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Find hotels in Windsor, VT from Rp1.322.940

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Our top choices for Windsor hotels

Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (12)
"An absolutely stunning property! The cabin was clean, well stocked and perfectly located to see the gorgeous sunrise. So very grateful for our quick trip at Fat Sheep Farm. Looking forward to returning! "
United States
Jasmine
Fat Sheep Farm & Cabins

Align Inn Vermont

Align Inn Vermont
2.5 star property
Quechee
9.4 out of 10, Exceptional, (1046)
"Overall great stay."
United States
Kathryn
The price is Rp1.872.675
Rp2.060.109 total
includes taxes & fees
13 Jan - 14 Jan 2026
Align Inn Vermont

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (554)
"Highly recommend stay here"
United States
Margie
The price is Rp5.642.994
Rp6.939.718 total
includes taxes & fees
15 Dec - 16 Dec
Woodstock Inn & Resort

Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon
3.0 star property
Lebanon
9.0 out of 10, Wonderful, (1003)
"This hotel is solid. Location relative to Hanover is good, facility is nice, and it’s clean and comfortable. Would definitely stay again. "
United States
Merridith
The price is Rp1.913.237
Rp2.075.862 total
includes taxes & fees
20 Dec - 21 Dec
Hilton Garden Inn Hanover Lebanon

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (549)
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
The price is Rp1.288.400
Rp2.732.274 total
includes taxes & fees
14 Dec - 15 Dec
Sleep Woodstock Motel

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (893)
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock

Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon
2.5 star property
West Lebanon
8.2 out of 10, Very good, (1002)
"Staff was excellent. Everything was clean as expected. "
United States
Robert
The price is Rp2.337.098
Rp2.896.970 total
includes taxes & fees
15 Dec - 16 Dec
Fireside Inn & Suites West Lebanon

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.4 out of 10, Exceptional, (179)
"All round fantastic place to stay "
United Kingdom
Stephen
The price is Rp2.911.385
Rp3.618.674 total
includes taxes & fees
14 Dec - 15 Dec
Mountain Meadows Lodge

Hampton Inn White River Junction

Hampton Inn White River Junction
2.5 star property
White River Junction
8.6 out of 10, Excellent, (1002)
"Room was clean, breakfast was substantial, staff was fine"
United States
Kristi
The price is Rp1.897.311
Rp2.087.042 total
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn White River Junction

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (958)
"Great place to stay!"
United States
Stephen
The price is Rp3.880.183
Rp4.481.769 total
includes taxes & fees
23 Dec - 24 Dec
The Mountain Inn at Killington

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
Killington
7.4 out of 10, Good, (1004)
"Staff was very helpful and room service was great."
United States
Ankita
The price is Rp3.395.784
Rp3.735.362 total
includes taxes & fees
14 Dec - 15 Dec
Killington Mountain Lodge, Tapestry Collection by Hilton

Summit Lodge

Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (396)
"When we first arrived it felt really old and I was wondering what I had booked. Then, the place grew on me as I explored the hotel. I could see this as being really fun in the winter and with a group."
United States
Wendy
The price is Rp2.891.410
Rp3.180.552 total
includes taxes & fees
17 Dec - 18 Dec
Summit Lodge

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel
3.0 star property
Newbury
9.2 out of 10, Wonderful, (379)
"Great stay in a good location "
United States
Richard
The price is Rp2.830.652
Rp3.342.255 total
includes taxes & fees
16 Dec - 17 Dec
Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (927)
"Great place to stay while skiing at okemo"
United States
Ken
The price is Rp2.813.174
Rp3.207.018 total
includes taxes & fees
15 Dec - 16 Dec
Pointe at Castle Hill Resort

Norwich Inn

Norwich Inn
3.0 star property
Norwich
9.4 out of 10, Exceptional, (404)
"Excellent Inn "
United States
Sam
The price is Rp2.979.634
Rp3.247.801 total
includes taxes & fees
17 Dec - 18 Dec
Norwich Inn

Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction
2.0 star property
White River Junction
6.2 out of 10, (1005)
"The room was a very nice, felt safe. Enjoyed the fun small talk with the women at the front desk. Also felt its a good location as well. "
United States
Ariel
The price is Rp1.202.674
Rp1.322.940 total
includes taxes & fees
20 Dec - 21 Dec
Super 8 by Wyndham White River Junction

Six South St Hotel

Six South St Hotel
2.5 star property
Hanover
9.4 out of 10, Exceptional, (859)
"Great location. Walking distance to Dartmouth. Very comfortable room and bed."
United States
ellen
The price is Rp2.813.174
Rp3.052.294 total
includes taxes & fees
18 Dec - 19 Dec
Six South St Hotel

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1001)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort

Best Western West Lebanon-Hanover Hotel

Best Western West Lebanon-Hanover Hotel
2.5 star property
West Lebanon
8.4 out of 10, Very good, (928)
"Friendly staff, clean rooms, easy check in/out"
United States
Tony
The price is Rp1.896.146
Rp2.057.319 total
includes taxes & fees
22 Dec - 23 Dec
Best Western West Lebanon-Hanover Hotel

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0 star property
Brownsville
9.0 out of 10, Wonderful, (778)
"Clean room, very nice staff, everything was excellent! "
United States
Karen
The price is Rp1.980.874
Rp2.431.315 total
includes taxes & fees
18 Dec - 19 Dec
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Windsor attractions

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.

Cornish Windsor Covered Bridge

Top Windsor Hotel Reviews

More cheap stays in Windsor

Find out more about Windsor

Top reasons to visit Windsor

  • Outdoor Adventure: Windsor is a haven for outdoor enthusiasts, offering thrilling activities like skiing and exploring scenic landscapes.
  • Historic Attractions: The town features charming historic bridges and state parks, perfect for cultural explorations.
  • Family-Friendly Atmosphere: Windsor provides a welcoming environment with activities suitable for families and travellers of all ages.
  • Charming Accommodations: A variety of lodgings, from pet-friendly hotels to agritourism experiences, cater to diverse preferences.
  • Picturesque Countryside: Immerse yourself in the stunning natural beauty of the Berkshire region and its captivating landscapes.

Find great hotels in and around Windsor

Discover a charming selection of accommodations in Windsor, Vermont, perfect for every type of traveller. Whether you're seeking pet-friendly lodgings, family-friendly hotels, or agritourism experiences, you'll find an array of options to suit your needs. Many establishments offer accessible accommodations and complimentary Wi-Fi, ensuring a comfortable stay. Enjoy the adventure that awaits in this picturesque town, where relaxation and exploration go hand in hand.

  • Sunset Motor Inn: Nestled 22.5km from Windsor, Sunset Motor Inn caters to business travellers seeking a convenient and comfortable stay. This hotel features well-appointed rooms that blend practicality with comfort, ideal for those who need to balance work and leisure. Guests can enjoy amenities such as complimentary Wi-Fi, a business centre, and free parking, ensuring a hassle-free experience. With its focus on providing a seamless stay for professionals, Sunset Motor Inn stands out for its inviting atmosphere and efficient service.
  • Windsor Mansion Inn: Located in the heart of Windsor, the Windsor Mansion Inn is a charming 3.5-star Bed & Breakfast that offers a unique nature-themed experience. Perfect for adventure seekers, this inn features a range of outdoor activities including skiing, mountain climbing, and zip-lining nearby. Guests can indulge in comfortable accommodations that reflect the beauty of the surrounding landscape. With its emphasis on adventure and recreation, the Windsor Mansion Inn is an ideal choice for those looking to combine business travel with thrilling outdoor experiences.
  • Super 8 by Wyndham White River Junction: Situated 19.3km from Windsor, Super 8 by Wyndham White River Junction is a pet-friendly motel that welcomes travellers with furry companions. This motel is ideal for those seeking a budget-friendly, comfortable stay without leaving their pets behind. Guests can take advantage of amenities such as free breakfast, complimentary Wi-Fi, and a welcoming atmosphere for pets. With its convenient location and relaxed vibe, Super 8 is perfect for families and business travellers alike who value convenience and comfort.

