Windsor Vacation Packages

Things to do in and around Windsor

Windsor, Vermont, is an ideal destination for adventure enthusiasts and outdoor lovers. With its renowned ski resorts and fields, visitors can enjoy thrilling winter sports. Additionally, Windsor offers family outings and is perfect for a relaxing beach vacation. Whether you're seeking an exhilarating break or a peaceful escape, Windsor has something for everyone to enjoy in the great outdoors.

Shopping

In Windsor, visit The Sustainable Farmer for unique gifts. For a bit of a drive, head to Quechee Gorge Village, 17.7km away, for charming shops and souvenirs. Closer by, North Country Smokehouse, just 11.3km from Windsor, offers local delicacies perfect for gifts.

Recreation

The Upper Valley Aquatic Center, located 17.7km from Windsor, offers a family-friendly atmosphere with a variety of aquatic activities. Nearby, the Woodstock Town Hall Theatre presents cultural and romantic performances, while the Woodstock Country Club provides a scenic golf course for outdoor sports enthusiasts.

Adventure

Explore the scenic Brownsville Trail for a refreshing outdoor experience in Windsor. Enjoy skiing and snowboarding at Arrowhead Recreation Area, located 14.5km from Windsor, or unleash your competitive spirit at Maple Lanes, an exciting arcade adventure zone situated 12.9km away, perfect for family fun.

Nightlife

Windsor offers a charming nightlife with cozy pubs and local eateries. Visit the Harpoon Brewery for craft beers and tasty bites, then head to the Windsor Station for live music and a vibrant atmosphere. Enjoy the friendly vibe and meet locals while soaking in the evening's excitement.

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

Find the best attractions near Windsor

Windsor, Vermont, is an ideal destination for adventure seekers and outdoor enthusiasts, offering a blend of historic sites, national parks, and environmental centres. Visitors can enjoy cultural experiences and family-friendly activities, while also exploring local attractions such as vacation rental resorts and seasonal festivals. Don't miss the chance to experience the charm of nearby landmarks, including Windsor Island and the renowned Windsor Castle, making it a perfect getaway for all types of travellers.

• Blow-Me-Down Bridge: This historic bridge, located 805m from Windsor, offers a charming glimpse into the area’s rich cultural heritage. Its picturesque setting and unique architecture make it a perfect spot for photography and leisurely walks, allowing visitors to appreciate the local history.
• Mount Ascutney: Just 6.4km away, Mount Ascutney is a haven for outdoor enthusiasts. With breathtaking scenery, hiking trails, and opportunities for adventure sports, this mountain provides a thrilling escape into nature, ideal for both seasoned adventurers and casual hikers.
• Saint-Gaudens National Historic Site: Located 3.2km from Windsor, this historic site celebrates the life and work of renowned sculptor Augustus Saint-Gaudens. Visitors can explore stunning sculptures and beautiful gardens, immersing themselves in the artistry and culture of the period.

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 with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	16.7°F (-8.5°C)	Light Rain	Mostly	Average	Average
February	18.9°F (-7.3°C)	Light Rain	Mostly	Slightly Low	Slightly High
March	27.1°F (-2.7°C)	Light Rain	Mostly	Average	Average
April	39.4°F (4.1°C)	Light Rain	Mostly	Average	Slightly Low
May	52.3°F (11.3°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
June	59.9°F (15.5°C)	Light Rain	Mostly Sunny	Average	Average
July	65.8°F (18.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	45.5°F (7.5°C)	Light Rain	Mostly	Average	Slightly High
November	33.1°F (0.6°C)	Light Rain	Mostly Sunny	Average	Slightly Low
December	24.3°F (-4.3°C)	Light Rain	Mostly	Slightly Low	Slightly High

Tips to save on your trip to Windsor

• Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Windsor.
• Consider traveling to Windsor during the low season (April to May and November) for more affordable options.
• Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
• Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.