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.

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Guest favorite
A spacious living area is presented, featuring a comfortable gray sectional sofa, a wooden coffee table, and a decorative rug. Two green bar stools are positioned at a small counter, and a ceiling fan is mounted above, enhancing the cozy atmosphere of the penthouse apartment.
Home in West Hartford
4.89 out of 5 average rating, 112 reviews

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.

Superhost
A well-appointed sleeping area features a spacious bed with crisp white linens and decorative pillows. Two comfortable chairs are positioned around a circular table, complemented by a potted plant and a cozy blanket draped over one chair. Large windows allow natural light to fill the room.
Apartment in Downtown Hartford
4.89 out of 5 average rating, 208 reviews

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.)

Superhost
A bright workspace features a wooden desk with a black chair, positioned against a light-colored wall. Two framed botanical prints are displayed above the desk, complemented by a standing lamp. A mirror reflects the scene, while a potted plant adds a touch of greenery.
Apartment in Windsor Locks
4.84 out of 5 average rating, 178 reviews

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

Guest favorite
A spacious living area is furnished with a gray sectional sofa, accented with colorful throw pillows. A wooden coffee table is placed in front, on a soft area rug. Two large windows allow natural light to brighten the room, complemented by ceiling fans and tasteful decor.
Loft in Tolland
4.96 out of 5 average rating, 284 reviews

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!

Top guest favorite
A cozy living room features a stone fireplace surrounded by purple walls. A wooden table sits at the center, adorned with a decorative bowl. A comfortable sofa and a wooden chair are positioned near the fireplace, complementing the warm ambiance.
Cottage in Windsor
4.9 out of 5 average rating, 196 reviews

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 favorite
The inviting living area features a door leading to the patio, allowing natural light to fill the space. A wall clock and TV are positioned on gray walls, complemented by a coffee table and cozy seating. Views of the green outdoors can be seen through the windows.
Guest suite in Bloomfield
4.98 out of 5 average rating, 124 reviews

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.

Guest favorite
A comfortable sleeping area features a dark tufted headboard and a soft, neatly arranged bedding with multiple pillows. A lamp is positioned on a bedside table, while a floor lamp provides additional light. A floral wall art piece adds a subtle touch above the bed.
Home in Manchester
4.94 out of 5 average rating, 221 reviews

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.

Top guest favorite
The exterior of a historic brick house is showcased, featuring a rounded turret and a welcoming front porch. Lush greenery and colorful flower beds surround the entry stairs, which lead to the front door. A small garden area adds to the inviting atmosphere of the home.
Loft in Frog Hollow
4.99 out of 5 average rating, 737 reviews

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.

Guest favorite
A brick patio area is seen with two rocking chairs positioned beside vibrant orange and yellow flower pots. A welcoming wreath adorns the double doors, and a pumpkin is placed on the ground, enhancing the seasonal decor.
Guest suite in East Granby
4.86 out of 5 average rating, 387 reviews

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

Top guest favorite
A spacious living area is shown, featuring a beige sofa and a patterned armchair. The kitchen with stainless steel appliances is visible in the background, alongside a dining table. Warm wooden floors and soft lighting contribute to a comfortable ambiance.
Guest suite in West Hartford
5 out of 5 average rating, 238 reviews

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.

Top guest favorite
A bright living area features a dark sofa with multiple cushions, flanked by two patterned chairs. A wooden coffee table is positioned in the center, and a laptop is placed on it. Natural light enters through the two windows, adorned with dark curtains.
Apartment in Enfield
4.99 out of 5 average rating, 281 reviews

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.

Top guest favorite
A charming lakeside cottage is nestled among trees, featuring a stone pathway leading to its welcoming yellow exterior. A circular stone fire pit is surrounded by green foliage, and picnic tables are placed on the grassy area, creating a serene outdoor setting.
Home in West Suffield
4.96 out of 5 average rating, 113 reviews

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

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR2,020 ZARR2,142 ZARR2,090 ZARR2,351 ZARR1,968 ZARR1,828 ZARR1,898 ZARR2,090 ZARR2,212 ZARR2,107 ZARR2,177 ZARR2,299 ZAR
Avg. temp-3°C-1°C3°C10°C16°C20°C24°C23°C18°C12°C6°C0°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