Vacation rentals in Windsor

HideAway UConn Coventry RockFarm BnB Breakfast A+

Welcome to “The Hide Away” on Rock Farm with Superhosts Jon & Jeri. A private, family-friendly 1000+ sq ft wooded retreat featuring two bedrooms, 500 Mbps WiFi, Roku TV, private deck, full kitchen, laundry, and DIY breakfast. Just 15 minutes to UConn and 2 minutes to Bolton Lakes for fishing and hiking. See our VIP Guest Book for local favorites. Clean, cozy, no-shoe secluded BnB — 5⭐️ guest favorite. Ask about “The GetAway” too! It’s our King Studio Suite, a private space, perfect for couples.

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Private Cozy Suite, 0 Fees, Pets Welcome, EV Plug

A private cozy suite for you! Better than a hotel or private room & less than an entire house. Pets welcome with no fees :) Generous discounts for medium- to long-term stays. Your guest suite includes newly furnished living room, apartment kitchenette, large bedroom with full bathroom. Despite many renovations, we kept the vintage & cozy charm. Keurig machine. Separate Wifi for remote work. Less than 20 minutes to the airport and Hartford metro. No cost EV charger on site. No cleaning fees!

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!

Mountain Retreat close to Northampton & Amherst!

Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

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.

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

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 😊.

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

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.

Treehouse - Countryside - Farm Animals - Fire Pit

Escape to the stars in the Private Treehouse nestled among the trees at Bluebird Farm Connecticut. Amenities: ● 100+ Mbps Wi-Fi | Outdoor Fire Pit | Indoor Fireplace ● Interaction w/ Farm Animals | Year-Long Running Water (Sink/Shower) ● Kitchenette | AC in Unit | Free Coffee | Board Games | Books Drive To UCONN (10 Mins) | Hartford (30 Mins) | Boston (1 Hour) | NYC (2.5 Hours)