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

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Our top choices for Windsor 4-star hotels

Breakfast, lunch, dinner and brunch served

Hanover Inn Dartmouth

Hanover Inn Dartmouth
4.0 star property
Hanover
9.6 out of 10, Exceptional, (962 reviews)
"Excellent place to stay right by Dartmouth. Great location and the staff is incredibly friendly and helpful."
United States
Kyle
$369 nightly
The price is $400
Jul 22 - Jul 23
Total with taxes and fees
Hanover Inn Dartmouth
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (296 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
$179 nightly
The price is $197
Jul 28 - Jul 29
Total with taxes and fees
The Jackson
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,000 reviews)
"convenient location with very comfortable accommodations"
United States
Tonine
$239 nightly
The price is $263
Jul 26 - Jul 27
Total with taxes and fees
On The River Inn
Interior

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (80 reviews)
"Great location, service and restaurant "
United States
LUDJANE
$225 nightly
The price is $245
Jul 20 - Jul 21
Total with taxes and fees
The Inn at Weathersfield
Terrace/patio

The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (99 reviews)
"Inn was beautiful, the details exactly what you'd want for a weekend getaway. Room was cozy (room 6), bed was comfortable, jetted tub was awesome for us not having a tub at home, bar was a nice place to hang out and breakfast was excellent. Location was perfect, it was an easy walk into the center of town, even in winter. Honestly, nothing bad to say."
United States
Nicholas
The Village Inn of Woodstock
Exterior

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, (35 reviews)
"Great location!"
United States
DIEN
Solitude Village at Okemo by Vail Resorts
Exterior

The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (51 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
Property grounds

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, (26 reviews)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
United States
Kathia
Winterplace at Okemo, A Vail Resorts Property
Restaurant

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
Apartment (3 Bedrooms) | Interior

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!
Cottage, 1 Bedroom | Interior

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
$1,899 nightly
The price is $2,089
Jul 26 - Jul 27
Total with taxes and fees
The Birch Ridge: Owner's Suite #5 - Queen/sofa Bed Suite In Killington. Hot Tub. Renovated. 1 Bedroom Home
Apartment (3 Bedrooms) | Interior

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!
Apartment (2 Bedrooms) | Interior

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!
Apartment (2 Bedrooms) | Interior

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!
Cottage, 1 Bedroom | Living area

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
$1,480 nightly
The price is $1,628
Jul 26 - Jul 27
Total with taxes and fees
The Birch Ridge: European Room #8 - King Suite In Killington, Vermont. Hot Tub. 1 Bedroom Home
Cottage, 1 Bedroom | Living area

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
$1,381 nightly
The price is $1,519
Jul 26 - Jul 27
Total with taxes and fees
The Birch Ridge: Family Room #11 - Queen/bunkbed Suite In Killington, Vermont 1 Bedroom Home
Apartment (4 Bedrooms) | Interior

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!
Cottage, 1 Bedroom | Interior

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
$1,258 nightly
The price is $1,384
Jul 26 - Jul 27
Total with taxes and fees
The Birch Ridge: Colonial Maple Room #1 - Queen Suite In Renovated Killington Lodge 1 Bedroom Home
Apartment (3 Bedrooms) | Interior

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!
Signature House, Multiple Beds, Patio, Lake View | Desk, laptop workspace, WiFi (free), individually decorated

Valhalla

Valhalla
4.0 star property
Sunapee
Valhalla
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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
"Everything was terrific! Great vibe & location."
Brian 1-night trip
Posted 5 days ago
The Jackson
On The River Inn

On The River Inn

10/10 Excellent
"Great hotel! Our room was spacious and we loved having a full size fridge and mini-kitchen. Insanely loved the bath products (sorry, I love that kind of thing!). We had a great dinner at the restaurant which has a wonderful vibe and friendly staff. When we checked in, the front desk staff forgot to mention breakfast was included (clearly I had forgotten, too)-- took me 2 days to realize that! Breakfast was great. Another plus-- the gigantic backyard/meadow adjacent to the river is stunning and smores at night were an added bonus! They do a great job creating a hotel that is perfect for families, mountain bike travelers, horse show folks, couples getaways. Hard for one place to cover all that. I had booked via an online site which I thought included all fees but there was a small daily added cost. Overall though our total expenditure was LESS than other area hotels and really, this was so beautiful, immaculate, delish and otherwise very hospitable! We will be back!"
Audra Michael 3-night trip
Posted 7 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 $197

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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