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.

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 lakefront home, 4bed 2.5ba

Fully renovated, on 80ft of lake front. Perfect for summer water activities, stunning fall foliage and often ice skating in the winter! East-facing with stunning sunrises. Very well equipped kitchen, cosy sitting room with wood-burning stove, dining room for 8, and powder room. Large porch faces the lake, with a sitting area, and dining table for 8. Ground floor king-size master & bathroom, with stunning lake views. Upstairs, 3 queen bedrooms, all with lake views and ample closet space.

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

Classic Lakehouse~Fire Pit_Canoes_Kayaks & Sunsets

Private lakefront home on Lake Pocotopaug with a fishing dock, kayaks, fire pit, and spectacular sunset views — perfect for family & friend getaways. Welcome to Lakeside Ferns, where you’ll enjoy direct waterfront access and private dock for swimming, fishing, kayaking, canoeing, and boating. Grill dinner, relax in the hammock by the water, and gather around the outdoor fire pit for s’mores under the stars. End each day with breathtaking sunsets over the lake — beautiful in every season.

Classic Farm House on a Working Farm & Vineyard

This quaint farmhouse will be your home away from home. Enjoy the scenery and explore local attractions. The farm house is situated just feet from Joseph Preli Farm and Winery (also owners of the farmhouse) with its bountiful grapevines, fruits and vegetables. The farm and vineyard is known for it's old-world Italian charm. Family owned for 100 years, they respect history by using traditional farming methods and antique tractors. See updates about the farm and winery at @jprelifarm

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!

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.

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.

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.

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!

Bashan Lake Bungalow

Welcome to the Bashan Lake Bungalow! This charming, newly renovated cabin is designed for a relaxing, stress-free stay. Nestled in the heart of East Haddam, Connecticut, and surrounded by scenic state parks, the Bungalow offers beautiful views of Bashan Lake. Spend your time here unwinding, hiking the nearby trails, or simply enjoying the peaceful surroundings.