Windsor holiday lettings

We found 249 holiday rentals — enter your dates for availability

Discover a selection of 6 homes and other holiday rentals in Windsor that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, including Wi-Fi and parking. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

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Head to the friendly city of Windsor

Learn about the unique charm of Windsor with a stay in a holiday home rental. This welcoming and romantic city is well known for its restaurants, shopping and theme park. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Windsor

Do you want to discover attractions to see while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Windsor has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Gillette Ridge Golf Course (5.9 mi / 9.5 km)
  • Wintonbury Hills Golf Course (5.9 mi / 9.6 km)
  • Cabela's (6.8 mi / 10.9 km)
  • Talcott Mountain State Park (7.8 mi / 12.5 km)
  • Flamig Farm (11.4 mi / 18.4 km)
  • Sonny's Place (12.9 mi / 20.8 km)

Exploring the natural features in Windsor

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

  • Northwest Park (4.2 mi / 6.8 km)
  • Windsor Nature Park (4.6 mi / 7.3 km)
  • South Windsor Bark Park (5.1 mi / 8.2 km)
  • Riverside Park (5.3 mi / 8.6 km)
  • Wickham Park (5.8 mi / 9.3 km)
  • Connecticut River (6.1 mi / 9.8 km)

Transport options to and around Windsor

The nearest airport is in Hartford, CT (BDL-Bradley Intl.), located 5.8 mi (9.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Westfield, MA (BAF-Barnes Municipal), which is 22.1 mi (35.6 km) away.

If you're travelling 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 planning a holiday rental in Windsor, Connecticut, one of the best areas to consider is the vibrant neighbourhood of Windsor Locks. This charming area is conveniently located near Bradley International Airport, making it ideal for travellers who appreciate accessibility. Windsor Locks boasts a variety of rental properties, ranging from quaint homes to spacious apartments, providing a comfortable stay for families and solo travellers alike.

A key attraction in Windsor Locks is the New England Air Museum, which showcases an impressive collection of aircraft and aviation exhibits, superb for aviation enthusiasts and families looking for an educational outing. Additionally, the scenic Farmington River flows nearby, offering opportunities for leisurely walks, picnics, and even kayaking during the warmer months.

Another excellent area to explore is the historic downtown Windsor. This area features a delightful mix of shops and cafes, where visitors can experience the local culture and cuisine. The Windsor Historical Society is a great point of interest, offering insights into the town's rich history and heritage. With a range of properties available here, you can easily find a charming spot to relax after a day of exploration.
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.
What is the most popular type of holiday rental accomodation in Windsor?
In Windsor, holiday houses and cottages are popular rental options, with several available throughout the area. These accommodations typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many properties also offer outdoor spaces, such as gardens or patios, where guests can relax and enjoy the pleasant surroundings.
Are there any family house rentals in Windsor?
In Windsor, Connecticut, there are several family-friendly house rentals available, making it a great spot for those travelling with children. The area offers spacious homes, often featuring multiple bedrooms and ample living space to accommodate families comfortably. Many of these properties come equipped with full kitchens, allowing for easy meal preparation, as well as outdoor spaces for kids to play.
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, Connecticut, there are several pet-friendly house rentals available, making it a welcoming destination for travellers with furry companions. Many of these properties are equipped with amenities such as spacious backyards, fully furnished kitchens, and comfortable living areas, great for families or groups. Some rentals may also feature outdoor spaces ideal for pets to roam and play.
Are there any remote work holiday rentals in Windsor?
In Windsor, Connecticut, there are several remote work holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties come equipped with amenities tailored for remote work, such as dedicated desk spaces, comfortable chairs, and reliable Wi-Fi, allowing for a productive environment. Some accommodations also feature additional conveniences like laptop workspaces and computer monitors, suiting the needs of business travellers. 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 typically include kitchens equipped with essential cookware, dishware, utensils, dishwashers, microwaves, and refrigerators. These features allow travellers to prepare their own meals and enjoy a more homely experience during their stay. Many rentals are situated in neighbourhoods that offer easy access to local attractions, parks, and the scenic Connecticut River, making them convenient for both relaxation and exploration.
When is the best time to visit Windsor for a holiday rental?
July marks the peak time to visit Windsor, Connecticut, making it an ideal month for those seeking a vibrant holiday experience. During this period, the weather is warm, typically ranging in the low 30s Celsius, providing superb conditions for outdoor activities and sightseeing. The town comes alive with numerous events, including festivals and concerts, inviting visitors to immerse themselves in the local culture.

From July through September, the area buzzes with activity, as families and adventure seekers flock to enjoy the scenic parks, historic sites, and the beautiful Connecticut River. This lively atmosphere creates a wonderful opportunity for socializings and shared experiences among fellow travellers.

For those looking to save on accommodation costs, consider visiting in December. While this month falls within the low season, it offers a unique charm with festive decorations and community events that capture the holiday spirit. You can enjoy a quieter pace, allowing for leisurely strolls through Windsor's picturesque streets and perhaps a visit to local shops for holiday gifts.
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 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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