
Holiday rentals in Windsor
Find and book unique accommodation on Airbnb
Top-rated holiday 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,

Paradise On The Hill Luxury Apartment.
Enjoy your own special and separated section of this beautiful, modern colonial home. This spacious home includes central air, an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large, newly renovated bathroom with spa like jets. His and hers closets. Beautiful fully stocked kitchenette, 2 large screen Smart TVs, 55 inch in living room, 42 inch in bedroom, Free WiFi, dining for 6, all for the comfort and convenience of our guests.

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

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!

Best River View, on Rail Trail in Collinsville!
This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

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!

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!

Waterfront Bliss Tiny Home
Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!
Popular amenities for Windsor holiday rentals
Stay near Windsor's top sights
Other great holiday rentals in Windsor

West Hartford Center Apartment 2

Mod-Chic 1 Bedroom with Free Parking & Wifi

Crested One Place - Heat & Free Parking included

By The River

The Hangar

Spacious 2BR | Long Stays + WiFi + Parking

Eden’s Cozy Nest

Home Away from Home
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £97 | £102 | £97 | £101 | £85 | £79 | £82 | £90 | £95 | £98 | £99 | £99 |
| 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.
Where should I stay in Windsor?
Make yourself at home in Windsor by choosing from our most frequently booked neighborhoods. We have over 30 vacation rentals in Hayden, and over 80 vacation rentals in Windsor Locks.
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.
What are the most popular amenities for House Rentals in Windsor?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wifi, over 30 homes with a kitchen, over 40 homes with free parking, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Windsor

Total holiday rentals
Explore 70 holiday rentals in Windsor

Nightly prices starting at
Windsor holiday rentals start at £22 per night before taxes and fees

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

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
70 of Windsor holiday rentals include wifi 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
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Yale University
- Six Flags New England
- Mohegan Sun
- Ocean Beach Park
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Foxwoods Resort Casino
- Mystic Seaport Museum
- Bash Bish Falls State Park
- Mohawk Mountain Ski Area
- Taconic State Park
- Hammonasset Beach State Park
- Kent Falls State Park
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Yale University Art Gallery
- Ski Sundown
- Mount Southington Ski Area
- University of Connecticut
- Naumkeag
- Ocean Beach
- Mystic Aquarium
- Norman Rockwell Museum
- Soundview Beach





