Photo by William E Berry Jr.

Windsor vacation rentals

We found 286 vacation rentals — enter your dates for availability

Discover a selection of 9 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.

Vacation rentals with weekly discounts - Windsor

Showing deals for:Nov 14 - Nov 21

Image gallery for Reading Farms Estate

Property grounds
10 out of 10 rating
Exceptional
(34 reviews)

Reading Farms Estate

Reading, VT

10% off
Price is CA $3,686
CA $31,982 total
includes taxes & fees
Reading Farms Estate

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Find out more about Windsor

Find out more about Windsor

Why visit Windsor

  1. Outdoor Activities: Enjoy a variety of adventures in Windsor's scenic landscapes, perfect for families and adventure seekers alike.
  2. Historic Bridges: Discover the charm of Windsor by exploring its unique historic bridges that showcase the town's rich heritage.
  3. Windsor Mansion Inn: Experience cozy accommodations at the Windsor Mansion Inn, ideal for a memorable stay.
  4. Shopping and Dining: Indulge in local shopping and delightful dining options in the friendly downtown atmosphere.
  5. National State Park: Visit the nearby national state park for stunning views and outdoor exploration.

Popular types of accommodation in Windsor

If you're planning a getaway to Windsor, you're in for a treat! Our vacation rentals offer a wide range of options, including houses, condos, and charming cabins. Whether you’re looking for a spacious Windsor house for the whole family or a cozy stay at the Windsor Mansion Inn, we have the perfect spot for you. Enjoy the fresh air on an outdoor patio while creating unforgettable memories in this beautiful city.

  • Houses: The top choice for visitors to Windsor, these homes offer a spacious and comfortable environment, ideal for families and groups.
  • Condos: A popular option for those seeking modern amenities and convenient locations, perfect for a hassle-free stay.
  • Cabins: For a true escape into nature, these rustic retreats provide a serene atmosphere amidst the beautiful landscape.
  • Cottages: Charming and quaint, these cottages are perfect for a cozy getaway with loved ones.
  • Apartments: A practical choice for solo travellers or couples, offering all the essentials for a comfortable stay.**

Top attractions in Windsor

Windsor, Vermont, is perfect for adventure seekers and families alike, offering a range of outdoor activities and cultural experiences. Explore historic bridges, visit the national state park, and discover the environmental centre. Whether you're keen on touring Windsor, enjoying an afternoon shopping spree, or simply soaking in the local scenery, there's something for everyone in this charming town.

  1. Blow-Me-Down Bridge: This historic bridge, located 805m from Windsor, offers a charming glimpse into the area's past. Its unique architecture and serene surroundings make it a perfect spot for a leisurely stroll and photography, embodying the local cultural vibes.
  2. Mount Ascutney: Just 6.4km away, Mount Ascutney is a haven for outdoor enthusiasts. Enjoy breathtaking scenery, hiking trails, and the thrill of adventure as you explore its natural beauty.
  3. Saint-Gaudens National Historic Site: Located 3.2km from Windsor, this site celebrates the work of renowned sculptor Augustus Saint-Gaudens. The rich cultural vibes and beautifully maintained gardens provide a tranquil atmosphere for art lovers and history buffs alike.

Things to do recommended for couples

For a romantic getaway in Windsor, explore the stunning slopes at Arrowhead Recreation Area, indulge in relaxation at The Strong House Spa, or take a scenic flight over the breathtaking landscape at Morningside Flight Park. These experiences promise adventure and tranquility for couples seeking a memorable escape.

Things to do recommended for families

In Windsor, families can explore the Upper Valley Aquatic Center for splashes of fun, visit Maple Lanes for arcade adventures, or unwind at Wilderness Trails for some relaxation. Each location offers a unique experience, perfect for creating lasting memories together.

