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Windsor hotels from HK$618

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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

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (257)
Victorian charm awaits at this quiet Woodstock B&B where travellers rave about the delicious morning meal. Relax in the garden, enjoy evening drinks at the bar, or explore nearby Union Arena and Five Elm Arches from this peaceful retreat.

"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (329)
Located in South Woodstock, this inn features the Ransom Tavern for dinner and a cosy bar/lounge with terrace. Free WiFi and parking add convenience while Union Arena and VINS Nature Centre provide nearby exploration options.

"Nice place to stay. Would stay there again & recommend it to friends and family "
United States
Deborah
Kedron Valley Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1001)
Discover a tranquil retreat near the train station in Woodstock featuring an indoor pool, hot tub, and on-site 506 Bistro and Lounge. Guests love the helpful staff, complimentary breakfast, and convenient access to Union Arena Community Centre.

"Rearaurant staff was top notch. "
United States
Daniel
The price is HK$2,529
HK$3,067 total
includes taxes & fees
29 Dec - 30 Dec
On The River Inn

Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
8.8 out of 10, Excellent, (3)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
The price is HK$1,432
HK$2,330 total
includes taxes & fees
24 Dec - 25 Dec
Brook Road Condo

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
This cosy Woodstock B&B offers free continental breakfast daily, plus convenient WiFi and parking. Explore nearby attractions like Billings Park and Trail or Red Wagon Toy Company, then return to this welcoming retreat.

"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is HK$1,937
HK$2,131 total
includes taxes & fees
6 Jan - 7 Jan 2026
Stay At Jimmy's

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.4 out of 10, Exceptional, (183)
Surrounded by mountain splendour, this family-friendly retreat offers Kent Bistro dining and relaxing amenities including a sauna. Just minutes from Killington Resort and Pico Mountain skiing, guests consistently praise the attentive staff.

"Staff was amazing! They made the stay even better with their hospitality and overall service. I recommend this Lodge to anyone looking to go to Killington who wants a fun and relaxing stay. "
United States
Jaden
The price is HK$1,703
HK$2,068 total
includes taxes & fees
4 Jan - 5 Jan 2026
Mountain Meadows Lodge

Royal Inn Claremont

Royal Inn Claremont
2.0 star property
Claremont
6.6 out of 10, (318)
Located in Claremont, this welcoming motel offers convenient amenities including complimentary WiFi and self parking. Nearby hiking trails and kayaking spots provide outdoor adventure, while Tremont Square and Claremont Opera House are just minutes away.

"Affordable"
United States
Cheryl
The price is HK$787
HK$854 total
includes taxes & fees
24 Dec - 25 Dec
Royal Inn Claremont

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
This charming B&B offers free WiFi and parking with a daily buffet breakfast. Outdoor enthusiasts will love the nearby hiking trails and mountain biking, while popular attractions like Bonnie's Bundles Dolls are just minutes away.

"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is HK$1,625
HK$1,771 total
includes taxes & fees
30 Dec - 31 Dec
Stone Hearth Inn and Eatery

Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
2.0 star property
Ludlow
9.6 out of 10, Exceptional, (211)
Discover Vermont's beauty at this Ludlow motel offering free WiFi, parking, and an area shuttle to nearby Okemo Mountain Resort. After outdoor fun, unwind at the on-site bar before retiring to comfortable accommodation. Dorsey Park is also located close by.

"The bar was wonderful! Clean and great guest services"
United States
Mariah
The price is HK$2,395
HK$2,634 total
includes taxes & fees
6 Jan - 7 Jan 2026
Main and Mountain Bar & Motel

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (70)
This inviting Perkinsville inn offers free Wi-Fi, breakfast and parking. Unwind with drinks at the bar/lounge or savour a meal at the restaurant. North Springfield Lake and Stoughton Pond Recreation Areas await nearby.

"The location of the Inn was in an area that was just wonderful. Staff was very friendly and the menu options were very tasty. Room was clean and well maintained. "
United States
Joshua
The Inn at Weathersfield

The Hartness House

The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very good, (329)
Beautifully situated with easy access to transport, this charming hotel offers free WiFi and parking. Outdoor enthusiasts will appreciate nearby hiking trails, kayaking, and mountain biking opportunities, with Muckross State Park just a short drive away.

