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

Search Windsor hotels

  • 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 prices for these dates

Tonight
17 Aug - 18 Aug
Tomorrow
18 Aug - 19 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Filter by

Property class

Guest rating

Our top choices for Windsor hotels

1. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Russell
NZ$285
includes taxes & fees
20 Aug - 21 Aug
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

2. Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon
West Lebanon
United States
Jesse
NZ$291
includes taxes & fees
6 Sept - 7 Sept
Fireside Inn & Suites West Lebanon

3. Align Inn Vermont

Align Inn Vermont
Quechee
United States
Tammy
NZ$196
includes taxes & fees
24 Aug - 25 Aug
Align Inn Vermont

4. On The River Inn

On The River Inn
West Woodstock
United Kingdom
Laura
NZ$503
includes taxes & fees
7 Sept - 8 Sept
On The River Inn

5. Claremont Motor Lodge

Claremont Motor Lodge
Claremont
United States
Shane
NZ$193
includes taxes & fees
25 Aug - 26 Aug
Claremont Motor Lodge

6. The Mountain Inn at Killington

The Mountain Inn at Killington
Killington
United States
Travis
NZ$245
includes taxes & fees
18 Aug - 19 Aug
The Mountain Inn at Killington

7. Woodstock Inn & Resort

Woodstock Inn & Resort
Woodstock
United States
ben
NZ$838
includes taxes & fees
7 Sept - 8 Sept
Woodstock Inn & Resort

8. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Denis
NZ$247
includes taxes & fees
7 Sept - 8 Sept
The Common Man Inn & Restaurant

9. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
Killington
United States
Holaiza
NZ$259
includes taxes & fees
30 Aug - 31 Aug
Killington Mountain Lodge, Tapestry Collection by Hilton

10. Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG
White River Junction
United States
Rena
NZ$269
includes taxes & fees
14 Sept - 15 Sept
Holiday Inn Express Hotel & Suites White River Junction by IHG

11. Mountain Meadows Lodge

Mountain Meadows Lodge
Killington
United States
Barry
NZ$345
includes taxes & fees
18 Aug - 19 Aug
Mountain Meadows Lodge

12. The Shire Woodstock

The Shire Woodstock
Woodstock
United States
mary
NZ$425
includes taxes & fees
20 Aug - 21 Aug
The Shire Woodstock

13. Kedron Valley Inn

Kedron Valley Inn
South Woodstock
United States
Kathryn
NZ$610
includes taxes & fees
18 Aug - 19 Aug
Kedron Valley Inn

14. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Stephen
NZ$261
includes taxes & fees
18 Aug - 19 Aug
Pointe at Castle Hill Resort

15. Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon
Lebanon
United States
Deborah
NZ$300
includes taxes & fees
6 Sept - 7 Sept
Hilton Garden Inn Hanover Lebanon

16. The Jackson

The Jackson
West Woodstock
United States
Brian
NZ$301
includes taxes & fees
25 Aug - 26 Aug
The Jackson

17. Hotel Coolidge

Hotel Coolidge
White River Junction
United States
Nancy
NZ$246
includes taxes & fees
26 Aug - 27 Aug
Hotel Coolidge

18. The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm
Quechee
United States
Ken
NZ$301
includes taxes & fees
1 Sept - 2 Sept
The Quechee Inn at Marshland Farm

19. Six South St Hotel

Six South St Hotel
Hanover
United States
Tamzen
NZ$425
includes taxes & fees
6 Sept - 7 Sept
Six South St Hotel

20. Hanover Inn Dartmouth

Hanover Inn Dartmouth
Hanover
United States
Laly
NZ$608
includes taxes & fees
13 Sept - 14 Sept
Hanover Inn Dartmouth
View all properties
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Windsor attractions

Brownsville Trail

9.4/10 (3 reviews)
This challenging 5.2-mile trail rewards hikers with panoramic views and the historic Norcross Quarry from the early 1900s. Pack water and wear sturdy boots for the 2,395-foot ascent through Vermont's forests.
See properties

Harpoon Brewery

9.4/10 (23 reviews)
This working brewery offers a unique tasting experience with fresh craft beers and handmade pretzels. Enjoy the communal atmosphere in the taproom overlooking brewing operations or relax in the outdoor beer garden.
See properties