Things to do recommended for groups

Experience the local charm of Windsor with a visit to Harpoon Brewery for some craft brews, explore the scenic Brownsville Trail for an outdoor adventure, and shop at The Sustainable Farmer for unique local goods. Enjoy the vibrant community vibes together!

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

When planning your trip, whether you're travelling with a group, family, pets, or looking for extended stays, it’s important to prioritise your preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Windsor with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor space for group get-togethers. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Windsor with young kids: Traveling with young kids can be quite the adventure. It's important to prioritize their comfort and safety, along with ensuring access to 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 fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windsor: If you're in search of vacation rentals offering great deals 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 Windsor

Windsor, Vermont, offers a delightful blend of adventure and charm, perfect for a memorable vacation. From exploring the scenic landscapes of Windsor County to enjoying the friendly atmosphere of downtown Windsor, visitors can indulge in outdoor activities and historical excursions. The town's family-friendly vibe and urban charm make it an ideal base for discovering nearby attractions, ensuring a rich and varied travel experience in this picturesque corner of New England.

  • Woodstock: Nestled 19.3km from Windsor, Woodstock is renowned for its stunning natural beauty and outdoor adventures. This charming city is perfect for those seeking a blend of excitement and relaxation, offering access to ski fields, resorts, and breathtaking landscapes. The picturesque surroundings include serene lakes, majestic mountains, and lush valleys, making it an ideal spot for hiking, skiing, and photography. Take a stroll through the quaint downtown area, where you'll find unique shops, delightful eateries, and local art galleries that reflect the region's cultural heritage.
  • Cornish: Located a mere mile from Windsor, Cornish is a delightful small town known for its stunning scenery and outdoor recreational opportunities. This idyllic spot is popular among adventurers who enjoy skiing and exploring the local ski fields and resorts. The town is surrounded by beautiful lakes and mountains, providing ample opportunities for hiking, fishing, and enjoying nature. Don't miss the opportunity to visit the historic Cornish-Windsor Covered Bridge, a charming landmark that offers a glimpse into the area's rich history.
  • Ascutney: Situated within the Windsor area, Ascutney is a quaint village that attracts visitors with its outdoor adventures and ski experiences. The village is home to ski resorts and fields, making it a hotspot for winter sports enthusiasts. Nearby, you can explore the striking mountains and lakes, as well as the expansive Ascutney State Park, perfect for hiking and picnicking. The local scenery offers a peaceful retreat, ideal for those looking to immerse themselves in nature's beauty while enjoying a variety of outdoor activities.

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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 hoping to save on your upcoming journey? Keep in mind that being flexible with your travel dates can lead to better prices, as they often vary. Additionally, opting for a longer stay typically allows for significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your travel. You can create new trips, resume your previous work, or review and manage your itinerary all in one place. Your saved or booked properties are neatly organized under categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-ca/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:

  • 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)
  • Sugarbush Farm (13.4 mi / 21.5 km)
  • Saskadena Six Ski Area (15 mi / 24.1 km)
  • Fox Run Golf Course (16.4 mi / 26.4 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)
  • Connecticut Lakes Region (13.4 mi / 21.5 km)
  • Perkins Pond (14.4 mi / 23.2 km)
  • Echo Lake (15.8 mi / 25.4 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 when booking a vacation rental?
When considering a vacation rental in Windsor, Vermont, the downtown area emerges as an excellent choice. This charming neighbourhood is not only picturesque but also conveniently located near several attractions that capture the essence of the town. Visitors can explore the historic architecture that lines the streets, including the iconic Old Constitution House, where the Vermont Constitution was adopted. Additionally, the nearby Windsor-Cornish Covered Bridge, a beautiful example of 19th-century engineering, offers a delightful spot for photographs and leisurely strolls.