"nice folks, practical place to stay. "
United States
Mark
The price is HK$1,270
HK$1,398 total
includes taxes & fees
25 Dec - 26 Dec
The Hartness House

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (806)
Tucked away in Springfield, this tranquil hotel offers a refreshing indoor swimming experience and fitness centre. Guests can explore nearby Baltimore Covered Bridge while enjoying free breakfast, WiFi, and parking throughout their stay.

"so clean and friendly it was a perfect stay!"
United States
Colette
The price is HK$1,183
HK$1,302 total
includes taxes & fees
5 Jan - 6 Jan 2026
Best Western Springfield Hotel

The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm
3.0 star property
Quechee
9.0 out of 10, Wonderful, (1000)
Set along Wilderness Trails in scenic Quechee, this historic inn offers complimentary gourmet breakfast and convenient access to Vermont Institute of Natural Science. Enjoy dining at the acclaimed restaurant, unwind in the garden, or sip drinks at the welcoming bar.

"Beautiful historic property. We had dinner at the hotel restaurant and it was fantastic!"
United States
Dion
The price is HK$1,183
HK$1,302 total
includes taxes & fees
8 Jan - 9 Jan 2026
The Quechee Inn at Marshland Farm

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.8 out of 10, Good, (9)
Tucked in charming Goshen, this welcoming cottage offers a private garden and fully equipped kitchen for your rural escape. Explore nearby Olive G. Pettis Library and Gunnison Lake, then return to relax with Smart TV entertainment.

"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
Brook Road Cabin

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (51)
Surrounded by seasonal adventure, this charming 3-star B&B offers complimentary continental breakfast, WiFi, and parking. Winter enthusiasts will love the cross-country skiing and snowboarding options, with Billings Park and Dana House Museum just minutes away.

"Charming bed and breakfast"
United States
Nicholas
The price is HK$1,300
HK$1,431 total
includes taxes & fees
30 Dec - 31 Dec
The Vesper

The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (370)
Set along the Connecticut River, this welcoming retreat offers complimentary breakfast and parking. Unwind at the bar after exploring nearby attractions, or relax in the hot tub. Clean rooms include refrigerators and microwaves for added convenience.

"Great place to stay! "
United States
Candace M
The price is HK$1,118
HK$1,213 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Common Man Inn & Restaurant

Killington Grand Hotel

Killington Grand Hotel
3.5 star property
Base Area
8.8 out of 10, Excellent, (193)
This ski-in/ski-out hotel sits at the base of Killington Resort, offering direct mountain access. Unwind in 2 hot tubs or the outdoor pool after hitting the slopes. The full-service spa provides rejuvenating deep-tissue massages, while the restaurant and bar complete your alpine retreat.

"Fantastic....Perfect place for a fall getaway."
United States
Justin
Killington Grand Hotel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (549)
Enjoy a peaceful retreat near Killington and Sugarbush ski resorts. This well-maintained motel offers clean rooms and friendly staff in a beautiful Vermont setting. Free WiFi and parking make it easy to explore Ottaquechee River and local hiking trails.

"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 HK$644
HK$1,195 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sleep Woodstock Motel

Newport Motel

Newport Motel
2.0 star property
Newport
8.8 out of 10, Excellent, (267)
Just 36 minutes from Lebanon Municipal Airport, this clean motel offers complimentary WiFi and parking. Close to Wendell Marsh Wildlife Management Area and Newport Historical Society for local exploration.

"Nice place to short stay "
Mexico
Vanessa
The price is HK$819
HK$889 total
includes taxes & fees
21 Jan - 22 Jan 2026
Newport Motel
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, Vermont, is perfect for outdoor enthusiasts, offering skiing and a range of adventure activities amidst stunning landscapes.
  • Historic Bridges and Parks: Explore historic bridges and national state parks, blending outdoor fun with cultural experiences.
  • Scenic Countryside: Enjoy the picturesque countryside with its ample green spaces and charming architecture.
  • Family-Friendly Atmosphere: Nearby towns provide a welcoming vibe, rich history, and family-friendly options for excursions.
  • Variety of Accommodations: Discover diverse lodging options, from pet-friendly hotels to agritourism properties, ensuring a comfortable stay.

