Windsor vacation rentals

We found 304 vacation rentals — enter your dates for availability

Discover a selection of 12 homes and other vacation rentals in Windsor that are perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the amenities you expect for your stay, including WiFi and parking. No matter what you're looking for, you'll be able to choose a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about Windsor

Why visit Windsor

  • Outdoor Adventures: Windsor offers a plethora of outdoor activities, including skiing and exploring nearby parks, perfect for adventure seekers.
  • Scenic Beauty: The town boasts stunning natural landscapes, ideal for those looking to relax and enjoy the great outdoors.
  • Charming Small Town: Discover the quaint streets of Windsor, reflecting its rich history and warm community atmosphere.
  • Vacation Rentals: A variety of cozy accommodations, from rustic cabins to charming homes, ensure a comfortable stay.
  • Historical Excursions: Venture into nearby New Hampshire for unique historical sites and experiences.

Popular types of accommodation in Windsor

If you’re planning a getaway to Windsor, Vermont, you’ll find a variety of popular vacation rental options to suit your needs. Choose from charming houses, cozy condos, and rustic cabins that offer comfort and convenience. Whether you’re looking for apartments in Windsor County or homes for rent, our selection ensures you have a memorable stay in this beautiful region. Explore Windsor’s hidden gems and enjoy a relaxing retreat.

  • Houses: These spacious homes are the top choice for travelers seeking comfort and privacy while enjoying their stay in Windsor.
  • Condos: Ideal for those wanting a blend of home-like amenities and hotel-style services, condos are a popular option in Windsor.
  • Cabins: Embrace the rustic charm of Windsor by staying in a cozy cabin surrounded by nature.
  • Cottages: Quaint and inviting, cottages offer a perfect retreat for couples and families alike.
  • Apartments: Convenient and flexible, apartments are a great choice for travelers looking for a home base in Windsor.**

Top attractions in and around Windsor

Windsor, Vermont, is perfect for outdoor enthusiasts and adventure seekers, offering a variety of activities for family and culture lovers alike. Key attractions include medical centers, parks, and national/state parks, providing ample opportunities for exploration and outdoor fun. Whether you're skiing or simply enjoying the natural beauty, Windsor has something to captivate every visitor.

  • Mt Ascutney Hospital and Health Center: Primary Care - Windsor: This medical center offers a welcoming atmosphere focused on family health and wellness. It's a community hub providing essential healthcare services and fostering a sense of connection among residents.
  • American Precision Museum: Dive into the rich history of American manufacturing at this engaging museum. It showcases the evolution of precision tools and machinery, blending culture and innovation in a captivating setting.
  • Quechee Gorge Bridge: Experience the thrill of standing atop this stunning bridge, which offers breathtaking views of the gorge below. Perfect for outdoor enthusiasts, it's an ideal spot for hiking and photography amidst nature's beauty.

Things to do recommended for couples

Windsor, Vermont, offers charming experiences for couples, such as a romantic walk along the Connecticut River or exploring the picturesque streets filled with historic architecture. Don't miss a cozy dinner at a local restaurant, followed by a sunset view at the nearby Mount Ascutney.

Things to do recommended for families

Families will love exploring the beautiful trails at Mount Ascutney State Park, where hiking and picnicking await. The nearby Simon Pearce Glassblowing Studio offers a unique glimpse into artisan craftsmanship, perfect for all ages to enjoy.

Things to do recommended for groups

Groups visiting Windsor, Vermont can enjoy a scenic hike along the Connecticut River, explore local art galleries, and participate in a craft workshop at a nearby studio, ensuring a memorable experience filled with community spirit and creativity.

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

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, or pets, or if you're considering extended stays, be sure to prioritize your needs using the right filters. Here are some helpful booking tips for Vrbo.

  • Traveling to Windsor with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Windsor with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windsor: For many families, a trip isn't truly complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windsor: If you're searching for vacation rentals that offer discounts for stays of a month 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 and around Windsor

Windsor, Vermont, offers a charming blend of outdoor adventures and scenic beauty, perfect for a family-friendly getaway. Explore the quaint streets of this small town and venture into nearby New Hampshire for historical excursions and friendly vibes. With opportunities for skiing and outdoor activities, Windsor invites travelers to immerse themselves in its rich atmosphere and discover the warmth of its community.