In terms of vacation rentals, the downtown area boasts a variety of properties, suiting different preferences and budgets. You will find everything from quaint cottages to modern apartments, making it easy to find the great base for your stay. This central location allows easy access to local shops, restaurants, and community events, ensuring that you can immerse yourself fully in the vibrant local culture.
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 travelling 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.
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 those seeking ski resort rentals in Windsor, Vermont, the nearby Okemo Mountain Resort is the primary destination for winter sports enthusiasts. The town of Ludlow, just a short drive from Windsor, offers a variety of rental options, including cosy chalets and modern condos ideal for families or groups. Many of these properties come with essential amenities such as fully equipped kitchens, spacious living areas, and sometimes even fireplaces, great for unwinding after a day on the slopes.

In addition to Ludlow, the picturesque village of Windsor itself features charming options like historic homes and ski lodges that provide a warm atmosphere. Some of these accommodations may include features like outdoor decks, hot tubs, and easy access to local dining and shopping, enhancing the overall experience for travellers.
What is the most popular type of vacation rental accomodation in Windsor?
In Windsor, vacation houses, cabins, and cottages are all popular types of rental accommodations, with several options available in the area. These properties are typically situated in serene neighbourhoods, providing a tranquil escape amidst the picturesque Vermont landscape. Most vacation houses come equipped with spacious living areas, fully stocked kitchens, and outdoor spaces for relaxing, such as decks or patios that are superb for enjoying the fresh air. Cabins often feature rustic charm, with amenities like wood-burning stoves and large windows that showcase the surrounding nature. Cottages provide a cosy atmosphere, and many include charming details like fireplaces and quaint gardens.
Are there any family house rentals in Windsor?
In Windsor, Vermont, there are several family-friendly house rentals available, making it an inviting destination for groups. The area is known for its picturesque landscapes and proximity to recreational activities. Many properties in the vicinity offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and explore.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Windsor?
In Windsor, Vermont, there are several pet-friendly house rentals available for travellers looking to accommodate their furry companions. Many of these vacation homes feature amenities such as spacious gardens or yards, allowing pets to enjoy the outdoors. Inside, guests can expect comfortable living spaces with fully equipped kitchens, cosy lounges, and essential amenities such as Wi-Fi and laundry facilities.
Are there any remote work vacation rentals in Windsor?
In Windsor, Vermont, there are several vacation rentals that cater to remote work needs. These properties typically come equipped with essential amenities such as Wi-Fi, desks, ergonomic chairs, and even computer monitors, making them suitable for those needing to work from a comfortable environment. The charming town offers a picturesque backdrop, with nearby attractions like the historic Windsor Mansion and the scenic Connecticut River, providing a great blend of work and leisure. Travellers will find that many accommodations also feature comfortable living spaces and outdoor areas, ideal for unwinding after a productive day. 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 travellers 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 essential kitchen facilities, with many properties featuring microwaves, stovetops, and refrigerators. These amenities allow travellers to prepare their own meals, providing a convenient and cost-effective option during their stay. Additionally, cookware, dishware, and utensils are often available, ensuring guests have everything they need for dining in.
When is the best time to visit Windsor for a vacation rental?
July marks the most popular time to visit Windsor, Vermont, as the peak season runs from July to September. During this vibrant summer period, the charming town comes alive with outdoor activities, including hiking and exploring the picturesque countryside. The warm weather, typically ranging from the mid-teens to low twenties Celsius, allows for comfortable days spent enjoying nature and taking in the scenic beauty of the Green Mountains.

Visitors flock to Windsor in July to partake in local events and festivals, creating a lively atmosphere filled with opportunities to connect with fellow travellers. The abundance of outdoor adventures, such as kayaking on the Connecticut River or strolling through the lush landscapes, makes this a fantastic time for those seeking both relaxation and excitement.

For those looking for a more budget-friendly option, consider visiting in December. This quieter month offers the chance to embrace the serene beauty of Windsor blanketed in snow, superb for winter sports enthusiasts or anyone wanting a peaceful retreat. It's a wonderful time to experience the charm of the town during the vacation season, with festive decorations adding to its allure.
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.
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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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