Family-friendly holiday rentals in East Hampton

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.

Breathtaking home with unforgettable views & pool!

This spacious peaceful and private home on 5 acres is great for unwinding & relaxing whether it is enjoying the day by the incredible pool/spa or stargazing at night. Far from the noise and pollution of city life. You can spend a weekend or a week away from work life because you deserve it. Close to Foxwoods casino and Mohegan sun casino, super Walmart and other stores. Please let us know before booking more than 4 people whether it is just for the day or night or both. No loud music no parties.

Family Stays, CT

Centrally located - just 1.2 miles from Wesleyan University, this home offers comfort, convenience, and generous space for groups. With 4 bedrooms across two floors, the layout lets everyone spread out. Bedrooms on separate levels provide natural privacy while still enjoying one shared home. Whether you're traveling with friends, children, extended family, or multiple couples, the 2‑floor setup helps everyone relax without feeling crowded. Ideal for multi‑generational stays and group getaways.

Luxe Bolton Lake

Stay at Luxe Bolton Lake and feel like you are a million miles from home! The Luxe features a BEAUTIFUL WATERFRONT, 3 bedrooms/3 full bathrooms and a year-round outdoor JACUZZI Also included: gorgeous primary bedroom suite, artistic furnishings, cozy FIREPLACE, coffee bar, complimentary snacks, speedy WiFi, large deck, fire pit, KAYAKS, board games, and much more. The Luxe is perfectly suited for families and guests of all ages, so come stay at Luxe and make memories that will last a lifetime!

Beautiful lakefront home, 4bed 2.5ba

80ft of lakefront. Perfect for summer water activities, stunning fall foliage and ice skating in the winter! East-facing with stunning sunrises. Very well equipped kitchen, cosy sitting room & wood-burning stove, dining room and 1/2 bath. Large porch faces lake, with sitting area and dining table. Ground floor king-size master & bathroom, with stunning lake views. Upstairs 3 queen bedrooms, all w lake views and ample closet space. TVs in 3 bedrooms + projector/screen for movie watching.

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.

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.

Casino Stay & Play House w/Hot Tub, Game Room

Come have an unforgettable vacation at our fun-packed home! The house is loaded with of games and conveniently located close to Mohegan Sun, Foxwoods, Mystic, Vineyards, Navel Submarine Base, Ct College and several beaches. Enjoy our game room where you can sing karaoke, play over 3,000 classic games and draw on our giant chalk board wall. Outside enjoy swimming in your own private pool, take dip in the hot tub, play a game of corn hole and watch tv by the fire pit on the deck

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.

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

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)

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.