Holiday houses in East Hampton

Your Own Barn Loft Suite Among the Treetops

Forget your worries in this spacious and serene space. You’ll arrive through your own driveway, park in your own spot and enter through a private entrance. Make yourself at home whether a weekend get away or traveling for work you’ll feel very relaxed. 250’ from the airline trail, walk or bike right into downtown East Hampton for a coffee in the morning or set out on the 30 + mi trail to enjoy your true country getaway. Head into Middletown to enjoy many restaurants, bars or clubs. *NOTE PET FEE

Location · Family · Biking

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.

Location · Family · Bathroom

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.

Family · Value · Heating

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.

Value · Location · Comfort

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

Location · Hospitality · Sleep quality

CT River Retreat - Modern Home with CT River Views

Welcome to your home away from home! This charming three-bedroom, three-full-bath house is the perfect retreat for your stay in or near East Hampton, CT. Explore the charm of the area with ease, as the house is conveniently located .1 mile away from Saint Clements Castle & Marina, and 7 miles from Wesleyan University. Nestled along the picturesque Connecticut River, this inviting haven offers not only comfortable accommodations but also stunning views that will leave you breathless.

Location · Family · Bathroom

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Family · Value · Condition

Historic Hearthstone Cottage

Built in 1800 and thoughtfully renovated in 2024, this two-story guest cottage can be the retreat of your dreams. Surrounded by thousands of acres of nature preserve, short walks to scenic vistas, a raging waterfall and countless hiking trails, few places are as peaceful as Hearthstone. Whether you’re looking for a private oasis or romantic getaway, are a parent sharing the beauty of nature, or an artist looking for inspiration, this historic cottage is for you.

Location · Family · Access

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.

Family · Location · Pets

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)

Location · Value · Pool

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!

Value · Family · Amenities

Direct Waterfront Cottage on Moodus Reservoir.

Relax with the whole family at this peaceful place to stay with direct access to the lower Moodus Reservoir. The backyard leads out to the lake with a small beach area (fits approximately two lawn chairs). Sit on the patio by the fire pit and enjoy the view or grab a kayak, pedal boat, or paddleboard and enjoy your time directly on the lake.

Family · Location · View