
Family-friendly holiday rentals in Windsor
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Windsor

Total holiday rentals
Explore 20 holiday rentals in Windsor

Nightly prices starting at
Windsor holiday rentals start at $102 NZD per night before taxes and fees

Verified guest reviews
Over 850 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 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 family-friendly rentals in Windsor
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Hidden Cozy Waterfront Eco Cabin Nature Sanctuary
Welcome to Otter Falls Inn! Nestled in the trees directly above the brook and hidden off the main road sits our cozy, vintage eco cottage. Just 8 minutes from all major conveniences, our property is a hidden oasis- an urban nature sanctuary where we are restoring native habitat and the waterway. We lovingly restored and updated the cottage to offer a unique, relaxing, romantic getaway where guests can slow down and enjoy connecting to each other and nature in this stylish, eco conscious home.
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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,
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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
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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!
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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).
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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.
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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.
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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!
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Spacious 3BR Home | Sleeps 8 | Near Hartford & BDL
Welcome to our newly renovated 3-bedroom home in Windsor, CT! Sleeps up to 8 guests and is perfect for families, business travelers, healthcare professionals, and extended stays. Enjoy fast WiFi, a dedicated workspace, fully equipped kitchen, complimentary coffee bar, washer/dryer, free parking, and spacious bedrooms. Minutes from Hartford, Bradley Airport (BDL), hospitals, shopping, dining, and major highways.
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Home away from home
Enjoy this stylish third-floor apartment with two cozy bedrooms, each featuring a queen bed. The space includes a fully equipped kitchen, modern full bathroom, and a private balcony—perfect for relaxing. Just steps from Joey’s Pizza Pie and Park Lane Pizza, you’ll be in the heart of West Hartford’s best dining. Ideal for work trips or getaways, this apartment offers comfort, convenience, and charm.
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FROG Suite Apartment
Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.
Indoor spacesFamilyWalkability
Flamig Farm Staycation
Very charming private farmhouse tastefully decorated situated in rural West Simsbury CT. Learn every day farm life from helping gather the 200 eggs daily and morning chores of caring for and feeding the petting zoo animals. Please note you are welcome to help the farmer as a family, but please do not leave children unsupervised.
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Popular amenities for Windsor family-friendly rentals
Family-friendly home rentals with a hot tub

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away
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Luxe Bolton Lake
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HOT TUB! Dog & Family Friendly in the Berkshires!
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Breathtaking home with unforgettable views & pool!
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Cozy cottage 5 minutes from UConn
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4 BR Entire House w/Hot Tub
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Lake Views from Hot Tub Propane Fire Pit 4 Kayaks
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Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes
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Family- and pet-friendly home rentals

10 Hillcrest
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The Little Red Schoolhouse ~ Circa 1877
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Peaceful Pet-Friendly Retreat Near Hartford and MA
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Bedroom Forest View I Sauna I Fire-pit I Trails
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Guesthouse Farm Stay
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Bright & Private WHOLE HOUSE 4 YOU Near Everything
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Trainmaster's Inn - Caboose
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Water Forest Retreat -Octagon
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Family-friendly home rentals with a pool

Farm Stay with Horses & Pool | Mountaintop Views
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The Creation Station
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The Getaway-HOST & Co.
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Luxe 1822 Apt | Rain Shower | Plush beds | Firepit
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1880s skylit design apt w balcony, best location
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Top Rated Villa located near Mohegan Sun & Mystic
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NE Historical Mansion-pets and pet lovers welcome
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Romantic Spa Retreat minutes to Mohegan Sun Casino
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When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $304 NZD | $304 NZD | $316 NZD | $327 NZD | $327 NZD | $301 NZD | $304 NZD | $293 NZD | $281 NZD | $296 NZD | $315 NZD | $301 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 |
Destinations to explore
- New York City Holiday rentals
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- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Six Flags New England
- Ocean Beach Park
- Mystic Aquarium
- Mystic Seaport Museum
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Taconic State Park
- University of Connecticut
- Bash Bish Falls State Park
- Kent Falls State Park
- Soundview Beach
- Hammonasset Beach State Park
- Mohawk Mountain Ski Area
- Powder Ridge Mountain Park & Resort
- Ocean Beach
- Sleeping Giant State Park
- Yale University Art Gallery
- Ski Sundown
- Wesleyan University
- University of Massachusetts Amherst
- Naumkeag





