Last Updated January 13, 2021 1/13/2021

17 Charming Airbnbs in Connecticut

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Whether you’re looking for a quaint retreat, an outdoorsy getaway, or small-town charm, chances are that you can find it in Connecticut. As an alternative to choosing a familiar hotel chain for your trip, you can opt for a local Airbnb to get to know the community a bit better and feel right at home. Here are our top picks for Airbnbs in Connecticut.

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Windy Top Cottage - Granby Windy Top Cottage
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Windy Top Cottage

Windy Top Cottage - Granby

This very popular guesthouse accommodates up to four people and is an old stone cottage constructed in 1932. It’s a place to come to for fresh country air and charming 1,000-square-foot space with original bath fixtures. There is no kitchen here but the great room has a vintage fridge and a small coffee service area. The hosts also provide a toaster oven and espresso machine. The second floor has the bedrooms, and the cottage also has an exterior patio and firepit for making s’mores. When you stay here, you’ll be near the best boarding schools in the state – seven of which are all within 20 miles of the cottage.

Cozy, Modern Forest Cabin with Babbling Brook - Cornwall Cozy, Modern Forest Cabin with Babbling Brook
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Cozy, Modern Forest Cabin with Babbling Brook

Cozy, Modern Forest Cabin with Babbling Brook - Cornwall

This entire house is available to rent on Airbnb for up to four people and has two bedrooms and two baths. It’s a cozy cabin from the 1930s with a modern interior, new kitchen, and that overlooks a forested hill and private brook. Within 10 minutes, you can get to great restaurants, skiing, swimming, and kayaking. The Appalachian Trail is also close by for hiking. Guests who stay here have access to a deck with outdoor seating, high-speed Wi-Fi, and Netflix. Sleeping accommodations are two queen-size beds in their own bedrooms.

Waterfront Studio Apartment with Fireplace - Milford Waterfront Studio Apartment with Fireplace
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Waterfront Studio Apartment with Fireplace

Waterfront Studio Apartment with Fireplace - Milford

Guests also love this apartment for two people because it’s off the patio level of a waterfront home. You’ll get lovely views of Long Island Sound and have your own entrance. It’s close to the Metro North railroad and I-95. Other perks of staying here are the 50-inch smart TV, Wi-Fi, cable TV, and gas BBQ grill. There is not a full-size stove in the space, but you will have a toaster oven, blender, coffeemaker, induction cooktop, and oven. Although the studio apartment isn’t on a beach, you’ll have access to the shoreline for walks along the water.

Tiny House on a Sustainable Farm - Guilford Exterior of Tiny House on a Sustainable Farm
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Exterior of Tiny House on a Sustainable Farm

Tiny House on a Sustainable Farm - Guilford

Two guests can stay in this tiny house on the Waystone Farm and enjoy the lovely eight acres here. The farm has goats and chickens and is where the hosts grow their own food. When you’re here, you can kayak, hike, go to the beach, learn to can vegetables, and help out on the farm if you like. Inside the tiny house, you’ll get a full bath, full kitchen, Wi-Fi, air conditioning, heat, and a queen-sized bed for sleeping. It’s a great place to get away from your normal routine; however, pets are not allowed in the tiny house.

Unique Coastal Chalet - East Lyme Unique Coastal Chalet
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Unique Coastal Chalet

Unique Coastal Chalet - East Lyme

You can have this entire chalet to yourself and up to four total guests when you book on Airbnb. It’s located in a private beach community and less than a mile from the private beach. The space is 830 square feet in size and has free Wi-Fi. From here, you can get to Niantic Village in three miles, Essex in 12 miles, and Mystic in 20 miles. For outdoor living, there’s a sunny front deck, fire pit in the backyard, and playground with basketball and tennis courts in the beach community.

