
Holiday houses in Windsor
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Windsor

Total holiday rentals
Explore 80 holiday rentals in Windsor

Nightly prices starting at
Windsor holiday rentals start at $52 NZD per night before taxes and fees

Verified guest reviews
Over 2,040 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
80 of Windsor holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Windsor rentals

4.7 Average rating
Windsor stays receive an average rating of 4.7 out of 5 from guests
Top-rated holiday rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness and more.

Spacious 3 Bedroom Ranch With Office
Forget your worries in this spacious and serene space with room for 8. The entire first floor is yours to enjoy and there aren’t any shared spaces. Relax in the backyard or on the porch. 2 full bathrooms are yours to relax and enjoy. There’s a freshly remodeled bathroom in the master bedroom with walk in shower and a bathtub in the 2nd bathroom. Fully stocked kitchen awaits your inspiration. Much shopping awaits you and all the store are within 10 minutes away from you. BDL is 20 minutes away,

Apt near Big E, Six Flags, Bradley airport
Welcome to our charming and stylish upstairs apartment, perfect for a cozy retreat! Enjoy the privacy of having the entire space to yourself. Access the apartment directly through the back entrance, up the outdoor staircase. We're conveniently located just a 10-minute drive from Bradley International Airport. Inside, you'll find: - A comfortable bedroom with a Queen-sized bed, complete with fresh linens - A fully stocked kitchen, equipped: Pots, pans, baking dishes, etc Washer and dryer

Modern Cozy Studio
Experience the perfect stay in this cozy studio, nestled in the heart of Broad Brook. You'll be conveniently close to local restaurants, the Opera House, and just a short drive from Bradley International Airport, Hartford, CT, and Springfield, MA. Plus, we're pet-friendly! Enjoy direct access to Mill Pond and easy ground-level entry. There are no additional cleaning costs. Your comfort is our priority! As an added bonus, a portion of your stay supports St. Jude Children’s Research Hospital!

Premium Private Suite • Entry • Wrkspace • Parking
Welcome 🙏 to our premium private guest suite, designed for comfort, privacy, and a seamless stay. Enjoy a spacious, hotel-style retreat with a separate private entrance, easy self check-in, fast Wi-Fi, dedicated workspace, and free parking—ideal for couples, business travelers, and extended stays. Quiet, beautifully maintained, and thoughtfully designed for an stress-free experience 😊. **NO SMOKING of any kind (including cigarettes, vaping, e-cigarettes, marijuana, or any substances).

In-law apartment in Farmington River Cottage
If you are craving a getaway with a special someone, this space is meticulously clean and an opportunity to practice social distancing while relaxing and enjoying the Farmington River. Only 15 minutes from Bradley airport, 5 minutes from the train and I91. Nature, dining, all within a comfortable drive. You get it all here! Private space with its own entrance, one bedroom and newly updated bathroom, a cozy living room with fireplace in a Garden Level Unit. Off street parking available.

Island Vibes
Come and enjoy a tranquil stay with an island vibe. This 3 bedroom, 2 bath home will comfortably accommodate up to 8 persons. Large kitchen and living space for everyone. Situated in a quiet suburb on the outskirts of downtown Hartford, it is 12 minutes from Bradley International Airport, 20 minutes from the Basketball Hall of Fame and Springfield Museums Quadrangle. In the region is the Connecticut Science Museum, The Mark Twain House, Wadsworth Atheneum Museum of Art, and much more.

Your New England Summer Getaway!
Welcome to your private retreat! This unique open concept garage-converted in-law apartment offers the perfect blend of comfort and convenience. With a private entrance, a full kitchen, and space for up to 4 guests, it’s designed for both short getaways and longer stays. Whether you’re traveling for work or leisure, you’ll love the bright open feel, modern amenities, and outdoor access in a quiet neighborhood. Public park accessible and just minutes from Hartford and Bradley Airport.

Charming Cape Home, Close to All
Charming Cape Home in the Heart of Connecticut Enjoy comfort and convenience just 20 mins from Bradley Airport, 10 mins from Hartford, 25 mins from UConn, and 40 mins from New Haven. Nestled on a quiet residential street, our cozy home features multiple beds, fast Wi-Fi, Smart TVs, central air, and a fenced backyard with patio and fire pit. Grocery stores, restaurants, and coffee shops are just 5 minutes away. A perfect retreat for families, professionals, or campus visits!

Quiet Comfy Getaway 3 BDR home
Our newly renovated 3-bedroom home offers a comfortable and convenient stay. Perfectly located with easy access to the grocery stores, strip malls, hospitals, and parks, it's an ideal base for your trip. Our home comes with ample parking, pristine kitchen and bathrooms, mini coffee bar, cooking utensils, free WiFi, and a washer/dryer. Stay productive with our dedicated workspace and unwind in our spacious bedrooms. Book now for a home away from home experience!

Relax By The Water
Take it easy at this unique and tranquil getaway. Just 20 minutes from downtown Hartford, 5 minutes from Bradley airport, and conveniently close to the Loomis Chaffee school, you’ll have our entire two bedroom, two bath riverfront home to enjoy. Take in the views from the expansive balcony, enjoy a meal in the waterside dining room, or work from home in the dedicated office space. Two queen beds and a sleeper sofa sleep six comfortably. Don’t miss it!

