Family-friendly holiday rentals in Windsor

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,

Top guest favourite

Guest favourite

Prime West Hartford Center Location: Historic Gem

With over 500 five star guest reviews, Mark Chu Rentals is known for exceptional hospitality, thoughtful details, and memorable stays. Enjoy the perfect blend of historic charm and modern comfort in the heart of West Hartford Center. Relax on the spacious private deck with a gas fire pit and grill, or take a short walk to Blue Back Square for boutique shopping, restaurants, cafés, and entertainment. The nearby Delamar Hotel makes this an ideal location for business and leisure travelers alike.

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

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 an stress-free experience 😊. **NO SMOKING of any kind (including cigarettes, vaping, e-cigarettes, marijuana, or any substances).

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. Per-person pricing. Please select the correct number of guests when booking.

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.

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.

Charming Cape Home, Close to All

Charming Cape Home in the Heart of Connecticut Enjoy comfort and convenience just 20 mins from Bradley Airport, 10 mins from Hartford, 25 mins from UConn, and 40 mins from New Haven. Nestled on a quiet residential street, our cozy home features multiple beds, fast Wi-Fi, Smart TVs, central air, and a fenced backyard with patio and fire pit. Grocery stores, restaurants, and coffee shops are just 5 minutes away. A perfect retreat for families, professionals, or campus visits!

Top guest favourite

Guest favourite

Farm Stay with Horses & Pool | Mountaintop Views

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Bask in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

10 Hillcrest

So we were offline for a few months but we now have a totally new remodeled space. Lots more light and upgrades we think you will enjoy! 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! Many, many farms, wineries, breweries and eateries just minutes down the road. We are also just minutes from Bradley International Airport

Top guest favourite

Guest favourite

Quiet Comfy Getaway 3 BR Home | Close to BDL

Welcome to our newly renovated 3-bedroom home in Windsor, CT! Sleeps up to 8 guests and is perfect for families, business travelers, healthcare professionals, and extended stays. Enjoy fast WiFi, a dedicated workspace, fully equipped kitchen, complimentary coffee bar, washer/dryer, free parking, and spacious bedrooms. Minutes from Hartford, Bradley Airport (BDL), hospitals, shopping, dining, and major highways.

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.