Windsor holiday rentals

We found 242 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

Terrace/patio
Dining
Interior
Private kitchen
Exceptional
(5 reviews)

Modern Family Retreat w/ Office & Fast WiFi

East Hartford

7% off
AU$5,987
for 7 nights, 1 home
AU$855 per night
includes taxes & fees
Modern Family Retreat w/ Office & Fast WiFi
Private kitchen
walking distance private beach at lake
Living area
walking distance private beach at lake
Exceptional
(8 reviews)

Lake Congamond Cozy Stylish Comfortable House

Suffield

7% off
AU$3,115
for 7 nights, 1 home
AU$445 per night
includes taxes & fees
Lake Congamond Cozy Stylish Comfortable House
Outdoor dining
Private kitchen
Games room
Independent entrance
Exceptional
(78 reviews)

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

Suffield

8% off
AU$2,657
for 7 nights, 1 apartment
AU$380 per night
includes taxes & fees
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
Interior
Private kitchen
Room
Dining
Exceptional
(11 reviews)

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

Windsor Locks

16% off
AU$3,447
for 7 nights, 1 home
AU$492 per night
includes taxes & fees
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Living area
Terrace/patio
Interior
Dining
Exceptional
(10 reviews)

WeHa Penthouse w/ Private Deck

West Hartford

8% off
AU$1,751
for 7 nights, 1 home
AU$250 per night
includes taxes & fees
WeHa Penthouse w/ Private Deck
Interior
Living area
Private kitchen
Room
Wonderful
(28 reviews)

New!Quaint & Convenient Hideaway: Great Location

East Hartford

7% off
AU$2,062
for 7 nights, 1 home
AU$295 per night
includes taxes & fees
New!Quaint & Convenient Hideaway: Great Location

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Why visit Windsor

  • Historic charm: Wander through the Windsor Historic District, admiring beautifully preserved homes and significant landmarks.
  • Iconic bridge: Cross the Windsor Bridge, a quintessential emblem of the town's rich heritage.
  • Urban parks: Enjoy scenic strolls and picnics in the town's well-kept green spaces.
  • Local exploration: Meander along Windsor Street and Windsor Road for a taste of local shops and eateries.
  • Family-friendly fun: Revel in diverse outdoor activities and cultural experiences that suit every traveller.

Popular types of accommodation in Windsor

Discover Windsor, Connecticut – a charming city offering a variety of holiday accommodation options including private holiday homes, cosy cottages and modern apartments. Enjoy a rooftop terrace, spacious bathroom house, family home or comfortable bedroom houses, perfect for a fantastic rental opportunity. With a rich blend of local attractions and landmarks, Windsor invites you to explore its unique experiences and welcoming community.

  • Private Holiday Homes: The top choice among visitors, offering exclusive and cosy retreats for a memorable stay in Windsor.
  • Cottages: A charming option, these quaint abodes provide a picturesque setting for a delightful holiday experience.
  • Apartments: Modern and well-appointed, these units offer comfort and convenience for a relaxing break.
  • Cabins: Ideal for those seeking a rustic escape, these cosy lodgings blend simplicity with scenic charm.
  • Condos: Stylish and contemporary, these properties provide a refined base for exploring Windsor.**

Top attractions near Windsor

Windsor, Connecticut offers a delightful mix of attractions for families, couples, and outdoor enthusiasts. Explore its urban parks, historic houses, and nature reserves, which provide an ideal backdrop for a cultural and relaxing holiday. A visit to the iconic Windsor Bridge adds to the charm, ensuring a memorable experience within this quaint American town.

  • Mark Twain House & Museum: A historic house imbued with cultural ambience, offering insight into literary history, located 11km from Windsor.
  • Elizabeth Park: An urban park with a city, family, outdoor atmosphere, perfect for leisurely strolls, located 11km from Windsor.
  • Connecticut State Capital: A historic civic government building exuding cultural charm, situated 10km from Windsor.

Things to do recommended for couples

Windsor offers a delightful escape for couples. Take a leisurely stroll along the scenic banks of the Connecticut River or enjoy a picnic at the picturesque Northwest Park. For an intimate evening, dine at a charming local restaurant, savouring exquisite cuisine together.

Things to do recommended for families

Families visiting Windsor can explore the charming Windsor Historical Society to learn about local heritage and enjoy interactive exhibits. A scenic walk along the Farmington River adds to the delightful experience for all ages.

