Windsor holiday homes

We found 239 holiday rentals — enter your dates for availability
Discover a selection of 9 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.

Holiday rentals with weekly discounts – Windsor

Showing deals for:18 Dec - 25 Dec

walking distance private beach at lake
walking distance private beach at lake
Living area
Exterior
Exceptional
(8 reviews)

Lake Congamond Cozy Stylish Comfortable House

Suffield

7% off
NZ$3,831
for 7 nights, 1 home
NZ$547 per night
includes taxes & fees
Lake Congamond Cozy Stylish Comfortable House
Terrace/patio
Dining
Private kitchen
Interior
Exceptional
(5 reviews)

Modern Family Retreat w/ Office & Fast WiFi

East Hartford

7% off
NZ$7,428
for 7 nights, 1 home
NZ$1,061 per night
includes taxes & fees
Modern Family Retreat w/ Office & Fast WiFi
Independent entrance
Private kitchen
Outdoor dining
Property grounds
Exceptional
(78 reviews)

Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

Suffield

8% off
NZ$3,246
for 7 nights, 1 apartment
NZ$464 per night
includes taxes & fees
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
Interior
Private kitchen
Dining
Living area
Exceptional
(11 reviews)

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Windsor Locks

16% off
NZ$4,239
for 7 nights, 1 home
NZ$606 per night
includes taxes & fees
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Room
Terrace/patio
Living area
Interior
Exceptional
(10 reviews)

WeHa Penthouse w/ Private Deck

West Hartford

8% off
NZ$2,157
for 7 nights, 1 home
NZ$308 per night
includes taxes & fees
WeHa Penthouse w/ Private Deck
Private kitchen
Living area
Room
Interior
Wonderful
(28 reviews)

New!Quaint & Convenient Hideaway: Great Location

East Hartford

7% off
NZ$2,493
for 7 nights, 1 home
NZ$356 per night
includes taxes & fees
New!Quaint & Convenient Hideaway: Great Location

