
Vacation rentals in Windsor
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Top-rated vacation rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness, and more.

WeHa Penthouse w/ Private Deck
Welcome to our cozy penthouse-style apartment, where comfort meets tranquility. Enjoy a private deck with exceptional views of West Hartford. Treat yourself with our minibar and indulge without leaving your unit. Centrally located, our apartment provides easy access to the best of West Hartford. Explore Blue Back Square, a vibrant dining hub just 5 minutes away. For a leisurely experience, walk 2 minutes to Park Rd and discover culinary delights like Plan B, Americano Bar, and Zaytoon’s Bistro.

Executive Stay Downtown Hartford
Enjoy a perfect upscale and stylish experience at this centrally located stay in downtown Hartford. With beautiful views of downtown Hartford overlooking our central park known as "The Green", this unit has everything you need (+blackout curtains) . This is Immediately across the street from the XL Center, home of our UCONN HUSKIES, and a short, quick walk from the executive buildings. Come enjoy an amazing stay at one of the premier locations in the city. (Also includes easy parking access.)

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

Cozy studio loft
Home away from home! In a serene, wooded area tucked away from the road, you'll find our studio loft mother-in-law apartment. Beautiful views with wildlife often spotted. Well-lit with many windows to let in the morning light. Suitable for a change of scenery while working remotely, a brief stay between locations, or your actual destination. UConn is minutes down the road. Looking for antiques? Stafford Speedway? Mohegan Sun or Foxwoods visits? Outdoor enthusiast? This place works for all!

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.

Guest Suite with Private Entrance & View
Relax at our Guest Suite Apartment with a private walk-out entrance on the lower level of our home. Nestled at the end of a quiet neighborhood road our space is just 15 minutes from Bradley Airport & less than an 8-mile drive from Hartford. Have fun with the local bike path, hiking, wineries, and breweries. Afterward, kick up your feet on the queen mattress or unwind on the patio in our peaceful backyard often visited by deer.

Paradise On The Hill Luxury Apartment.
Enjoy your own special and separated section of this beautiful, modern colonial home. This beautiful home includes an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large bathroom with spa like jets. His and hers closets. Beautiful kitchenette. 50 inch T.V., Free WiFi. , comfortable dining and more, all for the comfort and convenience of our guests.

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. 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.

Staying at Ten Hillcrest
What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

Private 1 BR Suite in West Hartford CT Home
Private 1 BR Queen Suite with large living room, full kitchen, 1.5 Baths and separate entrance. Ideal for long-term stays. Quiet residential neighborhood close to West Hartford Center and Elizabeth Park. Quick drive to U of Hartford, Trinity College, UConn Law/Medical, St. Francis and Hartford Hospitals. Two blocks to pizza, bakery, market & liquor store.

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.

Linny’s Lake Retreat-Family-Friendly & Dock Access
Linny’s Lake Retreat-Family-Friendly & Dock Access 🌲🌳 Charming Lakeside Cottage on South Pond Welcome to our renovated lake house nestled on a 3/4 acre treed lot, naturally treated for mosquitoes and ticks. Enjoy the tranquil serene atmosphere while being close to picturesque tobacco fields.
Popular amenities for Windsor vacation rentals
Other great vacation rentals in Windsor

Designer's Den in the Business District

Cozy, spacious apartment w/ balcony & free parking

By The River

Relax By The Water

Island Vibes

Bloomfield Bungalow

Quiet Comfy Getaway 3 BDR home

Newly Renovated 2 Bedroom in Heart of Tariffville
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R2,020 ZAR | R2,142 ZAR | R2,090 ZAR | R2,351 ZAR | R1,968 ZAR | R1,828 ZAR | R1,898 ZAR | R2,090 ZAR | R2,212 ZAR | R2,107 ZAR | R2,177 ZAR | R2,299 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
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.
Where should I stay in Windsor?
Make yourself at home in Windsor by choosing from our most frequently booked neighborhoods. We have over 70 vacation rentals in Windsor Locks, and over 20 vacation rentals in Hayden.
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.
What are the most popular amenities for House Rentals in Windsor?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 40 homes with wifi, over 30 homes with a kitchen, over 40 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
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.
Are there vacation rentals with a dedicated workspace in Windsor?
Yes! Work meets play with ease at over 40 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive 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.
Quick stats about vacation rentals in Windsor

Total vacation rentals
Explore 60 vacation rentals in Windsor

Nightly prices starting at
Windsor vacation rentals start at R348 ZAR per night before taxes and fees

Verified guest reviews
Over 2,070 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
40 properties have a dedicated workspace

Wi-Fi availability
60 of Windsor vacation 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
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