Things to do recommended for groups

Groups visiting Windsor, Connecticut, can experience the thrill of motor racing at Stafford Motor Speedway, located 29km away. This venue offers an exciting atmosphere perfect for adventure seekers, making it an ideal spot for a memorable group outing.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Windsor

Whether you're journeying with a group, travelling as a family, accompanied by your pets, or seeking extended stays, ensure you prioritise the right filters. Here are some Stayz booking tips for you.

  • Traveling to Windsor with a group: Consider how many bedrooms will be required, along with facilities like a fully-equipped kitchen or an outdoor area for group gatherings. Fortunately, on Stayz you can filter for all of these features and more.
  • Traveling to Windsor with young kids: Traveling with young children can be challenging. You must prioritise their comfort and safety, ensuring access to age-appropriate facilities, such as a private swimming pool. It is also advisable to consider your closeness to family-friendly attractions.
  • Taking your pets with you to Windsor: For many, a family holiday simply isn’t complete without their furry companion. If that resonates with you, consider browsing Stayz properties that welcome pets. Numerous pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels right at home.
  • Planning for a long term stay visiting Windsor: If you are seeking holiday lets offering discounts for stays of a month or more, you have come to the right place. With the appropriate filter, you can effortlessly discover and save on monthly lets. You might also consider including a parking space, a well-equipped kitchen or a private pool in your search.

Where to stay near Windsor

Windsor, Connecticut, offers a delightful blend of family-friendly activities and romantic spots for every traveller. Explore the charming Windsor Historic District, featuring beautifully preserved homes and historical landmarks. Enjoy the scenic parks perfect for outdoor adventures and picnics. Stroll along Windsor Street to experience local shops and eateries, while the serene atmosphere of Windsor Road invites leisurely walks. Whether you're seeking history or outdoor fun, Windsor promises a memorable holiday experience.

  • Hartford: Hartford, a vibrant city located 11km away from Windsor, offers a diverse travel experience. Visitors can enjoy a blend of family, romantic, and city-themed adventures. The city is renowned for its rich cultural scene, featuring activities such as educational visits, theatre performances, and live music concerts. Notable nearby landmarks include an event conference venue, a convention centre, and a historic college university, providing a unique mix of heritage and modernity.
  • West Hartford: West Hartford is a lively city situated 13km from Windsor, celebrated for its city-themed, family-friendly, and outdoor attractions. The area boasts a range of engaging activities, from exploring educational and shopping areas to enjoying a round of golf at a local course. Among the highlighted attractions are a historic college university, an event conference venue, and an urban park, each adding to the region's diverse appeal and inviting ambiance.
  • South Windsor: South Windsor, only 6km away from Windsor, promises a dynamic blend of city-themed, family-oriented, and business-themed experiences. This vibrant locale offers activities such as educational tours, music concerts, and visits to resort areas. Key attractions in the vicinity include an event conference venue, a historic college university, and a convention centre, creating a well-rounded destination that caters to varied interests and tastes.

Best time to go to Windsor

If you're planning a trip to Windsor, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January27.9°F (-2.3°C)Light RainMostly SunnyAverageSlightly Low
February29.3°F (-1.5°C)Light RainMostly SunnyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly SunnyAverageSlightly Low
April48.4°F (9.1°C)Light RainMostly SunnySlightly HighAverage
May59.2°F (15.1°C)Light RainMostly SunnyAverageSlightly High
June67.3°F (19.6°C)Light RainMostly SunnyAverageAverage
July73.9°F (23.3°C)Light RainMostly SunnySlightly HighSlightly High
August72.1°F (22.3°C)Light RainMostly SunnyAverageSlightly High
September65.1°F (18.4°C)Light RainMostly SunnySlightly HighAverage
October54.0°F (12.2°C)Light RainMostly SunnySlightly LowAverage
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December34.2°F (1.2°C)Light RainMostly SunnySlightly LowAverage

Booking with Stayz is a breeze

Looking to stretch your travel budget further? Consider remaining flexible with your travel dates, as prices can vary. Additionally, booking a longer stay often results in significant savings. To find the ideal Stayz property suited to your budget, use our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board provides an organised platform for you to plan new journeys, manage your existing arrangements, or review your bookings. Your saved or reserved properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover the features of Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

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)
  • 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)
  • Six Flags New England (13 mi / 21 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 Stayz.
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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Windsor holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Windsor to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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