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

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22 Sep - 23 Sep
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23 Sep - 24 Sep
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25 Sep - 27 Sep
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2 Oct - 4 Oct

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Our top choices for Windsor hotels

1. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
Windsor
United States
Jessica
AED 773
AED 1,042 total
includes taxes & fees
22 Oct - 23 Oct
Fat Sheep Farm & Cabins

2. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Shannon
AED 657
AED 777 total
includes taxes & fees
28 Sep - 29 Sep
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3. Claremont Motor Lodge

Claremont Motor Lodge
Claremont
United States
EDWARD S
AED 419
AED 454 total
includes taxes & fees
18 Oct - 19 Oct
Claremont Motor Lodge

4. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Victoria
AED 674
AED 732 total
includes taxes & fees
18 Oct - 19 Oct
The Common Man Inn & Restaurant

5. Align Inn Vermont

Align Inn Vermont
Quechee
United States
Joanne
AED 778
AED 855 total
includes taxes & fees
18 Oct - 19 Oct
Align Inn Vermont

6. Royal Inn Claremont

Royal Inn Claremont
Claremont
United States
Eva
AED 441
AED 478 total
includes taxes & fees
28 Sep - 29 Sep
Royal Inn Claremont

7. 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
AED 724
AED 796 total
includes taxes & fees
18 Oct - 19 Oct
Holiday Inn Express Hotel & Suites White River Junction by IHG

8. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
AED 891
AED 1,106 total
includes taxes & fees
24 Sep - 25 Sep
The Inn at Weathersfield

9. Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon
West Lebanon
United States
amber
AED 615
AED 667 total
includes taxes & fees
19 Oct - 20 Oct
Fireside Inn & Suites West Lebanon

10. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
AED 658
AED 724 total
includes taxes & fees
18 Oct - 19 Oct
Best Western Springfield Hotel

11. Newport Motel

Newport Motel
Newport
United States
Andrew
AED 393
AED 426 total
includes taxes & fees
24 Sep - 25 Sep
Newport Motel

12. White River Inn and Suites

White River Inn and Suites
White River Junction
United States
kevin
AED 492
AED 542 total
includes taxes & fees
21 Oct - 22 Oct
White River Inn and Suites

13. Sleep Woodstock Motel

Sleep Woodstock Motel
Woodstock
United States
michelle
AED 340
AED 516 total
includes taxes & fees
28 Sep - 29 Sep
Sleep Woodstock Motel

14. Hotel Coolidge

Hotel Coolidge
White River Junction
United States
Elizabeth
AED 657
AED 723 total
includes taxes & fees
19 Oct - 20 Oct
Hotel Coolidge

15. Kedron Valley Inn

Kedron Valley Inn
South Woodstock
United States
Kathryn
AED 1,484
AED 1,633 total
includes taxes & fees
24 Sep - 25 Sep
Kedron Valley Inn

16. Comfort Inn White River Junction

Comfort Inn White River Junction
White River Junction
United States
Crystal
AED 517
AED 569 total
includes taxes & fees
21 Oct - 22 Oct
Comfort Inn White River Junction

17. Hampton Inn White River Junction

Hampton Inn White River Junction
White River Junction
United States
Philip
AED 778
AED 855 total
includes taxes & fees
18 Oct - 19 Oct
Hampton Inn White River Junction

18. Quality Inn Lebanon - Hanover

Quality Inn Lebanon - Hanover
Lebanon
United States
Karol
AED 543
AED 589 total
includes taxes & fees
22 Oct - 23 Oct
Quality Inn Lebanon - Hanover

19. The Jackson

The Jackson
West Woodstock
United States
Laura
AED 1,319
AED 1,451 total
includes taxes & fees
24 Sep - 25 Sep
The Jackson

20. On The River Inn

On The River Inn
West Woodstock
United Kingdom
Laura
AED 1,392
AED 1,612 total
includes taxes & fees
24 Sep - 25 Sep
On The River Inn
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Stay near popular Windsor attractions

A snow-covered landscape with a wooden covered bridge over a river, surrounded by trees and a snowy path.

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.
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A calm river with dense greenery and trees reflecting on the water.