Find great hotels near Windsor

Discover a range of delightful accommodation options in Windsor, Vermont, catering to every traveller's needs. Whether you seek adventure, a pet-friendly environment, or family-friendly experiences, Windsor offers a variety of hotels and agritourism properties. Enjoy accessible accommodations, including those with free Wi-Fi, ensuring a comfortable stay for everyone. Explore the charm of this picturesque town while relishing the hospitality of its welcoming lodgings.

  • Super 8 by Wyndham White River Junction: A welcoming retreat for those on a budget, Super 8 by Wyndham White River Junction combines practicality with comfort. Located 19.3km from Windsor, this motel is ideal for pet owners and business travellers alike. The property features a pet-friendly policy, allowing certain pets at no extra charge, making it a convenient choice for those who travel with furry companions. Guests appreciate its complimentary breakfast and free Wi-Fi, ensuring a hassle-free stay. The motel’s straightforward amenities create a relaxed environment, perfect for unwinding after a day of exploring.
  • White River Inn and Suites: Embracing inclusivity, White River Inn and Suites stands out for its LGBTQIA-friendly ethos. Situated 19.3km from Windsor, this hotel welcomes all with open arms, making it an excellent option for diverse travellers. The property provides a comfortable atmosphere, allowing pets with some restrictions, and offers a variety of amenities tailored for business visitors. Guests can enjoy the well-appointed rooms and the convenience of a variable pet fee, ensuring a pleasant stay for both you and your four-legged friend. Its dedication to a welcoming environment is complemented by its proximity to local attractions.
  • Best Western West Lebanon-Hanover Hotel: A family-friendly haven, Best Western West Lebanon-Hanover Hotel is located just 17.7km from Windsor. This hotel caters to both families and business travellers, featuring a range of amenities for children, including complimentary cribs. Its affiliation with LGBTQIA travel guides highlights its inclusive nature, ensuring all guests feel at home. With spacious rooms and convenient access to local dining and attractions, this hotel provides a comfortable base for exploring the area. Guests appreciate the welcoming atmosphere and attentive service, making it a preferred choice for families and business trips alike.

Where to stay near Windsor

Windsor, Vermont, offers a delightful blend of outdoor adventures and scenic beauty, making it ideal for both ski enthusiasts and nature lovers. Explore the surrounding countryside, with its ample green spaces and charming architectural styles. Nearby towns provide a family-friendly atmosphere, rich history, and friendly locals, perfect for excursions. Don't miss the stunning views of the beautiful Berkshire mountains while enjoying the vibrant community vibe that Windsor and its neighbouring areas have to offer.

  • Woodstock: Nestled 19.3km from Windsor, Woodstock is a picturesque town renowned for its charming New England architecture and vibrant community atmosphere. Visitors flock here year-round, particularly in July and during the autumn months, to indulge in outdoor adventures, including skiing and exploring the nearby national and state parks. The scenic landscapes, featuring serene lakes and majestic mountains, make it a haven for nature enthusiasts. Highlights include the popular ski resorts that draw both beginners and seasoned skiers alike, ensuring an exhilarating experience amidst stunning vistas.
  • Quechee: Also located 19.3km from Windsor, Quechee is famed for its breathtaking natural beauty and outdoor recreation. This quaint town attracts visitors predominantly in June to July and September, offering a range of adventure activities, particularly skiing in the colder months. The Quechee Gorge, often referred to as Vermont's Grand Canyon, provides a spectacular backdrop for hiking and photography. With its tranquil lakes and charming covered bridges, Quechee is perfect for those seeking both adventure and relaxation in a serene setting.
  • White River Junction: Situated 19.3km from Windsor, White River Junction is a vibrant community that offers a unique blend of history and modern amenities. Visitors are drawn here for its thrilling outdoor experiences, particularly skiing, with peak arrivals in the summer and autumn months. The town is home to historic colleges and universities, adding a cultural depth to the area. With its proximity to scenic lakes and the impressive canyon gorge, White River Junction is a must-visit for those looking to explore the great outdoors while enjoying a rich local heritage.

Things to do in and around Windsor

Windsor, Vermont, is an ideal destination for outdoor enthusiasts, offering a range of adventure activities, particularly in skiing. Visitors can enjoy top-notch ski resorts and fields, making it a perfect getaway for winter sports lovers. Whether you are keen on hitting the slopes or exploring the scenic beauty of the area, Windsor provides an exhilarating experience for all adventurers.

