Holiday houses in Haddam

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Family · Location · Outdoor spaces

Family Stays, CT

Centrally located - just 1.2 miles from Wesleyan University, this home offers comfort, convenience, and generous space for groups. With 4 bedrooms across two floors, the layout lets everyone spread out. Bedrooms on separate levels provide natural privacy while still enjoying one shared home. Whether you're traveling with friends, children, extended family, or multiple couples, the 2‑floor setup helps everyone relax without feeling crowded. Ideal for multi‑generational stays and group getaways.

Value · Family · Getting around

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.

Value · Location · Hiking

East Haddam Village | Walkable, Pet Friendly

Creamery Road Karczma is a 1850 farmhouse in the heart of East Haddam Village, just steps from the Goodspeed Opera House and the Connecticut River. Walk to restaurants, and local shops, or stroll down to the river, public boat ramp, and views of the iconic Swing Bridge. A peaceful village stay with a country feel, featuring chickens on-site and pet-friendly. Ideal for those attending events at The Riverhouse at Goodspeed Station or Smith Farm Gardens, or enjoying a getaway near the river.

Location · Family · Kitchen

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.

Location · Family · Amenities

Summer at the Haddam House

You cannot miss this beautifully renovated waterfront 4 season cottage in Haddam with stunning views of the East Haddam Swing Bridge, Goodspeed Opera House and The Gelston House. Watch float planes come in and out from the certified landing strip on the CT River. There is a deep water dock for larger boats and a "No Wake" zone to further enhance the peace and tranquility of your private spot. Enjoy your own private beach, patio with firepit and step down dock for provided kayaks.

Family · Location · Biking

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Location · Value · Access

Historic House by the River

No matter the reason for your stay, this house is a great choice! Located in the center of town just steps from the Goodspeed Opera House, Gelston House, Goodspeed Airport and public boat ramp. Enjoy amazing views of the Swing Bridge and the Connecticut River. It is just a short walk from local coffee shops, restaurants, and shopping. There is plenty of historic charm from the wavy original wood floors, 1800's style steep staircase, and original antique finishes.

Family · Location · Indoor spaces

The Doll House

Enjoy the Connecticut River Valley at this cozy retreat close to where you want to be. Conveniently located near Route 9, the Doll House is easy to get to from Middletown, the shoreline, and Central CT. Enjoy the patio while having dinner or just taking in the outdoors. Take advantage of all the area has to offer, from hiking, to shows at the Goodspeed Opera House, and fine dining options in Downtown Middletown. Enjoy this private setting surrounded by nature.

Family · Location · Backyard

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.

Location · Family · Quiet

Quarry House: Mid-Century Modern

Perched atop a hill and nestled among lush woods, Quarry House is a stunning Mid-Century Modern home offering a unique blend of style, comfort, and history. Originally a granite and quartz rock quarry, the property still showcases the natural stone that once defined its past, providing a truly one-of-a-kind setting. Located in the peaceful town of Haddam, CT, this home is perfect for those looking to escape while still being close to the action.

Location · Family · Kitchen

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

Value · Location · Air conditioning