Paradise Park

8.8/10 (8 reviews)
Paradise Park offers diverse ecosystems around Lake Runnemede, with well-maintained trails through forests and meadows. Observe abundant wildlife including birds, turtles, and beavers in this peaceful natural sanctuary.
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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.
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American Precision Museum

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

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

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Wonderful inn! Everything was wonderful: rooms, food, etc!!"
Ann 2-night trip
Posted 3 hours ago
Woodstock Inn & Resort
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very nice stay and nice rooms."
Nicole 1-night trip
Posted 7 hours ago
Pointe at Castle Hill Resort
The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Beautiful property with unique blend of modern and rustic design"
Nicholas 1-night trip
Posted 12 hours ago
The Mountain Inn at Killington
Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"This is a beautiful clean well accommodated property on the edge of a magnificent pond. Ive nothing but positive memories and will definitely return."
E William 1-night trip
Posted 1 day ago
Mountain Meadows Lodge
Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"The room was very clean and comfortable. Breakfast and coffee were great and the location was perfect."
Caren 2-night trip
Posted 1 day ago
Align Inn Vermont
Mountain Sports Inn

Mountain Sports Inn

8/10 Good
"Jenny @ the front desk was very helpful and kind. The hotel itself is dated. Older beds. Stark shelving in bathrooms though functional. Breakfast was hot and fresh, cook was not.. 😆. Overall we enjoyed our stay and would stay again. Probably request a room away from the main door and towards the back of the property. Cars coming in and out and hallway door noise was above average."
Adam 2-night trip
Posted 1 day ago
Mountain Sports Inn
Hotel Coolidge

Hotel Coolidge

8/10 Good
"We loved the coffee in the lobby and dinner recommendations. Comfortable room."
Sharon 1-night trip
Posted 1 day ago
Hotel Coolidge
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"N/A"
Robert 1-night trip
Posted 1 day ago
Killington Mountain Lodge, Tapestry Collection by Hilton
The Jackson

The Jackson

8/10 Good
"The Hostess at the wine and cheese hour was very kind and helpful. That was the only time we saw anyone! The house is divided into separate areas and we were in the oldest part. The bed was comfortable, bathroom nice, amenities nice but wouldn’t book again because of the very narrow and steep stairs. My husband is 80, hauling luggage up those kind of stairs is dangerous. That would be the only reason not to return."
Robin 1-night trip
Posted 1 day ago
The Jackson

More cheap stays in Windsor

Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction

442 North Hartland Rd White River Junction VT
AED 353
AED 388 total
21 Oct - 22 Oct
includes taxes & fees
6.2/10 (1,005 reviews)
Super 8 by Wyndham White River Junction
The Mountain Inn at Killington

The Mountain Inn at Killington

47 Old Mill Rd Killington VT
AED 493
AED 569 total
18 Oct - 19 Oct
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
The Mountain Inn at Killington
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

25 Airport Road West Lebanon NH
AED 615
AED 667 total
19 Oct - 20 Oct
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Fireside Inn & Suites West Lebanon
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
AED 724
AED 796 total
18 Oct - 19 Oct
includes taxes & fees
Holiday Inn Express Hotel & Suites White River Junction by IHG
Align Inn Vermont

Align Inn Vermont

5817 Woodstock Rd Quechee VT
AED 778
AED 855 total
18 Oct - 19 Oct
includes taxes & fees
9.4/10 Exceptional! (1,347 reviews)
Align Inn Vermont
Six South St Hotel

Six South St Hotel

6 South Street Hanover NH
AED 1,187
AED 1,288 total
29 Sep - 30 Sep
includes taxes & fees
9.4/10 Exceptional! (990 reviews)
Six South St Hotel

Find out more about Windsor

Top reasons to visit Windsor

  • Outdoor Adventures: Windsor is perfect for skiing and outdoor activities, offering scenic landscapes and adventure-filled experiences.
  • Historic Charm: Explore the town's rich history through its charming downtown shops and historic bridges.
  • Vibrant Local Scene: Enjoy live music performances that contribute to Windsor's lively atmosphere.
  • Diverse Accommodations: Choose from a variety of lodging options, including pet-friendly and family-oriented stays.
  • Natural Beauty: Immerse yourself in stunning natural settings and national state parks surrounding the area.

Find great hotels near Windsor

Discover the charm of Windsor, Vermont, where a variety of accommodations await to enhance your vacation experience. Whether you're seeking adventure, a pet-friendly environment, or a family-oriented stay, Windsor's hotels cater to every traveler’s needs. With many options to choose from, including agritourism properties and traditional hotels, you'll find the perfect spot to relax and explore the beautiful surroundings. Don't miss out on reading hotel reviews and checking room rates to ensure a memorable visit.