Where to stay in and around Windsor

Windsor, Vermont, offers a delightful mix of adventure and scenic beauty, perfect for outdoor enthusiasts. Surrounded by acres of picturesque countryside and ample green spaces, visitors can immerse themselves in the charming architectural styles and friendly atmosphere. Nearby areas boast family-friendly vibes and historical excursions, making it an ideal destination for all types of travellers. Experience the stunning landscapes and the welcoming spirit of the Berkshire region during your stay in this enchanting city.

  • Woodstock: Nestled approximately 19.3km from Windsor, Woodstock is a charming town celebrated for its picturesque landscapes and vibrant outdoor activities. The town attracts visitors year-round, with peak seasons in July and September to October, offering a delightful blend of adventure and relaxation. Outdoor enthusiasts flock to its renowned ski fields and resorts, while nature lovers can explore the nearby mountains and national parks. Woodstock's quaint shops and local eateries further enhance the travel experience, making it a perfect spot for those seeking both adventure and culture.
  • Cornish: just 1.6km from Windsor, Cornish offers a delightful escape into nature, particularly during the summer months from June to August when visitor numbers are at their highest. Known for its outdoor and adventure experiences, this small city features scenic ski fields and educational attractions. Visitors can enjoy the local mountains, iconic bridges, and historic monuments, all while soaking in the serene atmosphere. Cornish’s close-knit community vibe and stunning landscapes make it an ideal destination for those seeking a peaceful yet adventurous getaway.
  • Ascutney: Located within the Windsor area, Ascutney is a quaint village that captivates visitors with its breathtaking natural beauty and outdoor activities. Peak travel times occur from July to September, making it a popular choice for adventure seekers. Ascutney offers easy access to ski fields and resorts, along with stunning lakes and mountainous terrain perfect for hiking and exploration. With its proximity to national parks, this village serves as a fantastic base for outdoor enthusiasts eager to immerse themselves in the beauty of Vermont's landscapes.

Things to do in and around Windsor

Windsor, Vermont offers a delightful blend of outdoor adventure and winter sports, making it an ideal destination for ski enthusiasts. Visitors can enjoy various activities including skiing at local resorts and exploring scenic ski fields. With its picturesque landscapes, Windsor is perfect for those seeking an exhilarating ski vacation or simply wishing to immerse themselves in the great outdoors.

Shopping

For a delightful shopping experience in Windsor, visit The Sustainable Farmer and North Country Smokehouse for local goods. If you're up for a drive, explore Quechee Gorge Village, 17.7km away, for charming shops and unique souvenirs to take home.

Recreation

The Upper Valley Aquatic Center offers a family-friendly atmosphere with a variety of swimming activities, perfect for relaxation and fun. For golf enthusiasts, the Woodstock Country Club provides a scenic outdoor setting, while The Strong House Spa promises a rejuvenating experience focused on wellness and relaxation.

Adventure

Experience the thrill of flight at Morningside Flight Park, located 17.7km from Windsor, where you can glide through stunning landscapes. For outdoor enthusiasts, the Brownsville Trail offers a picturesque setting right in Windsor, while Arrowhead Recreation Area, 14.5km away, provides excellent skiing and sports activities.

Nightlife

The nightlife in Windsor offers diverse experiences. Enjoy the adventure vibes at Maple Lanes, an arcade adventure zone just 12.9km away. For a touch of romance and culture, the Woodstock Town Hall Theatre awaits 19.3km from Windsor. Thrill-seekers can also ride the Timber Ripper Mountain Coaster, located 27.4km away.