Shopping

The Sustainable Farmer offers local goods and unique gifts right in Windsor. North Country Smokehouse, 11.3km away, is perfect for gourmet treats. If you're up for a drive, visit Quechee Gorge Village, 17.7km away, where charming shops await with handcrafted souvenirs.

Recreation

Woodstock Country Club offers a picturesque golf course set amidst beautiful landscapes, perfect for sports enthusiasts. The Upper Valley Aquatic Center is ideal for families, providing a variety of water activities. For ultimate relaxation, visit The Strong House Spa, where wellness treatments rejuvenate the body and mind.

Adventure

The Green Mountain Rock Climbing Center, located 17.7km from Windsor, offers exhilarating climbing experiences amidst stunning landscapes. For a scenic hike, the Brownsville Trail in Windsor provides a refreshing outdoor adventure. Meanwhile, the Arrowhead Recreation Area, 14.5km away, invites you to enjoy thrilling skiing in a vibrant atmosphere.

Nightlife

In Windsor, the Woodstock Town Hall Theatre offers an enchanting evening of culture and romance, located 19.3km away. For a lively adventure, Maple Lanes, 12.9km distant, provides arcade excitement, while the Timber Ripper Mountain Coaster, 27.4km away, promises exhilarating amusement rides.

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

Booking tips and Expedia advantages for Windsor

To save money on your trip to Windsor, consider visiting during the cheaper months of April to May or November, and aim to book your stay on a Tuesday for the best rates. Use Expedia’s search tool to filter for budget-friendly accommodations, including eco-certified hotels. Save further by bundling your hotel, flights, and activities in a package deal. Additionally, explore free local attractions to enhance your experience without straining your wallet. By planning wisely, you can enjoy Windsor 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 choose your budget, preferred location, and additional criteria. You can organise your search results by price, displaying the most affordable hotels at the top. Furthermore, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your hotel reservation in Windsor with your flights and activities when you book an Expedia package.

Find the best attractions near Windsor

Windsor, Vermont, is an excellent destination for outdoor enthusiasts and adventure seekers. The area boasts a variety of attractions, including historic bridges, national state parks, and environmental centres. These points of interest provide a perfect blend of outdoor activities, cultural experiences, and family-friendly options, ensuring that visitors can fully enjoy the natural beauty and rich heritage of this charming town.

  • Quechee Gorge Bridge: Experience breathtaking views from this stunning canyon bridge, perfect for outdoor enthusiasts. The gorge offers scenic trails and adventure activities, making it a fantastic spot for hiking and photography.
  • Simon Pearce Mill: This charming landmark is renowned for its craftsmanship and family-friendly atmosphere. Visitors can enjoy delicious dining while watching artisans create beautiful glassware, making it an ideal place for a leisurely family outing.
  • VINS Nature Center: Engage with nature at this eco-friendly centre, which focuses on environmental education. Discover local wildlife and participate in interactive exhibits, promoting business sustainability and conservation awareness.

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

For your visit to Windsor, Vermont, you can fly into several nearby airports. Lebanon Municipal Airport (LEB) is located 17.7km away, with nearby hotels such as the 4-star Hanover Inn Dartmouth, 8.0km from the airport, and the 3-star Hotel Coolidge, just 3.2km away. Rutland Southern Vermont Regional Airport (RUT) is 45.1km from Windsor, with options like the 3.5-star Killington Mountain Lodge, 17.7km away. Additionally, Hartness State Airport (VSF) in Springfield is 13.2km from Windsor, offering stays at the 4-star Inn at Weathersfield, just 1.6km away. Each of these airports provides convenient access to local accommodations.

Frequently asked questions

What's the best place to stay in Windsor?
Killington Mountain Lodge, Tapestry Collection by Hilton, located 22.8 mi (36.8 km) from the heart of Windsor, is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Woodstock Inn & Resort and The Mountain Inn at Killington. See all available top hotels, or vacation rentals in Windsor.
What are some of the best holiday rentals that Windsor has to offer?
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This holiday home rental outside of Windsor is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub. See all 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: Provides a seasonal outdoor pool, an indoor pool and 4 restaurants. The Mountain Inn at Killington and White River Inn and Suites 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.

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