  • Super 8 by Wyndham White River Junction: Conveniently located 19.3km from Windsor, the Super 8 by Wyndham White River Junction is an ideal choice for travelers seeking a comfortable and budget-friendly motel experience. This pet-friendly property welcomes furry companions with a flexible pet policy. Whether you're on a business trip or a leisurely getaway, you can enjoy amenities such as complimentary breakfast, free Wi-Fi, and a friendly atmosphere tailored for both solo travelers and families alike.
  • Fireside Inn & Suites West Lebanon: Situated just 17.7km from Windsor, Fireside Inn & Suites West Lebanon offers a warm and inviting hotel experience perfect for business travelers and pet owners. With a focus on comfort, the hotel features cozy accommodations with modern amenities. Guests can take advantage of the pet-friendly policy, which includes food and water bowls for your furry friends. Additionally, the hotel's proximity to local attractions and business hubs makes it a great choice for both leisure and work-related stays.
  • White River Inn and Suites: Located 19.3km from Windsor, the White River Inn and Suites is perfect for adventurous travelers seeking a blend of business and leisure. This hotel not only welcomes pets but also offers a plethora of onsite and nearby adventure sports activities, including skiing, snowboarding, and bicycle rentals. With a focus on outdoor experiences, guests can enjoy comfortable accommodations while exploring the natural beauty of the area. The friendly staff and extensive amenities make it an excellent choice for your Vermont getaway.

Where to stay in and around Windsor

Windsor, Vermont, offers an ideal getaway for adventure seekers and families alike. Explore its charming downtown shops, enjoy scenic outdoor activities, and immerse yourself in the friendly, historical atmosphere. With ski vacations nearby and a perfect blend of urban vibes and natural beauty, Windsor is a delightful base for excursions to nearby towns, making it a true Vermont escape.

  • Woodstock: Located 19.3km from Windsor, Woodstock is a charming city that offers a mix of outdoor adventure and picturesque scenery. Known for its vibrant arts scene and historic architecture, visitors flock here for skiing during the winter months and hiking in the summer. With peaks in visitor numbers from July to October, Woodstock features popular ski resorts and beautiful lakes, making it an ideal destination for both winter sports enthusiasts and summer adventurers. Don't miss exploring the nearby national state park for breathtaking views and nature trails.
  • Cornish: Just 1.6km away from Windsor, the quaint city of Cornish is a seasonal gem that draws visitors particularly from June to August. Renowned for its stunning scenery and outdoor activities, Cornish is perfect for those looking to immerse themselves in nature. Enjoy the thrill of skiing or take in the sights of the local mountains, iconic bridges, and historical monuments. This tight-knit community also offers educational experiences that highlight its rich cultural heritage, making it a lovely stop for travelers seeking both adventure and learning.
  • Ascutney: Nestled within the Windsor area, Ascutney is a delightful village known for its year-round appeal, peaking in visitor numbers from July to September. It offers an exciting blend of skiing, sports, and adventure activities. The nearby ski fields and resorts cater to both beginners and seasoned skiers alike. Additionally, Ascutney is in close proximity to beautiful lakes and majestic mountains, as well as national state parks, providing numerous opportunities for outdoor exploration and relaxation amidst nature's beauty.

Things to do in and around Windsor

Windsor, Vermont, offers a perfect getaway for adventure enthusiasts and outdoor lovers, featuring activities like skiing at its renowned ski resorts and fields. Visitors can also enjoy the lively local scene, including live music performances that add to the vibrant atmosphere. Whether you're hitting the slopes or soaking in the local culture, Windsor promises a memorable experience for all vacationers.

Shopping

In Windsor, you can visit The Sustainable Farmer for unique gifts. North Country Smokehouse is also nearby for delicious local food products, just 11.3km away. If you're up for a drive, check out Quechee Gorge Village, located 17.7km from Windsor, for more shopping options.

Recreation

The Upper Valley Aquatic Center offers a family-friendly atmosphere with swimming and fitness activities, perfect for all ages. For golf enthusiasts, the Woodstock Country Club provides an outdoor sports experience amidst beautiful scenery. The Strong House Spa is a tranquil haven for rejuvenating body treatments and relaxation.

Adventure

Experience the Brownsville Trail, a captivating outdoor adventure right in Windsor, perfect for hiking and nature walks. For thrilling winter sports, head to Arrowhead Recreation Area, located 14.5km away, offering great skiing opportunities. Enjoy breathtaking views at Morningside Flight Park, 17.7km from Windsor, with exhilarating scenic flights.

Nightlife

In Windsor, head to Maple Lanes for a fun-filled arcadeAdventureZone just 12.9km away, perfect for family vibes. For a more cultural experience, the Woodstock Town Hall Theatre and Lebanon Opera House, both within 12 and 20.9km respectively, offer romance and engaging entertainment.

