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

4 Star Hotels in Windsor CA $248

  • 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

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
The price is CA $476
CA $516 total
includes taxes & fees
Jul 22 - Jul 23
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
The price is CA $226
CA $248 total
includes taxes & fees
Aug 19 - Aug 20
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
The price is CA $339
CA $404 total
includes taxes & fees
Aug 12 - Aug 13
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
The price is CA $241
CA $314 total
includes taxes & fees
Jul 21 - Jul 22
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
The price is CA $1,883
CA $2,929 total
includes taxes & fees
Jul 26 - Jul 27
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
The price is CA $1,489
CA $2,312 total
includes taxes & fees
Jul 26 - Jul 27
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
The price is CA $1,331
CA $2,151 total
includes taxes & fees
Jul 26 - Jul 27
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
The price is CA $1,226
CA $1,942 total
includes taxes & fees
Jul 26 - Jul 27
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

Valhalla

Valhalla
4.0 star property
Sunapee
Valhalla
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, 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

The Jackson

The Jackson

10/10 Excellent
"Everything was terrific! Great vibe & location."
Brian 1-night trip
Posted 6 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

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 $248

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.

Explore a world of travel with Expedia