Windsor vacation rentals

Why visit Windsor

1. Scenic Outdoor Adventures: Windsor offers breathtaking lakes, parks, and ski resorts, perfect for nature lovers.
2. Charming Atmosphere: Experience the friendly locals and family-friendly environment that make Windsor unique.
3. Rich History: Explore nearby municipalities to delve into Vermont's fascinating historical background.
4. Diverse Accommodations: Choose from cozy condos, spacious homes, or rustic cabins tailored to your vacation needs.
5. Year-Round Activities: Enjoy skiing in winter and relaxing nature strolls or hiking during warmer months.

Popular types of accommodation in Windsor

Discover the perfect vacation rental in Windsor with a variety of options tailored to your needs. Whether you prefer a cozy condo, a spacious private vacation home, or a comfortable apartment, Windsor has something for everyone. From budget-friendly accommodations to upscale hotels, our platform ensures transparency and savings for your stay. Explore Windsor Village and beyond, and find the ideal spot to unwind and enjoy your getaway.

• Condos: A favored choice for travelers, condos in Windsor offer modern amenities and convenient locations, perfect for a relaxing getaway.
• Houses: Ideal for families or groups, these homes provide spacious living and the comforts of home during your stay.
• Apartments: Cozy and practical, apartments are great for couples or solo travelers seeking a central base in Windsor.
• Cabins: For a rustic experience, cabins provide a charming retreat surrounded by nature, perfect for outdoor enthusiasts.
• Cottages: Quaint and inviting, cottages in Windsor offer a cozy atmosphere for a peaceful escape.**

Top attractions in Windsor

Windsor, Vermont is perfect for outdoor and adventure enthusiasts, offering a mix of scenic lakes, national and state parks, and ski resorts. Visitors can enjoy a range of cultural and outdoor experiences, making it an ideal vacation spot. For those planning their stay, checking out reviews of local hotels can enhance your trip, ensuring you find the perfect place to unwind after a day of exploration.

1. Blow-Me-Down Bridge: This historic bridge, located half a mile from Windsor, offers a charming glimpse into the area's architectural heritage. Surrounded by scenic beauty, it provides a perfect spot for photography and enjoying the local culture.
2. Mount Ascutney: Situated four miles away, Mount Ascutney is a haven for adventure seekers. With its hiking trails and stunning vistas, it invites outdoor enthusiasts to explore its natural beauty and enjoy breathtaking scenery.
3. Saint-Gaudens National Historic Site: Just two miles from Windsor, this historic site celebrates the works of sculptor Augustus Saint-Gaudens. Visitors can immerse themselves in art, history, and beautiful landscapes, making it a cultural gem.

Things to do recommended for couples

For a romantic getaway in Windsor, explore Okemo Mountain Resort for skiing adventures, unwind at The Strong House Spa for ultimate relaxation, and soar above the landscape with a scenic flight at Morningside Flight Park. Each experience offers unique vibes for couples seeking memorable moments together.

Things to do recommended for families

While in Windsor, Vermont, families can splash around at the Upper Valley Aquatic Center, enjoy arcade fun at Maple Lanes, or unwind at Wilderness Trails for wellness and relaxation. Each destination offers a unique experience just a short drive away, perfect for family bonding.

Things to do recommended for groups

Groups visiting Windsor, Vermont can enjoy a tour at Harpoon Brewery for a fun and entertaining experience. Hiking the Brownsville Trail offers beautiful outdoor scenery, while The Sustainable Farmer provides unique local products for guests to explore and enjoy.

What do I need to keep in mind when booking a vacation in Windsor

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to consider.

• Traveling to Windsor with a group: Think about how many bedrooms you require, as well as any amenities like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options, and more, on Vrbo.
• Traveling to Windsor with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
• Taking your pets with you to Windsor: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that your whole family feels comfortable and at home.
• Planning for a long term stay visiting Windsor: If you're searching for vacation rentals that offer great deals for month-long stays or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Windsor

Windsor, Vermont, is a hidden gem for outdoor enthusiasts and adventure seekers. Nestled in a picturesque setting, this charming town offers a family-friendly atmosphere and friendly locals. Explore nearby municipalities for a taste of Vermont's rich history and scenic beauty. Whether you're hitting the slopes or enjoying a relaxing stroll through nature, Windsor promises an unforgettable experience filled with luxury and warmth. Don't miss the chance to discover what makes Vermont truly special!

• Woodstock: Located 12 miles from Windsor, Woodstock is a picturesque town renowned for its charming New England ambiance and outdoor adventures. Visitors flock to Woodstock for its excellent skiing and outdoor activities, with access to nearby ski resorts and fields. The town is surrounded by stunning natural landscapes, including serene lakes, majestic mountains, and lush parks, making it a perfect destination for nature lovers. Explore the quaint downtown area, which features unique shops, art galleries, and delightful eateries, offering a warm welcome and a taste of local culture.
• Killington: Situated 24 miles from Windsor, Killington is a hub for adventure enthusiasts, particularly those seeking thrilling ski experiences. Known for its expansive ski field and resort, it attracts winter sports lovers from all over. The breathtaking mountainous terrain and picturesque valleys provide stunning backdrops for outdoor activities year-round, including hiking and biking in the warmer months. After an exhilarating day on the slopes, unwind at local eateries and enjoy the vibrant après-ski scene that Killington has to offer.
• Cornish: Just 1 mile from Windsor, Cornish is a quaint, scenic town that offers a peaceful retreat for outdoor enthusiasts and sightseers alike. With its close proximity to Windsor, it’s an ideal spot for quick getaways. Visitors can enjoy skiing at local fields, exploring recreational areas, and taking in the beautiful surrounding landscapes, which include serene lakes and impressive mountains. The town is also home to the iconic Cornish-Windsor Covered Bridge, perfect for a memorable photo opportunity and a glimpse into the area's rich history.

Best time to go to Windsor

If you're planning a trip to Windsor, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like February, May and December tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	16.7°F (-8.5°C)	Light Rain	Mostly Cloudy	Average	Moderately High
February	18.9°F (-7.3°C)	Light Rain	Mostly Cloudy	Slightly Low	Moderately High
March	27.1°F (-2.7°C)	Light Rain	Mostly Cloudy	Average	Average
April	39.4°F (4.1°C)	Light Rain	Mostly Cloudy	Average	Moderately Low
May	52.3°F (11.3°C)	Light Rain	Mostly Sunny	Slightly Low	Moderately 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	Moderately Low
October	45.5°F (7.5°C)	Light Rain	Mostly Cloudy	Average	Average
November	33.1°F (0.6°C)	Light Rain	Mostly Sunny	Average	Average
December	24.3°F (-4.3°C)	Light Rain	Mostly Cloudy	Slightly Low	Moderately High

Booking with Vrbo is simple

Are you interested in getting the best deal for your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To help you find a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to support you in finding the perfect getaway!

Save more with One Key

Secure an eligible Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner has its rewards! By joining our travel rewards program, One Key, you can immediately access exclusive member savings and earn or use OneKeyCash™ on qualifying bookings. Sign up today and begin enjoying the savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily create new trips, resume planning from where you last stopped, or organize your travel plans. You can view your saved or booked properties, sorted into categories like Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.