Windsor holiday lettings

We found 309 holiday rentals — enter your dates for availability

Discover a selection of 12 homes and other holiday rentals in Windsor that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a pool. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Windsor

Showing deals for:10 Jul - 17 Jul

Image gallery for Reading Farms Estate

Property grounds
10 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)

Reading Farms Estate

Reading

8% off
Price is £22,031
for 7 nights, 1 home
£3,147 per night
includes taxes & fees
Reading Farms Estate

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The lush setting of Windsor is ready to explore

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

Activities and attractions in Windsor

Are you hoping to find attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Windsor a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 looking for fun outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Windsor. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Travelling to and around Windsor

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

If you'd prefer to travel by train, the main station serving the city is Windsor Station.

Frequently asked questions

What is the best area to stay in Windsor when booking a holiday rental?
When considering a holiday rental in Windsor, Vermont, the charming neighbourhoods surrounding the town centre are particularly appealing. Windsor boasts a quaint atmosphere with a mix of historical architecture and natural beauty. One of the most attractive areas is near the Connecticut River, which not only offers picturesque views but also provides opportunities for scenic walks and outdoor activities.

In this area, you can easily access top attractions like the historic Windsor Mansion and the nearby Cornish-Windsor Covered Bridge, which is one of the longest wooden covered bridges in the United States. The town features a variety of properties, ranging from cosy cottages to more spacious homes, suiting different preferences and group sizes. The overall selection tends to be quite diverse, making it easy to find the great fit for your stay.

Additionally, Windsor's vibrant local community and its proximity to other attractions in the Upper Valley region make it an ideal base for exploring the beautiful Vermont landscape.
How much does it cost to rent a holiday home in Windsor?
Prices for holiday 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 holiday 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 near Windsor, Vermont, the nearby Okemo Mountain Resort is a prime destination for winter sports enthusiasts. In the charming town of Ludlow, just a short drive from Windsor, visitors can find a range of rental options, including cosy chalets and spacious condos. Many of these properties offer amenities such as ski-in/ski-out access, fully equipped kitchens for convenient meal preparation, and living areas with fireplaces to unwind after a day on the slopes.

In Ludlow, you'll also discover properties with additional perks like hot tubs and game rooms, making them great for families or groups looking to enjoy après-ski activities. The town itself features a variety of local shops, restaurants, and bars, providing a vibrant setting for visitors.

For those interested in exploring the surrounding area, the scenic Green Mountains offer numerous hiking trails and beautiful landscapes to enjoy year-round.
What is the most popular type of holiday rental accomodation in Windsor?
In Windsor, holiday houses are the most popular type of holiday rental, with around 18 available throughout the area. These properties typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also feature outdoor spaces, such as decks or gardens, where guests can relax and enjoy the scenic surroundings. Additionally, there are about 10 cabins and several cottages, which provide a more rustic charm and often include amenities like fireplaces and proximity to nature trails.
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 those travelling with children. The area features charming homes that often include spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas where kids can play and explore. Many properties also offer amenities like Wi-Fi and laundry facilities, ensuring a comfortable stay for all.

Visitors can enjoy nearby attractions such as the picturesque Windsor Village, which is steeped in history, and the scenic banks of the Connecticut River, superb for outdoor activities. Moreover, the proximity to local parks and nature trails provides ample opportunities for family adventures, whether it's hiking, biking, or simply enjoying a picnic.
Can I rent a holiday home with a pool or hot tub in Windsor?
In Windsor, Vermont, there are several holiday homes available for rent that come equipped with pools or hot tubs, making it a delightful choice for travellers seeking relaxation. The town is located along the banks of the Connecticut River and is surrounded by picturesque landscapes, presenting a charming backdrop for your stay.

Many of the available rentals feature amenities such as private pools, hot tubs, and spacious outdoor areas, ideal for enjoying the serene environment. Inside, you can expect well-appointed living spaces, fully equipped kitchens for self-catering, and comfortable bedrooms designed for a restful night's sleep.

Windsor's proximity to outdoor activities, including hiking and biking trails, enhances the appeal of these properties, allowing guests to enjoy both leisure and adventure during their holiday.
Can I find long-stay holiday rentals in Windsor?
A long-stay holiday 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 those looking to enjoy a getaway with their furry companions. Many of these accommodations come with amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely.

The town is surrounded by beautiful natural scenery, making it ideal for outdoor activities with pets, including hiking and exploring the nearby Green Mountains. Additionally, Windsor is close to the Connecticut River, providing opportunities for leisurely walks along the waterfront.
Are there any remote work holiday rentals in Windsor?
In Windsor, Vermont, there are numerous remote work holiday rentals available, with around 26 options to choose from. This quaint town offers a peaceful environment ideal for those looking to balance work and leisure. Many of the properties feature dedicated workspaces, including desks and ergonomic chairs, as well as essential amenities such as high-speed Wi-Fi, which is crucial for remote work.

Travellers can expect comfortable living arrangements, often with fully equipped kitchens for preparing meals during extended stays. The scenic surroundings of Windsor provide opportunities for outdoor activities, making it easy to unwind after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Windsor holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 rental amenities typically include kitchens, making it convenient for guests to prepare their own meals. Many properties also allow pets, which is a significant advantage for those travelling with furry companions. Onsite parking is commonly available, ensuring easy access for guests with vehicles. Additionally, you'll often find coffee and tea makers in the rentals, allowing for a comforting start to the day. Dining areas are also standard, providing a pleasant space for guests to enjoy their meals together.
When is the best time to visit Windsor for a holiday rental?
The best time to visit Windsor, Vermont, for a holiday rental is during the peak season from July to September. This vibrant period attracts visitors keen on enjoying the lush greenery and numerous outdoor activities that the region has to offer. With warm temperatures averaging around 20 to 25 degrees Celsius, this is an ideal time for hiking, biking, and exploring the charming local attractions.

July stands out as the most popular month, where you can immerse yourself in the lively option of summer festivals and events. Families and adventure seekers alike love this time for its abundance of activities, from kayaking on the Connecticut River to leisurely strolls through picturesque parks. The scenic beauty of Windsor, complete with its historic architecture and stunning landscapes, is truly captivating.

If you're looking for a more budget-friendly option, consider planning your visit in December. Although it falls outside the peak season, this month offers a unique charm with the onset of winter, presenting opportunities for cosy getaways and festive celebrations. You can enjoy the tranquillity of the snowy landscape while indulging in warm, comforting activities.

Ultimately, your choice will depend on whether you prefer the bustling energy of summer or the serene beauty of winter.
How early should I book a Windsor holiday rental?
Book your Windsor holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Windsor?
In Windsor, Vermont, visitors can explore a variety of charming attractions that reflect the town's rich history and natural beauty. The historic downtown area features beautifully preserved buildings and a selection of local shops and cafes, making it a pleasant spot for a leisurely stroll. The nearby Simon Pearce Glassblowing Studio offers a great experience where guests can watch artisans create stunning glass pieces, and the attached restaurant provides a lovely dining option with views of the Ottauquechee River.

For those who enjoy the outdoors, Mount Ascutney State Park is a short drive away, offering hiking trails with breathtaking views and opportunities for picnicking. The park is particularly popular in the fall when the foliage transforms into a vibrant display of colours. Additionally, the Windsor-Cornish Covered Bridge, one of the longest covered bridges in the country, is a picturesque landmark worth visiting, providing excellent photo opportunities and a glimpse into the region's history.
Can I change or cancel my Windsor home rental booking on Vrbo?
To find Windsor holiday 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 cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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