American Precision Museum

10.0/10 (2 reviews)
Housed in the historic 1846 Robbins & Lawrence Armoury, this museum showcases America's largest collection of significant machine tools. Interactive exhibits highlight how precision manufacturing shaped our industrial heritage.
See properties

Weathersfield Proctor Library

This community-centered library offers a welcoming hub for book lovers and local engagement. Browse their diverse collection or join one of their regular educational programs in this Ascutney gathering place.
See properties

Ascutney Park

Vermont's first state park offers 12+ miles of trails through former quarries and historic homesteads. Drive the 3.7-mile auto road for panoramic views of the Connecticut River Valley without the summit hike.
See properties

Windsor Public Library

This historic library has served as Windsor's community hub since 1882, offering diverse collections for all ages. Browse books, use free Wi-Fi, or join one of their engaging programs.
See properties

Mount Ascutney Hospital

If Mount Ascutney Hospital is what brings you to town, hopefully you'll have a chance to explore more of Windsor.
See properties

Silo Distillery

You can take time to visit Silo Distillery during your travels to Windsor. Wander the forests or discover the area's mountain views.
See properties

Learn more about Windsor

Step back in time at the American Precision Museum, where industrial history comes alive through fascinating exhibits. Afterwards, 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

Recent Reviews in Windsor

The Shire Woodstock

The Shire Woodstock

8/10 Good
"We stayed in the River House and had two different rooms as we stayed one night each at the beginning and end of a longer trip to Canada. Both rooms were very clean. One room had a better view of the river than the other. There is construction occurring at the property and we weren’t made aware of it ahead of time so the sawing and drilling made sitting by the river and relaxing a little difficult. The whole property is getting a face lift. The outdoor space was lovely with chairs and fire pits. The location is great. Grocery store across the street and walkable to breakfast and shops. Would recommend but make sure you check about construction and confirm a good view of the river if that is important to you."
Jessica 1-night trip
Posted 3 hours ago
The Shire Woodstock
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

10/10 Excellent
"."
Don 3-night trip
Posted 8 hours ago
Fireside Inn & Suites West Lebanon
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Laundry room in the building, get beds."
Gene 4-night trip
Posted 22 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"I spent 2 nights a this beautiful place and loved it. Since the moment we checked in and out we had a great time. The room was very clean, the beds were very comfortable and the view of the mountains at the hot tub was stunning."
Holaiza 2-night trip
Posted 1 day ago
Killington Mountain Lodge, Tapestry Collection by Hilton
The Mountain Inn at Killington

The Mountain Inn at Killington

8/10 Good
"Everything was good we enjoyed the stay for the weekend."
Trisha 2-night trip
Posted 1 day ago
The Mountain Inn at Killington
Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

8/10 Good
"Great stay"
Rena 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites White River Junction by IHG
Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

8/10 Good
"Easy check in and out with no visible staff seen. Pool water was cold but the grounds were nice."
Michael 1-night trip
Posted 2 days ago
Hideaway Inn Mt.Sunapee
Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"Great place, we stopped for a few days while taking a break from hiking the AT. The grounds are amazing, breakfast was delicious, and staff was very accommodating. They even washing our stinky hiking clothes and picked up a pizza for us. Would highly recommend!"
Matthew 1-night trip
Posted 4 days ago
Mountain Meadows Lodge
Hotel Coolidge

Hotel Coolidge

10/10 Excellent
"Here's the thing about the Coolidge. Its old. They don't hide that. However, the rooms are clean, the staff is nice, you can walk to dinner and sweet art galleries. I was very happy with my stay. If you like sterile hotels this isn't the place for you. If you like hotels with some character and fantastic staff definitely give it a try!"
Jennifer 2-night trip
Posted 6 days ago
Hotel Coolidge

More cheap accommodation in Windsor

Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction

442 North Hartland Rd White River Junction VT
NZ$168
23 Aug - 24 Aug
includes taxes & fees
6.2/10 (1,022 reviews)
Super 8 by Wyndham White River Junction
Align Inn Vermont

Align Inn Vermont

5817 Woodstock Rd Quechee VT
NZ$196
24 Aug - 25 Aug
includes taxes & fees
Align Inn Vermont
The Mountain Inn at Killington

The Mountain Inn at Killington

47 Old Mill Rd Killington VT
NZ$245
18 Aug - 19 Aug
includes taxes & fees
9.2/10 Wonderful! (1,020 reviews)
The Mountain Inn at Killington
Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

