Windsor holiday lettings

We found 92 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Windsor that are perfect for your trip. Holiday rentals provide the best amenities for your stay with friends, family or just your pet, such as air conditioning and cable TV. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind

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  • More quality time

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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

Find the perfect holiday rental for your Windsor getaway

Learn about the unique charm of Windsor with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Windsor

Do you want to find top things to see and do while you're in town? Venture out of your cosy holiday rental and experience everything that makes Windsor a fun spot to go on holiday. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Eaton's Magic Morsel (6.9 mi / 11.1 km)
  • Quilted Threads (10.5 mi / 16.9 km)
  • Crotched Mountain Golf Club (11.6 mi / 18.7 km)
  • Pats Peak (11.7 mi / 18.9 km)
  • Crotched Mountain Ski and Ride Area (11.9 mi / 19.2 km)
  • Granite Gorge (15.3 mi / 24.6 km)

Exploring the natural landscape of Windsor

Whether you're looking for adventure or just want to take in the scenery, Windsor is a great place to get out in nature. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Highland Lake (5.2 mi / 8.4 km)
  • Granite Lake (10.2 mi / 16.4 km)
  • Contoocook River (10.6 mi / 17 km)
  • Nubanusit Lake (11 mi / 17.6 km)
  • Blaisdell Lake (11 mi / 17.8 km)
  • Horace Lake (12.5 mi / 20.1 km)

Transport options to and around Windsor

Fly into Concord, NH (CON-Concord Municipal), the closest airport, located 26.4 mi (42.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Springfield, VT (VSF-Hartness State), which is 28.6 mi (46 km) away.

Frequently asked questions

What is the best area to stay in Windsor when booking a holiday rental?
When considering a holiday rental in Windsor, New Hampshire, the area around the charming village centre is an excellent choice. This picturesque neighbourhood offers a blend of quaint New England charm and convenient access to local attractions. Visitors will find a variety of properties to suit different tastes and budgets, making it a popular spot for those looking to immerse themselves in the local culture.

One of the highlights nearby is the stunning Mount Sunapee State Park, which provides ample opportunities for outdoor activities, including hiking and skiing, depending on the season. Additionally, the local art scene is vibrant, with galleries and studios showcasing the work of talented local artists, adding to the area's appeal.

Staying in this part of Windsor also puts you in close proximity to the serene beauty of Lake Sunapee, superb for leisurely days by the water or engaging in water sports.
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.
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 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.
When is the best time to visit Windsor for a holiday rental?
July is the most popular month to visit Windsor, New Hampshire, drawing in travellers eager to enjoy the natural beauty and outdoor activities this charming destination has to offer. The peak season stretches from May to July, when visitors flock to the area for hiking, boating, and exploring the picturesque landscapes that the region is known for. With temperatures often reaching the low 20s Celsius, the warm summer weather creates a superb environment for outdoor adventures and leisurely strolls around the town.

During this peak season, you'll find an energetic atmosphere, with plenty of opportunities to engage in local festivities and community events. July, in particular, is vibrant, with families and friends gathering to celebrate summer in the stunning surroundings of Windsor.

For those looking for a more budget-friendly option, consider planning your visit in October. This month showcases the stunning autumn foliage, providing a beautiful backdrop for scenic drives and nature walks. The cooler temperatures, averaging around 10 to 15 degrees Celsius, make it comfortable for outdoor explorations while enjoying the quieter atmosphere that October brings.
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, New Hampshire, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. The nearby Lake Sunapee is a popular spot for swimming, boating, and fishing during the warmer months, while the surrounding mountains offer excellent hiking trails with stunning views.

The town itself is known for its charming rural atmosphere, with opportunities for scenic drives through the picturesque landscape. Additionally, the area is close to the White Mountain National Forest, which provides ample opportunities for outdoor adventures such as hiking, camping, and wildlife watching.

For those interested in local history, the nearby town of New London features the New London Historical Society and the charming main street with quaint shops and cafes.
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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