Water Forest Retreat, Hikers Haven - Norwich Water view at Hikers Haven
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Water view at Hikers Haven

Water Forest Retreat, Hikers Haven - Norwich

For a tiny house option, this retreat is on the same property as the Norwich octagon house and treehouse listed above. It is about 2/10ths of a mile downhill through a forest to access and has 57 steps, so pack light. The tiny house is 198 square feet in size and has heat but no running water. There’s a bathroom in the house with a vented composting toilet. In lieu of a full kitchen, there are camp-style cooking supplies provided. The private outdoor shower is at the main house and about a four-minute walk away.

The Tree House at Underhill Hollow - Thompson View of the Tree House at Underhill Hollow
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View of the Tree House at Underhill Hollow

The Tree House at Underhill Hollow - Thompson

For a unique stay in Connecticut, book this treehouse for up to four people. It’s great for both family vacations and romantic getaways, and it’s situated on a seven-acre 1825 farm. The adventurous property has chickens, deer, blue heron, a hammock, and walking paths. You’ll feel like you’re camping but have a real bed, internet, and air conditioning. The treehouse has a composting toilet, and guests can also use the flush toilet in the main house. There’s an outdoor hot water shower, a mini-fridge and electric grill in a small cooking area, and many restaurants in the area. Plan to bring your own towels, linens, blankets, and pillows if possible.

Bluebird Farm Barn Loft - Willington Bluebird Farm Barn Loft
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Bluebird Farm Barn Loft

Bluebird Farm Barn Loft - Willington

For a unique farm stay experience in Connecticut, book this Airbnb that’s a converted loft and garden gazebo on Bluebird Farm. It’s a 40-acre sanctuary on a working farm that has a kitchenette, bathroom, and shower. Guests have access to the gas grills, animal pasture when guided by the host, and lots of farm experiences all around. Pets and parties are not allowed here. Up to 15 people can stay here but there is an additional charge per person after the first guest. An outdoor porta-potty rental is required for groups of eight people or more.

Cozy Lake Cottage, 10 Minutes to Mystic - Ledyard Water view at Quiet & Cozy Lake Cottage, 10 minutes to Mystic
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Water view at Quiet & Cozy Lake Cottage, 10 minutes to Mystic

Cozy Lake Cottage, 10 Minutes to Mystic - Ledyard

Meanwhile, this cottage is a wonderful Airbnb property to stay in when you visit the Connecticut communities of Ledyard and Mystic. Up to four guests can stay here in the two-bedroom, one-bath cottage by the lake. Families, couples, and groups of friends enjoy the hot tub, kayaks, fire pits, and games provided. The cabin has a rustic feel and is right on the water with a screened-in porch for enjoying meals with a view. The hot tub overlooks the water, and there’s a massage therapist here that you can schedule a massage with.

Water Forest Retreat Tree House - Norwich View of Water Forest Retreat Tree House
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View of Water Forest Retreat Tree House

Water Forest Retreat Tree House - Norwich

This couple in Norwich has several highly recommended and unique Airbnb properties that will make your stay in Connecticut very special. One Airbnb rental, this treehouse, accommodates two guests in 168 square feet of space and is nestled in 100 acres of forest. It has electricity but no running water. The treehouse has a composting toilet, queen-size bed, and a cabinet with camping essentials for preparing camp-style meals. There is no traditional kitchen here. You’ll love the 2.5 miles of trails and guided nature walks with your host. Stay here for your next glamping adventure!

Private Room in Historic Home, Close to Yale - New Haven Yard view - Private Room in Historic Home, Close to Yale
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Yard view - Private Room in Historic Home, Close to Yale

Private Room in Historic Home, Close to Yale - New Haven

Another option is to book this apartment in a historic home in New Haven and be less than 10 minutes from downtown. Yale Fields and Hopkins School are within walking distance when you stay at this 1916-built charming home. Guests who stay herein this completely private third-floor apartment get a queen-size bed, private bath, shared bath, shared kitchen and dining area, and Wi-Fi. Many traveling nurses at Yale University Hospital stay here, as well as students and professionals. You’ll have your own mini-fridge and microwave in the apartment’s living room for quick meals and also have access to the home’s full kitchen, library, living room, and solarium as shared spaces.

