipa
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
Interior
Interior
Interior
A living room with a grey sofa, a grey armchair, and a coffee table. There is a wooden clock on the wall and a framed picture on the wall.

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

Bright Condo w/ Community Perks: Near Ski Quechee!
Quechee
United States
James
Bright Condo w/ Community Perks: Near Ski Quechee!
A lodge with a dock, a pond, and a grassy area.
A dining area with a wooden table, chairs, and a view of trees through large windows.
A living room with a brown leather sofa, patterned cushions, a wooden coffee table, and a lamp. There are framed posters on the wall and a staircase leading to an upper level.
A spacious living room with a fireplace, a television, and a kitchen in the background.

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

Killington Condo w/ Spa ~ 3 Miles to Ski Resort!
The Woods
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.
An outdoor seating area with a long wooden table and benches, illuminated by string lights forming a triangular pattern.
A wooden play structure and a charging station with cables, set against a snowy background.
A modern living room with a stone wall, a fireplace, a mounted deer head, and a cozy seating area.

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
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.
A spacious living room with a brown leather sofa, a white armchair, and a coffee table with a vase of flowers. A flat-screen TV is mounted on the wall, and there are large windows providing natural light.
A bedroom with a wooden bed, a white wall, and a wooden radiator.
A bathroom with a wooden vanity, a large mirror, a wooden bowl sink, and toiletries on the counter.

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

All-season Ludlow Apartment: 3 Mi to Okemo Resort!
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.
A modern living room with a stone wall, a fireplace, a mounted deer head, and a cozy seating area.
A wooden play structure and a charging station with cables, set against a snowy background.
A modern, A-frame lodge with a stone exterior, large windows, and a covered front porch.

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
Killington
The Birch Ridge: European Room #8 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
A spacious loft-style living area with a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.
A modern living room with a stone wall, a fireplace, a mounted deer head, and a cozy seating area.
An outdoor seating area with a long wooden table and benches, illuminated by string lights forming a triangular pattern.
A modern loft-style interior with a herringbone-patterned wooden floor, a yellow sofa, a bar area with stools, and a stone accent wall.

17. 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
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.
An outdoor seating area with a long wooden table and benches, illuminated by string lights forming a triangular pattern.
A wooden play structure and a charging station with cables, set against a snowy background.
A modern living room with a stone wall, a fireplace, and a mounted deer head.

18. 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
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 a high ceiling, exposed wooden beams, and large windows offering a view of the outdoors.
An outdoor seating area with a long wooden table and benches, illuminated by string lights forming a triangular pattern.
A modern, A-frame lodge with a stone exterior, large windows, and a covered front porch.
A wooden play structure and a charging station with cables, set against a snowy background.

19. The Birch Ridge: English Gentleman's Room #9 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home

The Birch Ridge: English Gentleman's Room #9 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
Killington
The Birch Ridge: English Gentleman's Room #9 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
A spacious loft-style living area with high ceilings, exposed wooden beams, and large windows offering a view of the outdoors.
An outdoor seating area with a long wooden table and benches, illuminated by string lights forming a triangular pattern.
A wooden play structure and a charging station with cables, set against a snowy background.
A modern living room with a stone wall, a fireplace, and a mounted deer head.

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
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

The Jackson

The Jackson

10/10 Excellent
"Garden and grounds out back were very nice. Restaurant provided great dinner and breakfast."
Rick 2-night trip
Posted 1 day ago
The Jackson
On The River Inn

On The River Inn

8/10 Good
"Extremely quaint and love the rooms and balcony… Dining room gorgeous Wish there were Apps on the Tv for streaming… that’s all"
Marcia 2-night trip
Posted 10 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.
  • Search for the lowest price from $273
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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