  • Woodstock: Located 12 miles from Windsor, Woodstock is a quintessential Vermont town renowned for its outdoor adventures and charming New England atmosphere. Visitors flock here for skiing, with access to excellent ski fields and resorts, making it a popular winter destination. In addition to winter sports, the town offers beautiful landscapes, including scenic lakes and majestic mountains. The nearby Marsh-Billings-Rockefeller National Historical Park is a must-visit, providing trails for hiking and a glimpse into the area's rich history.
  • Cornish: Just 1 mile away from Windsor, Cornish is a small town that offers abundant outdoor activities and a welcoming community feel. Much like Woodstock, Cornish is a great spot for skiing and adventure seekers, with ski fields and resorts nearby. The picturesque landscape features stunning lakes and rolling mountains, perfect for year-round exploration. Don't miss the chance to visit the Cornish-Windsor Covered Bridge, one of the longest covered bridges in the United States, which is a charming and historic landmark.
  • Ascutney: Situated within the Windsor area, Ascutney is a quaint village that serves as an adventure hub for outdoor enthusiasts. With easy access to ski fields and resorts, it’s an ideal destination for skiing and winter sports lovers. The village is enveloped by beautiful mountains and serene lakes, providing ample opportunities for hiking, fishing, and enjoying nature. Ascutney State Park offers trails with stunning views, making it a prime location for outdoor activities throughout the year.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January16.7°F (-8.5°C)Light RainMostly CloudyAverageModerately High
February18.9°F (-7.3°C)Light RainMostly CloudySlightly LowModerately High
March27.1°F (-2.7°C)Light RainMostly CloudyAverageAverage
April39.4°F (4.1°C)Light RainMostly CloudyAverageModerately Low
May52.3°F (11.3°C)Light RainMostly SunnySlightly LowModerately 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 HighModerately Low
October45.5°F (7.5°C)Light RainMostly CloudyAverageAverage
November33.1°F (0.6°C)Light RainMostly SunnyAverageAverage
December24.3°F (-4.3°C)Light RainMostly CloudySlightly LowModerately High

Booking with Vrbo is simple

Are you aiming to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and vacation rental type. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo's Trip Board is designed to help you plan your travel effortlessly. You can create new trips, keep your plans moving forward, or review and organize your existing bookings all in one place. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips for easy access. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The lush setting of Windsor is ready to explore

The forests, mountains and countryside are a perfect backdrop to your vacation home in Windsor. Travelers to this scenic city praise the golfing, hiking and bird watching. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Windsor

Do you want to find attractions to see during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Windsor a one-of-a-kind vacation spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Arrowhead Recreation Area (8.7 mi / 14.1 km)
  • Quechee State Park (11 mi / 17.7 km)
  • Upper Valley Aquatic Center (11.4 mi / 18.3 km)
  • Quechee Ski Hill (12.7 mi / 20.5 km)
  • Whaleback Mountain (13 mi / 20.9 km)
  • Sugarbush Farm (13.4 mi / 21.5 km)

Exploring the natural features in Windsor

Whether you're an active traveler or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Windsor. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Mount Ascutney (4.2 mi / 6.8 km)
  • Quechee Gorge Bridge (10.9 mi / 17.6 km)
  • Marsh-Billings-Rockefeller National Historical Park (13.1 mi / 21.1 km)
  • Echo Lake (15.8 mi / 25.4 km)
  • Northern Rail Trail (15.9 mi / 25.6 km)
  • Amherst Lake (15.9 mi / 25.7 km)

Traveling to and around Windsor

The nearest airport is in Lebanon, NH (LEB-Lebanon Municipal), located 10.7 mi (17.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Springfield, VT (VSF-Hartness State), which is 11.7 mi (18.8 km) away.

If you're traveling by train, the main station is Windsor Station.

Frequently asked questions

What is the best area to stay in Windsor, Vermont, United States of America when booking a vacation rental?
When considering a vacation rental in Windsor, Vermont, the downtown area stands out as a fantastic option. This charming neighborhood is not only quaint but also conveniently located near several attractions that make your stay enjoyable. You can explore the picturesque banks of the Connecticut River, great for leisurely walks or picnics. Don't miss the chance to visit the historic Old Constitution House, where you can learn about Vermont's intriguing history.

Another delightful option is the area surrounding the Windsor-Cornish Covered Bridge, which is renowned for its scenic beauty and is a great spot for photography enthusiasts. This bridge is one of the oldest covered bridges in the country and adds a touch of charm to your stay.
How much does it cost to rent a vacation home in Windsor?
Prices for vacation rentals in Windsor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windsor to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Windsor vacation house rentals?
You can find great discounts on house rentals in Windsor on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Windsor ski resort rentals?
For the best ski resort rentals near Windsor, Vermont, travelers should consider the nearby Okemo Mountain Resort, located just a short drive away. The area around Ludlow, which is close to Okemo, offers a variety of vacation rentals ranging from cozy cabins to spacious condos. Many of these properties come equipped with essential amenities like fully stocked kitchens, fireplaces, and ski storage, making them ideal for families or groups looking to enjoy a ski getaway.

In Ludlow, visitors can find convenient access to local dining options and shops, enhancing the overall experience. Rentals often feature additional perks such as hot tubs, game rooms, or access to community amenities like pools and fitness centers. This area is not only great for skiing but also offers opportunities for snowshoeing and winter hiking.