Hilda’s Riverside Retreat
Amazing Newly renovated Airbnb! Nestled along the meandering, Connecticut River, beautiful veiw! “Just what the doctor ordered”. And just a stone’s throw away from Downtown Springfield, MGM and Hartford. Whether you are visiting the Knowledge Corridor to visit any of the 30+ universities and liberal arts colleges, business or pleasure, This waterfront property is cozy and offers every amenity you left at home!

Windy Top Cottage ~ A Romantic "European" Getaway
The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!
Popular amenities for Windsor holiday rentals
Stay near Windsor's top sights
Other great holiday rentals in Windsor

Handcrafted Timber Frame Cabin Retreat

Beautifully Renovated Riverfront Apartment Home

Bloomfield Bungalow

Grampa Potatoes Homestead LLC

Backyard Tiny House in the Woods

Newly Renovated 2 Bedroom in Heart of Tariffville

Mod-Chic 1 Bedroom with Free Parking & Wifi

By The River
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $224 NZD | $234 NZD | $224 NZD | $232 NZD | $194 NZD | $181 NZD | $188 NZD | $206 NZD | $218 NZD | $225 NZD | $227 NZD | $227 NZD |
| Avg. temp | -3°C | -1°C | 3°C | 10°C | 16°C | 20°C | 24°C | 23°C | 18°C | 12°C | 6°C | 0°C |
Frequently Asked Questions
What are the best places to stay in Windsor?
Windsor’s downtown neighborhoods and areas near parks are popular for a blend of convenience and quieter surroundings. Many guests choose residential streets with tree-lined views and easy walking access to local dining or historical sites.
What are the best things to do in Windsor with kids?
Children often enjoy the farm animals and nature center at Northwest Park, hands-on exhibits at the Windsor Historical Society, and open play areas in community parks. Seasonal family festivals and craft events add to the options.
What are some of the best things to do in Windsor?
Explore Northwest Park for walking trails and wildlife habitats, visit the Windsor Historical Society for stories of the town’s past, and browse local shops in Windsor Center. Community events and outdoor recreation round out popular activities.
How is the weather in Windsor?
Windsor has cold winters around 19–35°F (-7–2°C) and warm summers reaching 64–85°F (18–30°C). Spring and autumn bring milder temperatures and increased rainfall, so a mix of clothing layers and rain gear is practical year-round.
When is the best time to visit Windsor?
Late spring through early autumn is often recommended for milder temperatures, outdoor festivals, and lush park scenery. Fall foliage is a regional highlight, while winter stays invite cozy activities and historic museum visits.
What are the best places to visit in Windsor?
Explore the Windsor Historical Society for local history exhibits, stroll through Northwest Park’s natural spaces, or visit the historic Windsor Center for unique shops and dining. Outdoor areas and museums are frequently suggested by visitors.
What are some hiking trails in Windsor?
Northwest Park has well-maintained walking and hiking trails through forests, meadows, and wetlands, suitable for a variety of abilities. Some parks in the area include interpretive signage about local wildlife and plant life.
What are some family activities we can do in Windsor?
Families frequently explore interactive exhibits at the Windsor Historical Society, picnic or hike at Northwest Park, and attend storytimes or workshops at local libraries. Outdoor playgrounds and farm visits add to the experience for children.
What are some of the best day trip ideas from Windsor?
Many visitors explore nearby river towns for art galleries, historic sites, and scenic parks, or head toward Hartford for museums and cultural performances. Nature trails and state parks around the area draw those interested in hiking or wildlife observation.
Are there any pet friendly accommodations available in Windsor?
Windsor has a variety of pet friendly accommodations, especially in residential neighborhoods and near local parks. Many hosts welcome guests traveling with animals, so it is helpful to check listing details or message hosts about your pet’s needs.
What are some local tips for visiting Windsor?
Consider stopping by local farmers’ markets for fresh produce, or checking community calendars for seasonal events. Early mornings in the parks can be particularly peaceful, and historic districts often feature walking tour routes.
What is Windsor known for?
Windsor is known for its heritage as one of Connecticut’s oldest towns, with preserved historic sites and scenic riverfront landscapes. The community often highlights its colonial era history and thriving parks.
What are the best hidden gems to explore in Windsor?
Discover the Connecticut Valley Tobacco Museum for insight into local agricultural traditions, or explore quiet trails and birdwatching at Northwest Park. Local shops and cafes in historic Windsor Center can also provide a unique experience.
What are the best foods to try in Windsor?
Local menus feature classic New England dishes such as clam chowder, baked goods made with regional fruit, and comfort foods found in neighborhood diners. During the harvest season, you can frequently sample corn, apples, and maple products from area farms.
What should I bring for a trip to Windsor?
Pack clothing layers for temperature changes, a waterproof jacket for unexpected rain, and comfortable shoes for exploring parks or walking through historic districts. In summer, sunscreen and insect repellent are helpful for outdoor activities.
What is the nightlife in Windsor like?
Windsor’s nightlife is relaxed, with locally owned restaurants, taverns, and occasional live music around town. Social events and gatherings often center near Windsor Center and community venues.
What are the most popular events or festivals in Windsor?
Windsor is known for community gatherings that often highlight local culture, history, and seasonal traditions. Annual events frequently suggested include outdoor summer concerts, agricultural fairs, and multicultural celebrations.
Are there family friendly vacation rentals in Windsor?
Windsor has a range of family friendly vacation rentals, with options near parks, schools, and residential neighborhoods. Many homes include features like multiple bedrooms, kitchens, and access to outdoor spaces.
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