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

Booking tips and Expedia advantages for Windsor

For a budget-friendly visit to Windsor, Vermont, consider travelling during the off-peak months of April to May and November, when hotel prices are lower. Tuesdays are the best day for affordable stays, while Fridays tend to be pricier. Use Expedia’s search tool to compare hotel prices and filter for eco-friendly options. Additionally, consider package deals that combine flights, hotels, and activities for further savings. Explore free local attractions to maximise your experience without overspending.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Windsor are April to May and November, where the prices are slightly lower. This is in comparison to February, October and December, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Windsor is Tuesday. The most expensive day to stay in Windsor is Friday.
  • Find cheap hotels on Expedia: Expedia's search tool enables you to specify your budget, desired location, and additional preferences. You can organise your results to display prices from lowest to highest, ensuring that the most affordable hotels appear at the top of your list. Furthermore, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will show you sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can potentially save money by combining your Windsor hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Windsor

Windsor, Vermont, is an ideal destination for outdoor enthusiasts and adventure seekers, particularly those interested in skiing. Visitors can explore a variety of attractions, such as historic bridges, national state parks, and environmental centres, which provide enriching experiences for families and culture lovers alike. Whether you're keen on outdoor activities or cultural exploration, Windsor offers a delightful array of options to enjoy during your stay.

  • Blow-Me-Down Bridge: Situated just 805m from Windsor, this historic bridge offers a glimpse into the region's cultural heritage. Its charming architecture and scenic surroundings make it a perfect spot for photography and leisurely strolls.
  • Mount Ascutney: Located 6.4km away, Mount Ascutney is a haven for adventure enthusiasts. Explore hiking trails that provide breathtaking views and immerse yourself in the natural beauty of the outdoors, ideal for both casual walkers and seasoned climbers.
  • Saint-Gaudens National Historic Site: Only 3.2km from Windsor, this historic site celebrates the life and work of sculptor Augustus Saint-Gaudens. Visitors can appreciate stunning sculptures and the serene landscape, enriching their understanding of American art and history.

Best time to go to Windsor

The best time to visit Windsor is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January16.7°F (-8.5°C)Light RainMostly CloudyAverageAverage
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 LowSlightly High

The nearest major airports for your trip to Windsor

Windsor, Vermont, can be easily accessed via three major airports. Lebanon Municipal Airport (LEB) is located 17.7km away and offers nearby accommodation options such as the Windsor Mansion Inn, a charming 3.5-star bed and breakfast, and the Residence Inn by Marriott Hanover Lebanon, just 6.4km distant. Rutland Southern Vermont Regional Airport (RUT), situated 45.1km away, features hotels like the Cortina Inn and Killington Mountain Lodge, with convenient transportation services available. Finally, Hartness State Airport (VSF) is 19.3km from Windsor, with options like the Inn at Weathersfield, a 4-star establishment, ensuring a comfortable stay for visitors.

Frequently asked questions

What's the best place to stay in Windsor?
Based on Expedia's traveller preferences, Fat Sheep Farm & Cabins is a top place to stay in Windsor. Two other options for your stay in the area are Woodstock Inn & Resort and Killington Mountain Lodge, Tapestry Collection by Hilton. See all available top hotels, or vacation rentals in Windsor.
If I need to cancel my hotel reservation in Windsor, will I receive a refund?
Yes, the majority of hotel room reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a reservation that's non-refundable, you may still be able to cancel and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.
What's the best dog-friendly hotel in Windsor?
Fat Sheep Farm & Cabins is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Windsor.
What are some accommodation options with pools in Windsor?
Woodstock Inn & Resort: Offers a seasonal outdoor pool, an indoor pool and 4 restaurants. The Mountain Inn at Killington and Align Inn Vermont are a couple of other choices that feature an on-site pool. View all hotels with pools in Windsor.
What's it like to stay in Windsor?
Visitors can enjoy all that Windsor has to offer, including the breweries, golf courses and forests. The scenic and rural setting also entices those visiting the city. In Windsor, there are 23 hotels and other accommodation options to choose from. Find out more about Windsor.
What should I do while I'm visiting Windsor?
The picturesque setting of Connecticut River and Paradise Park exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are American Precision Museum and Harpoon Brewery. Take a look at what more there is to see and do in Expedia's Windsor guide.
What's the best way to get around Windsor?
To venture out into the surrounding area, take a train from Windsor Station. If you want to venture out around the area, you may want a rental car in Windsor for your journey.
What's the weather like in Windsor?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -6°C. The snowiest months in Windsor are March, January, November and February, with each month seeing an average of 38 cm of snowfall.