121 Ballardvale Dr White River Junction VT
NZ$269
14 Sept - 15 Sept
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
Holiday Inn Express Hotel & Suites White River Junction by IHG
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

25 Airport Road West Lebanon NH
NZ$291
6 Sept - 7 Sept
includes taxes & fees
8.4/10 Very good! (1,008 reviews)
Fireside Inn & Suites West Lebanon
Six South St Hotel

Six South St Hotel

6 South Street Hanover NH
NZ$425
6 Sept - 7 Sept
includes taxes & fees
Six South St Hotel

Find out more about Windsor

Top reasons to visit Windsor

  • Outdoor Adventures: Windsor is a haven for outdoor enthusiasts, offering skiing, scenic parks, and various activities amidst stunning landscapes.
  • Cultural Experiences: Visitors can immerse themselves in local history and charm at attractions like Windsor Great Park and the farmers market.
  • Family-Friendly Activities: Enjoy engaging experiences suitable for all ages, ensuring a fun-filled holiday for families.
  • Charming Accommodations: Windsor boasts delightful stays, from agritourism to inviting hotels, catering to diverse traveller needs.
  • Picturesque Surroundings: The scenic beauty of Windsor provides a perfect backdrop for relaxation and exploration.

Find great hotels near Windsor

Discover a delightful selection of accommodations in Windsor, Vermont, perfect for every type of traveller. From charming agritourism properties to inviting hotels, you'll find options that cater to adventure seekers, families, and pet owners alike. Whether you're considering a stay at the Inn at Windsor or the Windsor Mansion Inn, you're sure to enjoy a memorable experience in this picturesque town.

  • Best Western West Lebanon-Hanover Hotel: The Best Western West Lebanon-Hanover Hotel offers a welcoming atmosphere for families and business travellers alike. With a commendable guest rating of 8.4 out of 10, this budget-friendly lodging is located 17.7km from Windsor. Families will find excellent amenities tailored for children, including complimentary cribs. The hotel features comfortable rooms designed for relaxation after a day of exploring the area. Guests appreciate its convenient location and friendly service, making it a solid choice for your stay.
  • Fireside Inn & Suites West Lebanon: Fireside Inn & Suites West Lebanon is a charming pet-friendly accommodation with a guest rating of 8.2 out of 10. Situated 17.7km from Windsor, this hotel is an excellent option for those travelling with furry companions. The property allows pets on-site, with amenities that include food and water bowls, and a no-fee policy for service animals. Designed for both leisure and business travellers, the Fireside Inn boasts a cosy atmosphere that promises a warm welcome after a day of adventures.
  • Holiday Inn Express Hotel & Suites White River Junction by IHG: With a guest rating of 8.6 out of 10, the Holiday Inn Express Hotel & Suites White River Junction by IHG stands out as an ideal choice for business travellers. Located 19.3km from Windsor, this budget-friendly hotel combines modern comfort with practical amenities. Guests can enjoy complimentary breakfast and high-speed internet access, ensuring a productive stay. The hotel’s sleek design and attentive service create an inviting environment for those visiting the area on business.

Where to stay near Windsor

Windsor, Vermont, offers a delightful mix of outdoor adventures and serene getaways, perfect for travellers seeking both excitement and relaxation. Explore the picturesque scenery and family-friendly atmosphere, or immerse yourself in the rich history of the area. Nearby cities provide a vibrant urban vibe, ensuring a memorable weekend escape. Whether you’re hitting the slopes or enjoying leisurely excursions, Windsor promises an unforgettable experience for every kind of visitor.

