Holiday rentals in Marlborough

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

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Lake Cottage Getaway

Leave your worries behind and enjoy the breath-taking view of the Great Hill Pond Lake with your own private dock! Relax on the lake and enjoy your favorite drink. This 500 sq ft cottage offers an updated kitchen, bathroom, master bedroom with full size bed, living room, sunroom & outdoor gazebo overlooking the water. Perfect for a romantic getaway, writer's retreat, or a nice getaway to just unwind and enjoy the beauty of nature. Great nearby trails & about 15 minutes to downtown Middletown.

Beautiful Lake House on Lake Pocotopaug

Enjoy a relaxing vacation in a beautiful, updated lakefront home on Lake Pocotopaug. Summer =grilling out, kayaking & paddle boarding with family & friends. A lakeside marina offers party boat rides & kayak rentals. Winter=relaxation by the cozy fireplace, games and ice skating when the lake freezes over. Projector Screen, Games, Books, AC, Heat, Outdoor Grill and a working fireplace. All year round, we'd love to have you at our home. which we love and use as a getaway from the city.

Lake Me Home

Relax and unwind at this cozy lake home, thoughtfully stocked with everything you need for a memorable stay. Direct Waterfront access easy access to a fantastic lake Offering Paddle Boat use,kayaks,paddle board dock access. This lake you can boat to down town shopping,restaurants offering dock and dine. Inside, the home is fully equipped with games, quality cookware, comfortable bedding, and a convenient laundry area. It’s the perfect spot to spend quality time.

Lovely, peaceful lakefront home.

Relax with the whole family at this peaceful lakefront house. Swim and fish from the dock. Explore the lake in kayaks or the canoe, toast marshmallows at the fire pit. Curl up with a book and/or a cocktail in the den/bar/library. Cook a gourmet meal in the kitchen or kick back and grill outside. Hike the trails in the 100 acre land trust across the street. Shop and dine in the charming village center. Wind down and relax in a truly tranquil space.

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Charming Barn Apartment

Our one bedroom apartment in a colonial barn has a country feeling but is a 10 minute drive into downtown Hartford, and halfway between Boston and New York City .There are woods on one side and from the living area look out on a hillside where you can sit for a spell or spend some time on the private stone patio right outside the door. There are beaches and casinos within an hours drive.

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)

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

Rustic Farmhouse by the River (Duplex)

This renovated apartment is the perfect getaway. Enjoy all that our family farm has to offer, take a walk down to the river, or explore some of the amazing attractions in South Glastonbury. This is the perfect place for a weekend trip or a longer term stay.