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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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, 214 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, 180 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 favourite
Guest suite in Bloomfield
4.92 out of 5 average rating, 117 reviews

Private Cozy Suite, 0 Fees, Easy CheckIn, EV Plug

A private cozy suite for you! Better than a hotel or private room & less than an entire house. We do not charge extra fees! Sizable discounts for medium- to long-term stays. Your guest suite includes newly furnished living room, apartment kitchenette, large bedroom with full bathroom. Heating, cooling and hot water are all-electric. Despite many renovations, we kept the vintage & cozy charm. Separate Wifi for remote work. Less than 20 minutes to the airport and Hartford metro. EV charger!

Top guest favourite
A spacious living area features high ceilings with exposed beams and wooden flooring. Comfortable seating includes sofas and chairs arranged around a central coffee table. A large television is set against one wall, and plants add a touch of greenery to the room.
Home in Windsor
4.93 out of 5 average rating, 90 reviews

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.

Top guest favourite
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.

Top guest favourite
A spacious living area features a large sectional sofa adorned with decorative pillows, offering comfortable seating. Large windows allow natural light to fill the room, highlighting the wooden floor and a coffee table at the center. A warm ambiance is complemented by tasteful artwork on the walls.
Home in Windsor
4.93 out of 5 average rating, 85 reviews

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!

Top guest favourite
A stone exterior corner of the home presents a covered porch with white railings. The adjacent grassy area leads to a serene river view, where trees surround the water's edge, reflecting the soft light of the sky.
Home in Windsor
4.97 out of 5 average rating, 66 reviews

Relax By The Water

Take it easy at this unique and tranquil getaway. Just 20 minutes from downtown Hartford, 5 minutes from Bradley airport, and conveniently close to the Loomis Chaffee school, you’ll have our entire two bedroom, two bath riverfront home to enjoy. Take in the views from the expansive balcony, enjoy a meal in the waterside dining room, or work from home in the dedicated office space. Two queen beds and a sleeper sofa sleep six comfortably. Don’t miss it!

Top guest favourite
Apartment in New Britain
4.96 out of 5 average rating, 239 reviews

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Top guest favourite
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, 749 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 favourite
A spacious outdoor area is showcased, featuring a well-maintained lawn and a wooden deck leading to a white, single-story house. Surrounded by trees, the private yard includes a white picket fence, providing a sense of seclusion.
Guest suite in South Windsor
4.86 out of 5 average rating, 227 reviews

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 😊.

Superhost
The exterior of a charming red schoolhouse and accessory building is surrounded by vibrant foliage. A white wooden fence outlines the property, leading to a gravel pathway. The buildings feature classic architectural details, with windows framed in white and a backdrop of lush trees.
Cottage in Granby
4.86 out of 5 average rating, 233 reviews

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.

Top guest favourite
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, 290 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.

Popular amenities for Windsor vacation rentals

When is the best time to visit Windsor?

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Frequently Asked Questions

  • Where should I stay in Windsor?

    Make yourself at home in Windsor by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in Hayden, and over 70 vacation rentals in Windsor Locks.

  • 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.

  • 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.

  • 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 wifi, over 30 homes with free parking, over 30 homes with a kitchen, over 30 homes with air conditioning, 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 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.

  • Do house rentals in Windsor have wifi?

    Absolutely! We offer over 30 house rentals with wifi 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.

  • Do house rentals in Windsor have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Windsor. Enjoy a tailored experience with all the comforts you desire.

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 $27 CAD 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 and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of Windsor vacation rentals include wifi 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