Water Forest Retreat Octagon - Norwich View of Water Forest Retreat Octagon
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View of Water Forest Retreat Octagon

Water Forest Retreat Octagon - Norwich

This unique octagonal tiny house that’s 144 square feet in size sits on 100 acres of forest land. It’s an ideal place to relax, snowshoe, make art, gaze at the stars, write, and watch the wild animals. The octagon house has electricity but no running water. Enjoy the hiking trails, try your luck with some catch-and-release fishing, and head over to Gardner Lake State Park about 15 minutes away. The octagon house has a composting toilet, and the outhouse has an electric heater for the winter months.

Cottage at Furnace Brook - Cornwall Exterior of Cottage at Furnace Brook
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Exterior of Cottage at Furnace Brook

Cottage at Furnace Brook - Cornwall

Travelers in Connecticut also love this guesthouse that’s a semi-detached cottage in the Litchfield Hills. It’s cozy, clean, and newly renovated. The Housatonic River is close by, and there’s a large porch that’s great for relaxing on. Artists and writers love it here. The space has a double-size bed for guests to sleep in. You can get out to explore the restaurants, galleries and day hikes from here because the cute small town of Kent is just eight miles away. You can also check out Mohawk Ski Area and Metro-North from here.

Summer Hill Farm Apartment - Brooklyn Seating area at Summer Hill Farm Apartment
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Seating area at Summer Hill Farm Apartment

Summer Hill Farm Apartment - Brooklyn

This apartment accommodates up to five guests and is in a quiet area with a wooded trail, private pond, and serene pasture. It’s near numerous schools, wedding venues, the CT Wine Trail, and New England events. You’ll be in a two-unit converted barn home with original features like cathedral ceilings and natural wood beams. Perks of staying here are the outdoor dining area, walking trails, friendly goats living onsite, country views, and shops and restaurants nearby if you want to venture out.

Guilford Home in the Woods - Guilford Windows at Guilford Home in the Woods
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Windows at Guilford Home in the Woods

Guilford Home in the Woods - Guilford

Here’s a highly rated guest suite for one or two people that is on the edge of Long Island Sound. It has 39 miles of trails near the house and a boatyard down the hill. The property is also about 18 minutes from New Haven and the Yale campus, and the Guilford train station is a short drive away with trains to New York City. You’ll be in a ground-floor apartment that overlooks a forest scene atop a hill. Since it is a separate space, you’ll have plenty of privacy and access the space through a door next to the garage.

Lakeside Cabin on Beach Pond with Sauna - Voluntown Lakeside Cabin on Beach Pond with Sauna
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Lakeside Cabin on Beach Pond with Sauna

Lakeside Cabin on Beach Pond with Sauna - Voluntown

It’s also fun to rent a cabin in Connecticut for your getaway. This one has three bedrooms and one bath, and it is a camp cottage built in the 1960s. It has two bedrooms and sleeps four people, while there’s also a detached bunkhouse with three single beds if your group is larger. From here, you are within walking distance to trails and get to enjoy a peaceful lakeside location. The sauna is available year-round, the cabin has propane and electric heat, and the cabin has everything you need to cook meals.

Private Room in Cheshire Home - Cheshire Bedroom at Private Room in Cheshire Home
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Bedroom at Private Room in Cheshire Home

Private Room in Cheshire Home - Cheshire

Dog lovers enjoy staying in this private room in a house in Cheshire. One or two guests can stay in the room and bring dogs for $10 per dog per night. Dog sitting can be arranged also for an additional cost. There are four sweet labs that live in the home. The home is near parks and hiking, and it has a fenced backyard. The shared bathroom and kitchen are available for guests to use, and the bedroom has a double-size bed. If you stay for a week or more, you can use the home’s laundry facilities.

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