Vacation rentals in Haddam

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Top-rated vacation rentals in Haddam

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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

4.78 out of 5 average rating, 288 reviews

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.

Top guest favorite

A tranquil lakeside scene is captured, featuring a sandy shore beside Cedar Lake. Two benches are positioned near the water, with towels draped over them. Sunlight filters through nearby trees, creating a serene atmosphere. The calm water reflects the surrounding greenery.

Apartment in Chester

4.98 out of 5 average rating, 177 reviews

Charming Chester Retreat - Cottage

Come soak up the last of summer! 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

Guest favorite

The exterior of Lori Warner Studio/Gallery showcases a vibrant red door framed by large glass windows. A deep blue awning offers shade, while decorative planters with greenery are positioned beside the entrance. Outdoor seating is visible in the background, complementing the inviting atmosphere.

Apartment in Chester

4.93 out of 5 average rating, 387 reviews

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

ONE night stays are available for last minute bookings, please message us. Our lovely, well designed place is 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!

Top guest favorite

A charming cottage features wood shingle siding and a neatly arranged entrance. The front yard showcases a manicured area with green grass, accompanied by a duck and a chicken. Nearby, expansive fields and a rustic barn complete the serene rural landscape.

Guesthouse in Portland

5 out of 5 average rating, 234 reviews

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.

Top guest favorite

An open-concept living space features light-colored wood flooring and a cozy seating area with a white couch and wooden coffee table. A small dining table is positioned nearby, while a stylish staircase leads to an upper level. A television is mounted on the wall, adding to the modern atmosphere.

Home in Haddam

5 out of 5 average rating, 132 reviews

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!

Top guest favorite

A comfortable living area is presented with a gray sectional sofa and a wooden coffee table resting on a colorful area rug. Natural light enters through large windows, illuminating the hardwood floors and revealing a small antique chest and a decorative lamp.

Apartment in Deep River

4.93 out of 5 average rating, 150 reviews

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.

Top guest favorite

A charming exterior view showcases the entryway to The Village Loft, featuring a decorative sign that identifies the loft. Soft lighting from a hanging lamp creates an inviting atmosphere along the quaint facade above The Village Bistro.

Loft in Chester

4.99 out of 5 average rating, 150 reviews

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.

Guest favorite

The exterior of a single-story apartment features a beige facade with brown trim. A welcoming front door is flanked by potted plants, and a covered porch is visible. Natural light illuminates the surroundings from a clear blue sky.

Apartment in East Haddam

4.89 out of 5 average rating, 178 reviews

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.

Top guest favorite

A round wooden table is set with woven placemats, featuring a white cup filled with frothy coffee. A tall vase with a vibrant sunflower adds a touch of color, while a small tray with assorted snacks is visible in the background.

Apartment in New Britain

4.96 out of 5 average rating, 207 reviews

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Top guest favorite

An elegant Arts & Crafts bungalow showcases a blend of architectural styles under a clear blue sky. The inviting façade features a distinctive porch, a brick chimney, and a nearby garage. Lush gardens adorned with vibrant plants enhance the home’s outdoor appeal.

Guest suite in Wallingford

5 out of 5 average rating, 610 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.

Top guest favorite

The living room features a large Smart TV above a fireplace, complemented by a cozy area rug. Various seating options include a white leather sofa and two reclining chairs. Sunlight filters through sheer curtains, enhancing the inviting ambiance of the space.

Home in Middletown

5 out of 5 average rating, 101 reviews

Family Stays, CT

Centrally Located Cozy Family Vacation Home: Just 1.2 miles from Wesleyan University, our welcoming home is an ideal choice for families, solo travelers, couples, professionals, business travelers, and almost anyone. Whether you're here to explore Middletown or the surrounding Connecticut towns, you'll have the entire property to yourself for a comfortable and enjoyable stay.

Guest favorite

Two paddleboats are moored next to a wooden dock, resting on calm waters. The boats feature a blue color with a simple design, and the dock extends towards the lake, reflecting the peaceful setting.

Apartment in Middletown

4.83 out of 5 average rating, 174 reviews

Lakeside apartment 2.5 miles from Wesleyan campus!

Walk out to your private deck from either the living room or the kitchen. Newly-refurbished apartment in a beautiful, peaceful setting on small lake, suitable for swimming or fishing. Enjoy free use of our paddleboat! This is an in-law apartment attached to our home, so we will be nearby to help with any issues that may arise during your stay.