  • Woodstock: Nestled 19.3km from Windsor, Woodstock is a charming town renowned for its stunning landscapes and outdoor adventures. Travellers flock here year-round, with peaks in visitor numbers during July and the autumn months of September to October. This picturesque spot is perfect for skiing enthusiasts, offering access to ski fields and resorts. Beyond winter sports, Woodstock boasts nearby lakes and mountains, making it an ideal base for hiking and exploring the scenic beauty of national and state parks. Don't miss the local shops and eateries that contribute to the town's vibrant atmosphere.
  • West Lebanon: Also located 19.3km from Windsor, West Lebanon is a lively city that attracts visitors throughout the year, particularly in June to July and September. Known for its adventurous spirit, the city offers ample opportunities for skiing and outdoor activities. With its proximity to historic colleges and universities, West Lebanon combines education with adventure. Explore the stunning natural landscapes, including lakes and mountains, while enjoying the various ski fields in the area. This city is perfect for those seeking both thrills and a touch of culture.
  • White River Junction: Situated 19.3km from Windsor, White River Junction is a vibrant city that offers a mix of adventure and historical charm. Visitors are drawn to its ski fields and resorts, especially during the summer months of July to September. The town is not only a hub for outdoor activities but also home to historic colleges and universities. Explore the nearby lakes and the dramatic canyon gorge, which provide breathtaking views and ample recreational opportunities. White River Junction is a fantastic destination for those looking to immerse themselves in nature and history alike.

Things to do in Windsor

Shopping

In the heart of Windsor, you can explore charming local shops for unique gifts. If you're up for a drive, consider visiting the nearby West Lebanon Shopping Plaza, where you'll find larger retailers and a diverse selection of souvenirs to take home.

Recreation

In Windsor, the Salt Spa provides a serene environment with salt therapy sessions that promote relaxation and respiratory health. For outdoor enthusiasts, the nearby Mount Ascutney offers hiking trails with stunning views, ideal for connecting with nature while enjoying physical activity.

Adventure

In Windsor, explore the scenic beauty of the Connecticut River by kayaking or canoeing, offering a unique perspective of the landscape. For thrill-seekers, nearby hiking trails present challenging terrains and breathtaking views, ideal for an adventurous day out in nature.

Nightlife

In Windsor, the Harpoon Brewery offers a relaxed vibe with craft beers and occasional live music, while the Windsor Station is a charming spot for casual dining and drinks. The local taverns often host trivia nights and pub games, adding a fun twist to your evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Windsor

Windsor, Vermont, offers a fantastic blend of outdoor adventures and cultural experiences, making it a perfect destination for tourists. You can explore stunning attractions like canyonGorge and the nationalStatePark, or enjoy family-friendly activities at the historic Windsor Great Park and the local farmers market. Don’t miss out on the main attractions that showcase the charm and beauty of Windsor, ensuring a memorable visit.

  • Blow-Me-Down Bridge: This historic bridge, located 805m from Windsor, offers a picturesque glimpse into the region’s architectural heritage. Its unique design and serene surroundings create a tranquil atmosphere, ideal for photography and leisurely strolls.
  • Taftsville Covered Bridge: Situated 17.7km from Windsor, this charming covered bridge exudes historical charm. With its rich history and scenic backdrop, it's a lovely spot for exploring local culture and enjoying a peaceful picnic by the river.
  • American Precision Museum: Located within Windsor, this museum showcases the evolution of precision manufacturing. Visitors will appreciate the fascinating exhibits and insights into the region’s industrial heritage, making for an enlightening experience.

Best time to go to Windsor

The best time to visit Windsor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windsor falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Windsor falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January16.7°F (-8.5°C)Light RainMostly CloudyAverageSlightly High
February18.9°F (-7.3°C)Light RainMostly CloudySlightly LowSlightly High
March27.1°F (-2.7°C)Light RainMostly CloudyAverageAverage
April39.4°F (4.1°C)Light RainMostly CloudyAverageSlightly Low
May52.3°F (11.3°C)Light RainMostly SunnySlightly LowSlightly Low
June59.9°F (15.5°C)Light RainMostly SunnyAverageAverage
July65.8°F (18.8°C)Light RainMostly SunnySlightly HighAverage
August64.0°F (17.8°C)Light RainMostly SunnySlightly HighAverage
September57.0°F (13.9°C)Light RainMostly SunnySlightly HighAverage
October45.5°F (7.5°C)Light RainMostly CloudyAverageSlightly High
November33.1°F (0.6°C)Light RainMostly SunnyAverageSlightly Low
December24.3°F (-4.3°C)Light RainMostly CloudySlightly LowAverage

The nearest major airports for your trip to Windsor

Visiting Windsor, Vermont, is easy with access to several major airports. Burlington International Airport (BTV) is 125.5km away, with nearby hotels like the DoubleTree by Hilton Burlington, just 3.2km from the airport, offering convenient transportation options. Albany International Airport (ALB) is located 141.6km from Windsor, with excellent accommodation such as The Landing Hotel at Rivers Casino & Resort, 12.9km away. Manchester-Boston Regional Airport (MHT) is 98.2km from Windsor, with luxurious options like The Grand at Bedford Village Inn, situated 6.4km from the airport. Each airport provides accessible transport to their respective hotels, ensuring a smooth journey for tourists.

