Vacation rentals in Windsor

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

Home in Asylum Hill

4.77 out of 5 average rating, 70 reviews

The Silhouette in Hartford

Welcome to your ideal getaway from SUBURBIA! During your stay, enjoy a peaceful, relax atmosphere perfect for work, reading or simply unwinding. Then feel the energy shift especially on the weekend with the soulful rhythms Caribbean music that add a unique local flair. Nestled close to the heart of the capital, our location gives you easy access to everything for a city life while enjoying a quiet retreat. Book now for an authentic Airbnb experience where tropical vibes meet true tranquility.

Superhost

Apartment in Windsor Locks

4.85 out of 5 average rating, 173 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

Home in Windsor

4.93 out of 5 average rating, 80 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.

Guest favourite

Home in Windsor

4.92 out of 5 average rating, 66 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

Home in Windsor

4.97 out of 5 average rating, 60 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!

Guest favourite

Home in Windsor

4.96 out of 5 average rating, 53 reviews

By The River

Forget your worries in this spacious and peaceful space. Walking distance to a great restaurant. 6 minutes drive to the Bradley Airport, shopping and entertainment. Our guests get free membership to the indoor Tennis and Pickleball in Windsor and Manchester! This location however, is not available to host parties or other group events. This is a very quiet neighborhood. No smoking and no pets, no exceptions. Property has security outdoors cameras.

Guest favourite

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 favourite

Guesthouse in Enfield

4.96 out of 5 average rating, 53 reviews

Close AirPort|SixFlags|Big E|Free Private Parking

Escape to Pineside Retreat in Enfield, CT—a tranquil haven blending comfort and nature. Conveniently located 20 minutes from Bradley Airport and MGM Springfield Casino, 15 minutes from Six Flags, 22 minutes from Holyoke Mall, 5 minutes from Scantic River State Park, and 10 minutes from Windsor Locks Canal State Park. Perfect for professionals or adventurers seeking relaxation in a cozy, rustic-modern retreat.

Top guest favourite

Loft in Frog Hollow

4.99 out of 5 average rating, 726 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

Guest suite in East Granby

4.85 out of 5 average rating, 373 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 favourite

Apartment in Enfield

4.99 out of 5 average rating, 266 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.

Superhost

Apartment in West Hartford

4.85 out of 5 average rating, 121 reviews

West Hartford Center Apartment

Spacious 1 bedroom 1 bathroom apartment with a private entrance. A 10 minute walk from Blueback square, Whole Foods Market & more. Kitchen fully furnished, high speed internet, private balcony, 86 inch smart TV, in a quiet and safe neighborhood. Washer and dryer in apartment, free driveway parking. Pets allowed