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    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • East Hartford Golf Course (5 mi / 8 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)
  • Riverside Park (5.3 mi / 8.6 km)
  • Wickham Park (5.8 mi / 9.3 km)
  • Connecticut River (6.1 mi / 9.8 km)
  • Mortensen Riverfront Plaza (6.2 mi / 9.9 km)
  • Bushnell Park (6.3 mi / 10.2 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 Springfield Union Station (ZSF), which is 17.7 mi (28.5 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 considering a holiday rental in Windsor, Connecticut, the area around the historic town centre is highly recommended. This neighbourhood offers a charming blend of quaint New England architecture and modern conveniences, providing a delightful atmosphere for visitors. One of the top attractions nearby is the Windsor Historical Society, which showcases the town's rich heritage through engaging exhibits. Additionally, the stunning Windsor Locks Canal State Park offers lovely walking trails and picturesque views, great for those who enjoy the outdoors.In terms of holiday rentals, the town centre features a variety of properties ranging from cosy apartments to spacious homes, suiting different group sizes and preferences. Staying in this area allows easy access to local shops, restaurants, and parks, making it an ideal base for exploring Windsor and its surroundings.
What is the most popular type of holiday rental accomodation in Windsor?
In Windsor, apartments are the most popular holiday rental option, with around 21 available in various neighbourhoods close to the Connecticut River and the vibrant downtown area. These apartments typically feature fully equipped kitchens, spacious living areas, and often include modern amenities such as Wi-Fi and laundry facilities, making them ideal for both short and extended stays.In addition to apartments, there are approximately 18 holiday houses, which provide more space and privacy, great for families or groups. These houses generally come with multiple bedrooms, outdoor spaces for relaxing, and sometimes even BBQ facilities for enjoyable gatherings. There are also several charming cottages available, offering a quaint and homely atmosphere, often set in more tranquil surroundings.
Are there any family house rentals in Windsor?
In Windsor, Connecticut, there are several family-friendly house rentals available, making it a suitable destination for those travelling with children. The area features a mix of neighbourhoods where visitors can find spacious properties close to local parks and family-friendly attractions. Many of these homes come equipped with amenities such as full kitchens, outdoor spaces for barbecues or play, and comfortable living areas for relaxation after a day of exploring.Nearby, families can enjoy lovely outdoor activities in parks like Windsor's Northwest Park, which offers walking trails, nature exhibits, and playgrounds. Additionally, the historical charm of Windsor is evident in its old-town areas, where families can experience local culture and history.
Can I rent a holiday home with a pool or hot tub in Windsor?
In Windsor, Connecticut, there are several holiday homes available for rent that feature pools and hot tubs. This charming town, located near the Connecticut River, offers a peaceful environment for travellers seeking relaxation. Many of the rentals come equipped with private pools and hot tubs, providing a great retreat for families or groups. Expect amenities such as spacious outdoor areas, fully equipped kitchens for cooking, and comfortable living spaces for unwinding after a day of exploring.
Are there pet-friendly house rentals in Windsor?
In Windsor, Connecticut, there are several pet-friendly house rentals available for those travelling with furry companions. Many of these properties offer a range of amenities, including spacious backyards, fully equipped kitchens, and comfortable living areas, making them suitable for families or groups.The area is conveniently located near parks and green spaces, providing ample opportunities for outdoor activities with pets. Notable spots include Windsor Town Green and the nearby Northwest Park, where you can enjoy walking trails and picnic areas. These parks are superb for leisurely strolls or energetic playtime with your pets, enhancing the overall experience of your stay in Windsor.
Are there any remote work holiday rentals in Windsor?
In Windsor, Connecticut, there are approximately 33 holiday rentals that cater to remote work needs. This charming town, rich in history and situated along the Connecticut River, offers a variety of properties ideal for those seeking a conducive work environment. Many rentals come equipped with amenities such as free Wi-Fi in both public areas and individual rooms, ensuring seamless connectivity for remote workers. Additionally, you'll find desks and desk chairs in the accommodations, providing a comfortable workspace.Beyond the practical amenities, Windsor boasts a picturesque setting with easy access to parks and local attractions, making it an enjoyable place to unwind after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Windsor?
In Windsor, popular holiday rental amenities include fully equipped kitchens, allowing travellers to prepare their own meals during their stay. Many properties also feature dedicated workspaces, making them suitable for business travellers or those needing to catch up on work. Onsite parking is commonly available, providing convenience for guests with vehicles. Additionally, dining areas are a standard feature, offering comfortable spaces for meals. Air conditioning is also prevalent, ensuring a pleasant environment during warmer months.
When is the best time to visit Windsor for a holiday rental?
The best time to visit Windsor for a holiday rental is during the summer months, particularly in July, when the town comes alive with vibrant activities and warm weather. Peak tourist season spans from July to September, attracting families and outdoor enthusiasts eager to explore the scenic beauty and local attractions.In July, visitors can enjoy pleasant temperatures averaging around 25 to 30 degrees Celsius, great for outdoor activities such as hiking in nearby parks or enjoying picnics along the Connecticut River. The lively option fosters a sense of community, with various events and festivals taking place, making it an ideal time for families and groups looking to create memorable experiences together.For those seeking a more budget-friendly option, consider visiting in December. This month offers a unique charm with festive decorations and holiday events, providing a quieter atmosphere for exploration. While the temperatures may dip to around 0 to 5 degrees Celsius, the cozy appeal of holiday decorations and local festivities can make it a delightful time to experience Windsor.
What are the top attractions in Windsor?
In Windsor, Connecticut, visitors can explore a range of attractions that highlight the town's rich history and natural beauty. The Windsor Historical Society offers an insightful look into the area's past, showcasing local artefacts and exhibits. Just a short distance away, the picturesque Connecticut River provides opportunities for scenic walks and outdoor activities, with parks like the Windsor Riverwalk and Discovery Park offering lovely views and picnic spots.For those interested in nature, the nearby Northwest Park features walking trails, a nature centre, and a lovely pond, making it a great spot for hiking and birdwatching. If you're looking for cultural experiences, the Hartford area is also easily accessible, where the Wadsworth Atheneum Museum of Art and the Mark Twain House & Museum can be found.
Are all fees included in the Windsor holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Windsor holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Windsor holiday homes?
You can find great discounts on holiday homes in Windsor on Bookabach, 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 change or cancel my Windsor holiday home booking on Bookabach?
To find Windsor holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Windsor?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Windsor holiday home?
Book your Windsor holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Windsor?
Prices for holiday homes 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. Bookabach offers something for every taste and budget, from affordable homes in Windsor to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.