Vacation rentals with outdoor seating in Haddam

Chester Cottage Waterfall House

A Bright Dreamy Colorful Warm Little House. The kind of spot to look at the stars at night and enjoy the sound of running water. Surrounded by Waterfalls, Rivers & Forests, close to Ferryboats, Steam Trains, Castles & Beaches. Five min stroll to Romantic Chester Village, Shops, Art Galleries, 9 Restaurants, and Microbrewery. . I am an artist and have my studio in the barn! (take a peek to see the latest sculptures ) Use our Glass House by the river for Yoga, Meditation, Dining, Hammocks

The Millhouse Downtown Chester

An upscale destination with accommodations for foodies & friends in the heart of historic Chester CT. Stay at this beautifully renovated historic Millhouse in charming downtown Chester. Enjoy strolling the streets loaded with shops, award winning restaurants, a microbrewery, art galleries, and more. All within a 1 minute walk. Our prime location is just 20 minutes to the CT shoreline and located in the heart of the CT River Valley. The Millhouse is next door to the Chester Historical Museum.

Charming Chester Retreat - Cottage

Ready for Summer? Beach Access! This 2 bed, 1 bath unit has been redesigned to feature a modern kitchen, soaking tub and wood-burning fireplace. The unit also features 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! New England getaway / Hidden Gem / Retreat/ Beach Access

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.

Cozy Mid Century home in prime location!

Enjoy an updated, mid century modern inspired, home minutes away from Wesleyan University & TPC River highlands! This eclectic space offers you a cozy retreat that is centrally located. The bedrooms have 1 King, 1 Queen, & 1 Full with luxury mattresses! High speed Wi-Fi, chefs kitchen, dedicated work desk, and garage space! A few mins from RT 9 & 91! Easy to get everywhere in CT!!! Only 5 mins to TPC, 10 mins to Wesleyan, 20 mins to Hartford! Scald protector on shower upstairs!

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

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.

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.