Holiday rentals in Essex

Ideal Historic Home in Essex Village

Welcome to your opportunity to live the village life and stay in the heart of Essex Village. This is the first time a vacation rental home on Main St in Essex, CT has been listed on Airbnb. Chosen as the best small town in America by Norman Crampton in his book, The 100 Best Small Towns in America. Essex also appears in 1000 Places to Visit Before You Die. Located on the Connecticut River, this friendly New England community has been welcoming travelers since before the American Revolution.

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

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!

Water View Mid Century Home in Essex CT, 4 Kayaks

Welcome to FALLS RIVER, Essex CT! The house is located in a well established, quiet & charming New England neighborhood on a scenic road, few min from Essex Village! This mid-century house offers 4 bedrooms, 2.5 bathrooms, 1 outdoor shower, a movie room, meditation loft and an outdoor deck (dry bar, grill) to enjoy the water view. You also have access to 4 kayaks. Nature and animal lovers will appreciate the views, birds symphony and the quick access to multiple nature trails.

Charming Chester Retreat - Cottage

*Summer's Here** Book your Cottage stay minutes from Chester's town beach: This 2 bed, 1 bath unit has been redesigned to feature a modern kitchen, soaking tub and wood-burning fireplace. The unit also includes a roof deck that overlooks our mature maple trees and a sprawling front porch, complete with rockers. Beach Access 10 min away at Cedar Lake. Great for 1-2 couples, small families or group of friends—Ask about our single roll away bed or pack' n' play(s). Kid friendly!

Lovely Garden-Level Apartment in Heart of Town

This garden-level apartment is centrally located within walking distance to Main Street's retail shops, restaurants, and grocery/pharmacy, and just minutes from The Lace Factory and Deep River Landing, Essex Steam Train & Riverboat, Connecticut River Museum, the CT shoreline and beaches, and so much more. A charming historic home over 200 years old with a classic New England feel, the apartment has two bedrooms, one full bath, and an eat-in kitchen complete with amenities.

The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK

Located in charming downtown Chester, our loft rests above the newly established Village Bistro; with the loft being situated above our restaurant and on Main Street please keep in mind that you may hear some background noise during normal business hours. Additionally, you will be staying in a 200-year-old structure so there is some quirkiness that goes along with an aged building such as ours but rest assured you will feel right at home in this cozy, warm, historic space.

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.

Chester Village 'Pied-à-terre' above art gallery

Our lovely apartment is well designed in an ideal location. A sunshine filled living room w/high ceilings, a private bedroom in back, and large private deck overlooking Pattaconk Brook. A true gem, set up solely for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique. We're neighbor to some of the BEST restaurants, art and shopping in CT! We know you'll enjoy your stay!

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!

The Nest

Our warm and inviting studio apartment with bright and cheery decor offers a cozy get away any time of year. Nestled in a peaceful country neighborhood with endless hiking trails, beaches, and cozy villages nearby. The Nest offers a comfortable and convenient place to stay while enjoying the surrounding area.

Modern Farmhouse with Hot Tub in Old Lyme, CT

Originally built in 1856 this farmhouse has been lovingly restored with stylish and modern amenities for a perfect vacation getaway. Nestled in the heart of downtown, historic Old Lyme the property is convenient to shops, restaurants and local shoreline activities including water sports and hiking.