Photo by William E Berry Jr.

Windsor holiday lettings

We found 284 holiday rentals — enter your dates for availability

Discover a selection of 10 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:16 Jan - 23 Jan

Image gallery for Reading Farms Estate

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

Reading Farms Estate

Reading, VT

8% off
Price is £22,932
for 7 nights, 1 home
£3,276 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

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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:

  • 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)
  • Saskadena Six Ski Area (15 mi / 24.1 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)
  • Connecticut Lakes Region (13.4 mi / 21.5 km)
  • Echo Lake (15.8 mi / 25.4 km)
  • Northern Rail Trail (15.9 mi / 25.6 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 downtown area is an excellent choice. This charming neighbourhood offers a delightful blend of local culture and easy access to various attractions. Staying here, you'll find yourself just a short stroll from the picturesque Windsor Village Historic District, where you can admire well-preserved 19th-century architecture and enjoy the quaint atmosphere. The area is also home to the famous Simon Pearce Glassblowing Factory, where visitors can watch artisans at work and shop for exquisite handcrafted glassware.

Another appealing option is the vicinity around the Connecticut River. This area not only provides stunning views and opportunities for outdoor activities such as kayaking and hiking but also boasts a few lovely parks and walking trails. Here, you can immerse yourself in the natural beauty of Vermont while being close to local shops and eateries.
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 ski resort rentals near Windsor, Vermont, travellers should look towards the nearby Okemo Mountain Resort, located just a short drive away. The area around Ludlow, which is the closest town to Okemo, offers a variety of rental properties, including cosy chalets and spacious condos. Many of these accommodations come with amenities such as fully equipped kitchens, fireplaces, and some even feature hot tubs, making them great for relaxing after a day on the slopes.

In addition to Ludlow, the charming village of Woodstock, located a bit further north, also provides excellent rental options. Here, visitors can find beautifully restored historic homes and modern cabins, often equipped with comfortable living areas, outdoor spaces, and proximity to local dining and shopping. The peaceful surroundings of Woodstock offer a picturesque setting, with easy access to cross-country skiing and snowshoeing trails.
What is the most popular type of holiday rental accomodation in Windsor?
In Windsor, the most popular types of holiday rental accommodations are holiday houses, cabins, and cottages, with several options available in this charming town. These rentals are often situated in picturesque settings, allowing guests to enjoy the scenic beauty of the Vermont landscape. Most properties feature amenities such as fully equipped kitchens, cosy living areas, and outdoor spaces where visitors can relax and take in the fresh air. For those looking for a rustic experience, cabins typically provide a warm, inclusive setting with wood-burning stoves and often include access to hiking trails or nearby rivers. Cottages offer a quaint, home-like feel, great for couples or small families seeking a peaceful getaway.
Are there any family house rentals in Windsor?
In Windsor, Vermont, there are several family-friendly house rentals available that cater to those travelling with children. The area features charming homes that often come with spacious living areas, fully equipped kitchens, and outdoor spaces great for family gatherings. Many properties also provide amenities such as Wi-Fi and laundry facilities for added convenience.
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 travelling with their furry companions. The area offers a selection of charming homes that often come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces for pets to enjoy. Many of these properties are set in peaceful surroundings, providing a tranquil retreat for both humans and animals alike.
Are there any remote work holiday rentals in Windsor?
In Windsor, Vermont, there are several remote work-friendly holiday rentals available, making it an excellent choice for those looking to combine work with leisure. Many of these properties offer dedicated workspace amenities such as desks, desk chairs, and computer monitors, alongside reliable Wi-Fi to ensure a productive environment. 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 holiday 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 holiday rental?
The most popular time to visit Windsor for a holiday rental is during the summer months, particularly from July to September. This peak season attracts families and outdoor enthusiasts eager to enjoy the vibrant community events and the beautiful landscapes that Vermont has to offer. With warm temperatures typically ranging from 20 to 27 degrees Celsius, visitors can relish in a variety of activities, from hiking and cycling to exploring the charming local shops and cafes.

July stands out as the prime month to experience Windsor's lively atmosphere, where travellers can partake in summer festivals, farmers' markets, and outdoor concerts, all set against the stunning backdrop of lush green hills. It's a delightful time for those who appreciate a bustling community vibe and the opportunity to engage with fellow adventurers.

For those looking to save a bit on their holiday, consider visiting in December. This month, while cooler with temperatures hovering around the low single digits Celsius, offers a unique charm with the festive holiday spirit and potential winter sports activities, such as skiing or snowshoeing in nearby areas. The tranquility of Windsor during this low season allows for a more intimate experience of the town and its surroundings.
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.
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 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 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.

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