Frequently asked questions

What is the best area to stay in Windsor?
The best area to stay in Windsor, Vermont, is the downtown historic district, particularly around Main Street and State Street.This area is the heart of Windsor, offering a convenient and pleasant base for exploring. It's very walkable, with historic brick buildings housing local shops, eateries, and a brewery. The American Precision Museum is a prominent landmark here, and the district is close to the Cornish-Windsor Covered Bridge, a well-known local attraction.Couples looking for a relaxing getaway will find this area particularly appealing. You can enjoy strolls along the Connecticut River, explore the quaint shops, and dine at local restaurants, all within easy reach. Many of the accommodations in this district offer a charming, historic feel, great for a romantic escape.Travellers interested in history and local culture will also appreciate staying downtown. Being within walking distance of the American Precision Museum and the historic covered bridge allows for easy exploration of Windsor's significant past and engineering heritage.
What are the best family hotels in Windsor?
For families visiting Windsor, Fat Sheep Farm & Cabins is an excellent choice.This 3-star property, with an outstanding 9.8 rating, offers a wonderful experience for families. Guests appreciate the free cribs, free toiletries, and complimentary WiFi. Each cabin includes a full kitchen, which is very convenient for families. The property also provides free parking for RVs, buses, and trucks, as well as an electric car charging station and accessible parking options.
What are the top pet-friendly hotels in Windsor?
For top pet-friendly accommodation in Windsor, Fat Sheep Farm & Cabins is an excellent choice.This 3-star property, with an outstanding 9.8 rating, warmly welcomes both dogs and cats, ensuring they have food and water bowls provided. Guests appreciate the convenience of complimentary self-parking and free RV, bus, or truck parking. For those travelling with infants, a free crib is available, and all guests benefit from free WiFi and complimentary toiletries.
What are the best budget hotels in Windsor?
For a highly-rated budget hotel in Windsor, Vermont, consider the Fat Sheep Farm & Cabins.The 3-star Fat Sheep Farm & Cabins, with an exceptional 9.8 rating, offers excellent value. Guests can enjoy convenient amenities such as free self-parking, complimentary toiletries, and free WiFi. The cabins also feature a kitchen, which is ideal for those who prefer to prepare their own meals. Additionally, it provides free cots, free RV, bus, and truck parking, and an electric car charging station.
What are the most romantic hotels in Windsor for couples?
For a romantic getaway in Windsor, couples should consider the Fat Sheep Farm & Cabins.This 3-star property, with an outstanding 9.8 rating, is often highlighted for its beautiful mountain views, providing a delightful backdrop for a couple's retreat. Guests appreciate the convenience of free parking and complimentary WiFi. Each cabin includes a kitchen, offering the flexibility for private dining experiences.
When is the best time to go to Windsor?
The best time to visit Windsor, Vermont, is during late spring, summer, and autumn, from May to October, when the weather is most pleasant for outdoor activities.Late spring and early summer, particularly May and June, offer mild temperatures and lush green landscapes. This is a lovely time for exploring the outdoors, with opportunities for hiking and enjoying the Connecticut River. The crowds are typically smaller during these months, making for a more relaxed visit.Summer, from July to August, brings warmer weather, ideal for water activities on the Connecticut River, such as kayaking or paddleboarding. Many local farms are open for visits, and there are often community events and farmers' markets in the area. This is a popular time for families due to school holidays.Autumn, especially September and October, is particularly stunning due to the vibrant fall foliage. The scenic drives along Route 5 and other local roads are breathtaking. This period is superb for leisurely drives, photography, and enjoying the crisp New England air.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to 'My Trips' and selecting your reservation. To find flexible deals, filter your search by 'Fully refundable property' for hotels in Windsor.
How can I save on a hotel booking in Windsor with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Windsor hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Windsor?
Prices for hotels in Windsor often vary, but you can find a great deal from NZ$168 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by 'Price: low to high' for our cheapest rates.

Explore a world of travel with Expedia