Holiday rentals in Uncas Pond

The Little Chestnut.

Located in Chester Village, this historic hideaway is buffered by the village parking lot and a running brook offering in-village convenience with natural serenity. Located above a delightful bookstore, thriving Main St is just seconds away complete with excellent restaurants, boutique shopping, and art galleries. The grounds are filled with floral planters with a wonderful little park across the brook. A picnic table and gazebo for your enjoyment. Last-minute one-night stays, please message us.

New Listing - Charming Classic Cottage Style Home

Quaint, charming New England home. Safe, quiet location in historic Old Lyme with public beaches, tennis, basketball, sailing, kayaking nearby. Close to artistic roots of Old Lyme, Florence Griswold Museum, & jazz evenings at the Old Lyme Inn. Close access to all major thruways (I-95), high-speed rail (Amtrak), ferry, minutes away from Essex CT, Old Saybrook, scenic Mystic Seaport, & Mohegan Sun casino. The Space: Fully air-conditioned; Indoor Decorative Fireplace; Washer/Dryer; Sun Room, 2 bed

New! “LaBoDee”

“LaBoDee”, a fun play on the word abode, house, is a tiny cottage located central to CT’s unique shoreline communities, just off I95. “LaBoDee” is one room with a fully equipped kitchenette, ready for those who would like to stay awhile. “LaBoDee” is on a property contiguous to a state forest (a trail is right outside the door) yet within walking distance is a delicious deli, market, gas station, pizza, a lake, and close by is the beach. A local restaurant has day passes for their beach- $20!!

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.

Water Forest Retreat- Tree House

Water Forest Retreat Tree House is a 168 sq ft. private heated and electrified tiny home with stained glass windows surrounding an oak tree nestled on 56 acres of forest. Enjoy your favorite drink out on the deck up in the trees while watching the birds. There are 2 1/2 miles of hiking trails with a brook, waterfall, marsh and pond. Come here to hike, fish or just relax in this beautiful forest. We also have an OCTAGON and HIKER’S HAVEN house. Please click on our profile picture to read more.

Quintessential Essex. Steps from the Steam Train!

Enjoy a stylish experience at this centrally-located apartment. This 2 bedroom unit boasts plank flooring and tons of natural light! Kitchen has stainless appliances, granite countertops and subway tile backsplash. Large living room with many windows, tiled shower with modern vanity, spacious bedrooms and gorgeous sunroom overlooking the Essex Steam Train! Short walk to Sayulitas and the Cheese Shop of Centerbrook. Short ride to Essex Village, the Ivoryton Playhouse, and the CT Shoreline!

Tinker Gardens

Take a break and unwind at this peaceful oasis, nestled among English-style gardens. A quiet country escape from the hustle and bustle of city life, Tinker Gardens is a cozy private cottage full of character (including murals by a local artist). Adjacent to the Nehantic State Forest in the stunning countryside of Lyme, there are numerous trails to hike or bike and a lake to swim or kayak. There is easy access to beaches and some of the best restaurants in Southeastern Connecticut.

Hot Tub & Cloud Ceiling House 5 min to Mohegan Sun

Stay at a one-of-a-kind house located 5 minutes from Mohegan Sun and several other attractions close by. Our house is conveniently located close to Foxwoods, Mystic, vineyards, Navel Submarine Base, Ct College, USCG Academy and several beaches. Enjoy our game room where you can play arcade games, pool, foosball, giant connect 4, hooky, board games and sing karaoke all under a light up cloud ceiling. Relax in the hot tub or by the gas fire pit in our private backyard.

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.

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.

Rogers Lake House (87) · CT College+Beach+USCGA

The house features three bedrooms, two bathrooms, a spacious kitchen, and a comfortable living room with multiple outdoor seating areas. We feature one bedroom downstairs and two bedrooms upstairs. The first floor bedroom has direct access to outdoor seating, perfect for enjoying your morning coffee. Walk across the street to the boat launch and enjoy all that Rogers Lake has to offer.

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!