For those seeking a more tranquil setting, the surrounding areas of Mount Holly or Chester provide charming rural homes and historic inns. These accommodations typically feature rustic décor and may include outdoor spaces for enjoying the beautiful Vermont landscape. Proximity to cross-country skiing trails and winter festivals adds to the allure of the region, ensuring that visitors have a memorable experience both on and off the slopes.
What is the most popular type of vacation rental accomodation in Windsor?
In Windsor, vacation houses, cabins, and cottages are the most popular types of rental accommodations, with several options available in this charming town. These properties typically feature cozy interiors with multiple bedrooms, fully equipped kitchens, and inviting living spaces, making them ideal for families or groups looking to enjoy the area's natural beauty. Many rentals have outdoor areas, such as decks or patios, where guests can relax and take in the scenic surroundings.
Are there any family house rentals in Windsor?
In Windsor, Vermont, there are several family-friendly vacation rentals available. This charming town offers a variety of homes that can accommodate families, featuring spacious living areas and full kitchens, superb for preparing meals together. Many properties also include outdoor spaces, which are great for kids to play and enjoy the fresh air.

Visitors can explore local attractions such as the beautiful Mount Ascutney, where outdoor activities like hiking and nature walks are plentiful. Additionally, the nearby Connecticut River provides opportunities for scenic views and family outings.
Can I rent a vacation home with a pool or hot tub in Windsor?
In Windsor, Vermont, there are several vacation homes available for rent that feature pools and hot tubs. This charming town offers a picturesque setting along the banks of the Connecticut River, making it an attractive destination for travelers looking to relax and enjoy outdoor activities. Many of the rentals include amenities such as private pools, hot tubs, and spacious outdoor areas, ideal for family gatherings or peaceful retreats. Additionally, fully equipped kitchens and comfortable living spaces are common, allowing guests to unwind after a day of exploring the scenic surroundings. Find your rental in Windsor with a pool or a hot tub.
Can I find long-stay vacation rentals in Windsor?
A long-stay vacation rental in Windsor is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Windsor?
In Windsor, Vermont, there are several pet-friendly house rentals available, offering a welcoming environment for travelers with furry companions. Many of these vacation homes come equipped with amenities such as spacious yards, cozy living areas, and fully stocked kitchens, making them ideal for families or groups seeking a comfortable stay.

The area is known for its beautiful landscapes and outdoor activities, with nearby parks and recreational areas providing opportunities for walks and hikes with pets. Windsor's charm extends to its quaint downtown, where you'll find local shops and eateries that often welcome pets.
Are there any remote work vacation rentals in Windsor?
In Windsor, Vermont, there are some great options for remote work vacation rentals, with around 13 available throughout the area. Travelers can expect properties equipped with amenities that support a productive work environment, including free Wi-Fi in rooms and public areas, ensuring connectivity for work-related tasks. Many rentals offer comfortable living spaces conducive to both relaxation and productivity, often featuring separate work areas or desks.

Windsor is rich in history and charm, with nearby attractions such as the Windsor-Cornish Covered Bridge and Mount Ascutney State Park, which provide opportunities for outdoor activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Windsor vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Windsor with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Windsor?
In Windsor, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals and enjoy family dining experiences. Many rentals also permit pets, making it easier for travelers to bring their furry companions along. Onsite parking is commonly available, providing convenience for those who drive. Additionally, rentals often feature coffee and tea makers, great for enjoying a warm beverage in the morning.
When is the best time to visit Windsor for a vacation rental?
The best time to visit Windsor for a vacation rental is during the peak season from July to September, when the vibrant setting and warm temperatures create an inviting setting for outdoor adventures. July, in particular, stands out as the most popular month, attracting travelers eager to enjoy the lush landscapes and activities that Windsor has to offer.

During these summer months, temperatures typically range from the mid-60s to the low 80s Fahrenheit, making it ideal for exploring the picturesque Connecticut River and nearby hiking trails. Visitors can partake in activities such as kayaking, biking, and enjoying the local parks, allowing for plenty of opportunities to soak in the natural beauty of the area.

For those looking for a more budget-friendly option, consider visiting in December. While this is the low season, it offers a unique charm with the chance to experience winter activities and cozy accommodations. The festive atmosphere during the holiday season can be quite delightful, providing a chance to enjoy the local culture in a quieter setting.

Ultimately, whether you prefer the lively summer months filled with outdoor fun or the peaceful winter charm, Windsor has something to offer every traveler.
How early should I book a Windsor vacation rental?
Book your Windsor vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Windsor, Vermont, United States of America?
In Windsor, Vermont, visitors can enjoy a variety of attractions that highlight the area's natural beauty and rich history. The historic downtown features charming architecture and local shops, superb for leisurely strolls. Nearby, the Connecticut River offers opportunities for kayaking and fishing, with scenic views of the surrounding landscape.

The Simon Pearce Glassblowing Factory, located just a short drive away in Quechee, provides a fascinating glimpse into the art of glassblowing and features a beautiful restaurant with views of the river. Additionally, the nearby Mount Ascutney State Park offers hiking trails and stunning vistas, making it a great spot for outdoor enthusiasts.

The Windsor-Cornish Covered Bridge, one of the longest wooden covered bridges in the United States, is also a must-see. It serves as an iconic symbol of the area's history and provides picturesque photo opportunities.
Can I change or cancel my Windsor home rental booking on Vrbo?
To find Windsor vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Windsor vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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