Holiday rentals in Deep River

The Little Chestnut: Walk to downtown Chester.

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.

Serene Waterfront Cottage

Welcome to Smuggler’s Cove Cottage. Rumor has it that this quaint cottage was once the scene of infamous rum running. Today, it’s our little slice of heaven away from the chaotic city life. It’s the perfect place to curl up and read a book by the fire when it’s chilly out. During the warmer months, take full advantage of the spacious waterfront patio & docks. Whether you’re sunbathing or having a drink watching the local geese and ducks float by, this tranquil cottage has everything you need.

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.

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!

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

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.

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!