Vacation rentals in Haddam

4.79 out of 5 average rating, 284 reviews

A cozy living area features a gray sofa and ottoman, complemented by an artistic wall decoration. A spiral staircase leads to a lofted space above. Natural light streams in from the window, highlighting the exposed beams and the elegant architecture of the room.

Apartment in East Haddam

The Federal Suite at the Wisteria Rest

The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining. This apartment is in the 1800 section and has some quirky things to be aware of, floor that have uneven heights, stairs to the bedroom and , a claw foot tub/shower that you have to step into and a full flight of stairs to get in.

4.93 out of 5 average rating, 371 reviews

The kitchen area includes a sleek granite countertop with two wire-frame stools positioned underneath. Natural light enters through the adjoining living space, highlighting the warm wooden flooring. Sliding glass doors lead to a bright living room, creating a sense of openness and connection.

Apartment in Chester

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

ONE night stays are available for last minute bookings, message us! If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled livingroom w/high ceilings, quiet, private bedroom in back, and w/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, and neighbor to some of the BEST restaurants, art and shopping in CT!!!

4.94 out of 5 average rating, 803 reviews

A residential house with a welcoming front porch and manicured bushes is presented. The two-story structure features a light-colored exterior and multiple windows. A narrow driveway to the side leads to a smaller garage. The setting indicates a neighborhood atmosphere.

Apartment in Middletown

Quaint 2br apt- 1 block walk to Wesleyan & Main St

Nicely appointed 1st floor 2 BR apt with mid-century modern inspired decor that is a cozy home away from home. House is 1 block from Wesleyan and 2 blocks from food/fun on Main St, so you don’t need to use your car to visit Wesleyan or get to anything in town since the location is very walkable. Laundry, dishwasher, tv with roku, dvd player and dvd’s, books, bluetooth radio, wifi, front porch and back yard seating, close to Rt 9, I-91, Rt 84, Hartford and short drive to beaches/shoreline/I-95.

4.95 out of 5 average rating, 221 reviews

A striking lake scene captures a vibrant sunset, with vivid hues of red and purple reflected on the calm water. The surrounding shoreline is lined with trees silhouetted against the colorful sky, offering a serene and picturesque view.

Home in East Haddam

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.

4.98 out of 5 average rating, 210 reviews

A red chair is positioned in the corner of a room, surrounded by tall windows that provide ample natural light. The wooden flooring and cozy rug underfoot create a warm setting, while the greenery outside adds a refreshing touch to the view.

Home in Chester

Stunning Artisan Waterfall Escape, Walk Downtown

Rated one of the top 70 airbnb's near NYC on the online mag "Curbed". Featured on EarthxTV "House of What" series. Over 10 years of craftsmanship went into creating a work of art using more than 80% recycled materials. Known locally as "The Recycle House," this is the perfect place to stay to explore shops and galleries in downtown Chester - just steps away. When you are done shopping, come back and relax in the zen-like garden overlooking a waterfall or curl up inside by the fire place.

4.97 out of 5 average rating, 273 reviews

An outdoor space is presented featuring a gravel area surrounded by comfortable blue Adirondack chairs. A fire pit is centrally located, and a wooden deck can be seen in the background, furnished with a dining set and shaded by a bright yellow umbrella.

Cottage in Chester

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.

5 out of 5 average rating, 200 reviews

A young piglet is seen resting on a bed of straw. Its shiny black and white fur contrasts with the golden straw, while its small ears perk up. The background features blurred earthy tones, suggesting a rustic farm environment.

Guesthouse in Portland

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.

5 out of 5 average rating, 126 reviews

Home in Haddam

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!

4.99 out of 5 average rating, 142 reviews

A detailed map indicates three public parking lots and key streets in Downtown Chester. Lot #1 is located on Water Street, Lot #2 at the Cemetery, and Lot #3 on Maple Street. Sidewalks are highlighted for ease of access into the downtown area.

Loft in Chester

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.

4.9 out of 5 average rating, 168 reviews

The image shows a storage cabinet with two shelves containing a variety of dinnerware. Items visible include plates, bowls, glasses, and mugs. The mugs feature various designs, while the plates are stacked neatly in a row. A clean, neutral backdrop enhances the focus on the organized tableware.

Apartment in East Haddam

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.

4.72 out of 5 average rating, 241 reviews

A scenic waterfront gathering is depicted, with guests seated in white chairs facing a wooden deck. A wedding ceremony is in progress, featuring an officiant and wedding party. A lush backdrop of trees and boats on the water create a serene atmosphere.

Cottage in Deep River

Cottage overlooking the CT river

Adorable 1800 cottage with views of the CT River. Upstairs bedroom with a king. Bathroom downstairs with a small tub / shower and a tiny kitchen. Other room is a living room with a desk/ table but has a queen pull out bed ( needs to be requested ahead of time. Watch the Essex steam train, Becky Thatcher riverboat, or hang out at the river, bring your kayaks or paddleboards as there is a boat ramp right across the street.

