
Vacation rentals in Windsor
Find and book unique accommodations on Airbnb
Quick stats about vacation rentals in Windsor

Total vacation rentals
Explore 70 vacation rentals in Windsor

Nightly prices starting at
Windsor vacation rentals start at R 495 ZAR per night before taxes and fees

Verified guest reviews
Over 1,840 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
70 of Windsor vacation rentals include wi-fi access

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

4.6 Average rating
Windsor stays receive an average rating of 4.6 out of 5 from guests
Top-rated vacation rentals in Windsor
Guests agree: these stays 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.

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,

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!

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

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.

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.

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!

Peaceful Pet-Friendly Retreat Near Hartford and MA
Welcome to your home away from home located steps away from downtown Manchester CT! ✔ Private entrance ✔ 1 comfortable bedroom & full bathroom ✔ Fast Wi-Fi for work and entertainment ✔ In-unit washer & dryer ✔ Complimentary coffee ✔ Pet-friendly accommodations ✔ Backyard access ✔ Quiet, residential setting Conveniently located close enough to major events but in a quaint downtown area making it prefect for short or long term stays.

Loft - Queen Anne Row House in a historic district
Hosted by Judy and Greg, our home is close to art, culture, live theater, and restaurants. Our home is also close to major insurance companies, the state capitol and state of Connecticut offices and several universities. You’ll love the cozy 3rd floor loft. We also offer off street parking. Garage space is also available as an option. Our home is a perfect destination for couples, solo adventurers, and business travelers.

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!

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.

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 a stress-free experience 😊.
Popular amenities for Windsor vacation rentals
Stay near Windsor's top sights
Other great vacation rentals in Windsor

The Hangar

By The River

The Majestic View | Luxury Stay Golf Views

Relax By The Water

Spring in the Heart of New England!

Bloomfield Bungalow

Rustic Farmhouse by the River (Duplex)

Backyard Tiny House in the Woods
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 2,146 ZAR | R 2,245 ZAR | R 2,146 ZAR | R 2,228 ZAR | R 1,865 ZAR | R 1,733 ZAR | R 1,799 ZAR | R 1,981 ZAR | R 2,096 ZAR | R 2,162 ZAR | R 2,179 ZAR | R 2,179 ZAR |
| 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
Are there family-friendly vacation rentals in Windsor?
Windsor has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Windsor?
Experience the best of Windsor with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Windsor?
Four-legged friends are welcome in Windsor. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Windsor?
Yes! Work meets play with ease at over 50 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Windsor have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windsor have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windsor have wifi?
Absolutely! We offer over 40 house rentals with wifi in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windsor have free parking?
Absolutely! We offer over 40 house rentals with free parking in Windsor. Enjoy a tailored experience with all the comforts you desire.
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