Vacation rentals in Essex

Historic 2 BR, quick walk to downtown Essex!

Keep it simple and relax in a centrally-located second floor apartment in our historic, near town, home. Enjoy the outdoor porch, work a tad in the light-filled office, or make a meal in our fully-stocked kitchen. We are experienced 5 star Airbnb hosts with our property in Guilford CT and delighted to offer this new space to guests looking to enjoy the charm of Essex. 5 min walk downtown, 15 min walk (3 min drive) to the Essex Steam train. So much to enjoy in the CT river valley & shoreline!

The Dragon Fly Garden

The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet

Chester Gingerbread House: Stroll to Village

Escape the city to this whimsical retreat, just a short stroll from downtown Chester. With three stylish bedrooms, plush beds, and spa-inspired bathrooms, it’s the perfect getaway for friends, couples, or families with older kids. Unwind in the private garden, wander into the village for shopping or dining, or work peacefully in the dedicated office/study. Just 10 minutes from I-95, this serene hideaway blends historic charm, modern luxury, and everyday convenience for an unforgettable stay.

Cheerful, private cottage in Essex village.

Take a break & relax at this peaceful, private cottage tucked away in historic Essex Village. One of the most desirable locations in Essex. Your getaway is within walking distance to downtown shopping, restaurants, riverfront marinas as well as town parks, tennis courts, the Library and land trust properties. Come enjoy all that Essex has to offer, all while relaxing in your own private retreat. NOTE- if you need additional space for guests, we have another Airbnb next door-see photos.

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!

Adorable 2 bedroom guesthouse in Essex village

Enjoy the best of both worlds with this remodeled 2 bedroom and 1 bath antique home located on the coveted North Main Street in Essex Village. You are close enough to walk downtown (0.8 miles) but away from the hustle and bustle. The park-like back yard with an antique trolley bridge and Falls river running through it will give you the perfect place to unwind after a day of activities. Come see why Essex was named “The Perfect Small Town" in the book 1000 Places to See Before You Die!

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.

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.

Ideal Historic Home in Essex Village

Welcome to village life in the heart of Essex Village. This is the longest running and most visited vacation rental home on Main St in Essex, CT. 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.

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!

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.