Guest suite in Wallingford

A lush garden space is surrounded by vibrant greenery and flowering plants. A brick patio features a red umbrella over a small table and chairs, providing a shaded area for relaxation. Decorative planters enhance the tranquil setting, inviting guests to enjoy the outdoors.

5 out of 5 average rating, 591 reviews

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.

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Popular amenities for Haddam vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Haddam

5 out of 5 average rating, 26 reviews

A covered patio area features comfortable outdoor seating framed by lush greenery. A small table is positioned near the seating, creating a cozy space for relaxation. The well-maintained yard extends in the background, offering a serene setting for outdoor enjoyment.

Apartment in Chester

New, modern studio steps from downtown Chester CT

CraigRating, 5 stars5 days ago

Great place! We stayed here on our wedding night and it exceeded our expectations. Quaint, well maintained and beautifully decorated. It was modern, clean with thoughtful attention to detail. Located near the center of Chester, a true hidden gem on the CT river. Friendly hosts.

5 out of 5 average rating, 22 reviews

A charming historic building is depicted, showcasing a shingled facade and a pitched roof. A large tree stands nearby, providing shade over the front porch, which features a white picket fence and neatly trimmed shrubs. An American flag is displayed prominently.

Apartment in Chester

The Little Chestnut.

JeannyRating, 5 stars3 weeks ago

My husband and I just got back from a 4 night stay at The Little Chestnut and it's now added to my Airbnb faves. It's adorable! Communication with Samantha was great- she was super responsive and friendly. Self check in was a breeze with the info provided and the place itself was cozy and welcoming. It sits above a bookstore which I love since I'm an avid reader. The living room area was spacious and the small vintage desk in the corner was perfect for working from my laptop. It was so convenient to have a full kitchen to cook meals in (bring your own spices, food, etc.) as well as a washer & dryer to do laundry before we left. The bathroom is located upstairs where the comfy bedroom is and while tiny (the shower may be cramped for taller people), it was cute and clean. The apartment is also a quick few minutes walk to the quaint main street where all the restaurants,shops,and galleries are (The Village Bistro and Grano Alto for dinner were awesome). I highly recommend staying here!

4.81 out of 5 average rating, 52 reviews

A bright kitchen features white cabinetry and light yellow walls. Equipped with modern appliances including a stove and refrigerator, the space includes a sink and ample counter space. A dining table for three is present, positioned to allow views of the window and living area.

Apartment in Middletown

Cozy Apartment Near Wesleyan and Town Center

RyanRating, 5 stars1 week ago

Great place I felt at home from the moment I stepped inside The place was very very clean and had everything for a long stay. The location was close by to everything

5 out of 5 average rating, 43 reviews

A modern kitchen is presented, featuring white cabinetry and gray countertops. Stainless steel appliances, including a microwave and gas stove, are visible. An inviting layout connects to the living area, with natural light filtering through the doorway in the background.

Apartment in Middletown

Renovated 2-bedroom Near Wesleyan-Middletown

Mary KateRating, 5 stars6 days ago

Great location - close to downtown Middletown and lots of restaurants. Perfect place for us to stay for a family wedding weekend. Was very clean and looked just like the photos. Tim was extremely responsive. We had a great time!

4.95 out of 5 average rating, 38 reviews

A tranquil beach scene captures a curved shoreline meeting calm water, with soft sand and scattered seaweed. The sky is painted in warm hues of orange and purple, reflecting on the surface of the water. Silhouettes of distant rocks and small landmasses are visible on the horizon.

Guesthouse in Clinton

Studio Cottage

KellyRating, 5 starstoday

Looked just like the photos. Private space. Clean and tidy, had a few essentials including coffee! She was very responsive and gave East to follow directions for checking in. Provided great recommendations for nearby places. Location was exactly what we were looking for. Would highly recommend.

4.71 out of 5 average rating, 169 reviews

The exterior of a historic mansion is displayed, featuring a painted mural on one side. Surrounding greenery includes trees and bushes, providing a natural backdrop. The building's windows are visible, reflecting a serene atmosphere in the open lawn area.

Apartment in Higganum

Historic Mansion, Gardens & Meadow

JuliaRating, 5 stars1 month ago

Lots of character and history in this charming and interesting home, in a peaceful setting just around the corner from a great-looking coffee place, several pizzerias, and a reservoir/dam. Beds were comfortable, linens were clean...it might be worth noting that on the first floor there's a wooden door between guest area/resident area of house and upstairs there's just a curtain (and piece of furniture) dividing the two areas.

5 out of 5 average rating, 18 reviews

A spacious outdoor area features a private dock along the lake, with multiple lounge chairs positioned for relaxation. Lush greenery surrounds the well-maintained yard, and a series of steps leads to the cabin. Soft lighting enhances the serene environment at dusk.

Cabin in East Haddam

Lakeshore Cabin with boat dock

IrenaRating, 5 stars3 weeks ago

We spent a long weekend at Dennis’ place and it was nothing short of amazing. Our aim was to relax and enjoy the lake, and we did just that. The house was exactly as described, matched and exceeded our expectations; furnished and the kitchen had everything we needed and more. If we’re back in CT, we won’t hesitate to book the house again! Thanks for being wonderful hosts!