*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 and November, with Tuesdays being the most affordable days to stay. Use Expedia’s search tool to compare hotel rates and find package deals that combine accommodations with flights and activities for additional savings. Take advantage of free local attractions and opt for public transportation or walking to explore the area, as this can significantly reduce travel costs while allowing you to enjoy Windsor's charm.

  • 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: Utilize Expedia’s search tool to refine your options based on your budget, desired location, and preferred hotel type. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Windsor with flights and activities by booking a package through Expedia.

Find the best attractions near Windsor

Windsor, Vermont, offers a fantastic mix of adventure and outdoor activities, making it perfect for ski vacations. Visitors can explore historic bridges, national state parks, and environmental centers, catering to those seeking culture, family experiences, and outdoor fun. Don't miss the chance to immerse yourself in the natural beauty and rich history that Windsor has to offer.

  • Blow-Me-Down Bridge: This historic bridge, located 805m from Windsor, offers a glimpse into the area's rich cultural heritage. Its unique design and picturesque setting make it an ideal spot for photography and leisurely walks.
  • Mount Ascutney: A mere 6.4km from Windsor, Mount Ascutney presents incredible outdoor adventures. Hike or bike the scenic trails to enjoy breathtaking views, perfect for nature lovers and thrill-seekers alike.
  • Saint-Gaudens National Historic Site: Just 3.2km away, this historic site celebrates the works of renowned sculptor Augustus Saint-Gaudens. Explore beautiful gardens and impressive sculptures, immersing yourself in the area's artistic culture.

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

When visiting Windsor, Vermont, you have a few airport options for your arrival. Lebanon Municipal Airport (LEB) is situated 17.7km away, with nearby hotel choices like 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, offering accommodations like the 3.5-star Killington Mountain Lodge, 17.7km away. Hartness State Airport (VSF) is located 13.2km from Windsor, with nearby options such as the 4-star Inn at Weathersfield, just 1.6km away. Each airport provides convenient access to these comfortable lodging choices.

Frequently asked questions

What's the best place to stay in Windsor?
Based on our traveler data, Fat Sheep Farm & Cabins is one of the top choices for your stay. This cabin offers free parking and private decks. Other good options for your visit to the area are Align Inn Vermont and The Mountain Inn at Killington. See all available top hotels, or vacation rentals in Windsor.
What are some of the best vacation rentals in Windsor?
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home near Windsor is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. See all vacation rentals in Windsor.
If I need to cancel my hotel reservation in Windsor, will I receive a refund?
Yes, you'll find most hotel reservations are fully refundable as long as you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.
Where can I learn more about changing or cancelling my trip to Windsor?
To find more details about changing or cancelling your trip to Windsor, go to https://www.expedia.com/service/.
What's the best pet-friendly accommodation in Windsor?
Fat Sheep Farm & Cabins is a top pet-friendly option for your stay. See more pet-friendly hotel accommodations in Windsor.
Where is the best hotel to stay close to Mt Ascutney State Park?
Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel is one of the top choices for your stay based on our traveler data, and this 3-star resort offers a restaurant and an indoor pool. It's located 2.2 mi (3.5 km) from Mt Ascutney State Park. Other good choices within 5 miles include Windsor Mansion Inn and Snapdragon Inn.
What about the best place to stay close to Mount Ascutney?
One of the top choices for your stay is Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel, located 1.8 mi (2.8 km) from Mount Ascutney, and this 3-star resort offers a restaurant and an indoor pool. Windsor Mansion Inn and Rockledge Farm country living are other good choices within a few miles.
What are some accommodations with pools in Windsor?
Align Inn Vermont: Provides daily, an indoor pool, and free self parking. The Mountain Inn at Killington and Fireside Inn & Suites West Lebanon are a couple of other choices that feature an onsite pool. View all hotels with pools in Windsor.
What is the best hotel near Hartness State Airport (VSF)?
The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.
How is it staying 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 21 hotels and other accommodations to choose from. Find out more about Windsor.
What should I see while I'm in 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 agenda are American Precision Museum and Harpoon Brewery. Check out what more 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, ride aboard one of the trains from Windsor Station.
What's the seasonal weather like in Windsor?
The hottest months are usually July and August with an average temp of 62°F, while the coldest months are January and February with an average of 22°F. The snowiest months in Windsor are March, January, November, and February, with each month seeing an average of 15 inches of snowfall.