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Top 13 Vacation Rentals in Connecticut

Connecticut may be one of the smallest U.S. states, but it packs a lot into its corners. This popular vacation spot is famed for its peaceful beaches, stunning lakes, verdant countryside views, and fascinating history. You’ll find plenty to do while you’re here,  whether you’re checking into a rental overlooking the water or heading deep into the forest for a few days of tranquility. Not sure where to stay during your trip to Connecticut? Read on for all of the top vacation rentals spanning each corner of this state.

Cozy Direct Waterfront Airbnb - East Haven Cozy Beachhut - Direct Waterfront
Credit: Cozy Beachhut - Direct Waterfront by Airbnb.com

Cozy Direct Waterfront Airbnb - East Haven

If your dream vacation involves a lot of time on the beach or in the water, you’ll definitely fall in love with this cozy beachfront getaway. With direct waterfront access, you’ll be able to enjoy your morning coffee sitting on the deck overlooking the waves and, once you’ve sufficiently woken up, can head right down and dip your toe or throw yourself into the water without hesitation. A four-bedroom house with space for up to eight guests, this picturesque spot features large bedrooms, charming bathrooms, a new kitchen, a very large deck, and all the other amenities you could ask for. Wake and fall asleep to the peaceful sound of ocean waves and look out of each room to admire those expansive views of the Long Island Sound. Feeling hungry? There are two incredible seafood restaurants within easy reach of this Airbnb, too.

The Cove Cabin The Cove Cabin
Credit: The Cove Cabin by Airbnb.com

The Cove Cabin

The Cove Cabin is one of the most popular vacation rentals in Connecticut and it’s easy to understand why. Hidden deep in the forests of Sherman, this unique spot is truly a one-of-a-kind adventure and is best suited to those looking for a more rustic experience. Well, that’s what you’ll think from the outside. But step inside The Cove Cabin to admire its pristine decor, featuring shiny wooden surfaces, colorful rugs, impressive artwork and soft lighting. It’s the very definition of an Instagram-worthy experience and it’s somewhere you’ll instantly feel at home. Despite its characterful exterior, the house has been updated to offer all modern comforts. It features a large fireplace in the living room, a porch overlooking the lake, central heating and air conditioning depending on the weather outside and a fully equipped cook’s kitchen.

Red House on the Knoll in Indian Cove - Guilford
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Red House on the Knoll in Indian Cove - Guilford

This cozy red house may look a little small from the outside but step through its front doors and you’ll be surprised by just how spacious it is. With high-arched beams and a traditional yet modern theme throughout, this three-bedroom Airbnb is a wonderful vacation spot for anyone heading to Guilford. Get lost in the woods and escape to the ocean at this spacious cottage, with its newly renovated 1920s design and wooden floors, high ceilings, and stone fireplaces. A great house for family gatherings or reunions, it’s made up of a master bedroom and two slightly smaller ones. The outdoor patio offers a great place to enjoy dinner each evening, and there’s a fire pit located in the yard if you’re looking to go all out and toast some marshmallows. Over in the garage, you’ll find bikes and kayaks.

The Candlewood House - Litchfield The Candlewood House
Credit: The Candlewood House by Airbnb.com

The Candlewood House - Litchfield

This incredible themed house offers plenty of natural light throughout its wooden, cabin-like structure. It’s a place you’ll wake up every morning ready to go and explore as the sunlight soaks through the wooden beams and into each of its five bedrooms. This large vacation rental is designed for all kinds of travelers, with room for up to 11 guests in total and many communal spaces to enjoy together. A beautiful modern geothermal home, it sits on 3.8 acres of park-like land and is located in Litchfield County close to Candlewood Lake. Although it’s situated in a very quiet neighborhood, the house is only minutes away from shops, restaurants, a Starbucks, farms, and supermarkets, so you’ll have everything you need nicely close by. A great spot for families, the room themes here include a Japanese-style washitsu room, an American Vintage room, an African Safari room with giraffes, and a Disney Mickey Mouse room.

Heavenly Treehouse in Countryside with Farm Animals - Willington Heavenly Treehouse in Countryside
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Heavenly Treehouse in Countryside with Farm Animals - Willington

There’s space for up to four guests at this beautiful treehouse, but it’s just as suitable for a couple looking for a romantic getaway in Connecticut together. A wonderful place in the middle of a farm, it’s a one-of-a-kind stay that offers all kinds of home comforts. This amazing cabin in the sky has all the modern amenities you’ll need to relax in the countryside while still giving you a sense of camping. Spacious but simply designed for your comfort, it features a kitchenette, bathroom, and shower, as well as a cozy bedroom with stunning views that you’ll enjoy every morning. Walk the grounds and even take a small hike, say hi to the farm animals who call this place home, or relax among the farm’s grounds to soak up the atmosphere.

Lakefront house 10 Minutes to UConn - Coventry Lakefront house 10 min to Uconn
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Lakefront house 10 Minutes to UConn - Coventry

Over in Coventry, you’ll find this three-bedroom lakehouse. A great midpoint for anyone looking to be close to nature but also within easy distance of shops, restaurants and more, this beautiful house offers plenty for all kinds of guests. The house is located directly in front of the sandbar and goes by the name Panorama for the panoramic views it has of Coventry Lake. Wander through to the large kitchen to be met with vaulted ceilings and wood beams or check out the main living space with its two large sliding glass doors which look out to the lake. The house has a Nespresso machine with free pods included, so you’ll probably spend most mornings here enjoying a cup of coffee while admiring the views. Outside, there’s a deck box with sand toys, some beach chairs, floats, and a floating raft to jump off of.

The Little Lake Cabin with Hot Tub & Fire Pit - New Fairfield The Little Lake Cabin with hot tub & fire pit
Credit: The Little Lake Cabin with hot tub & fire pit by Airbnb.com

The Little Lake Cabin with Hot Tub & Fire Pit - New Fairfield

This two-bedroom cabin is truly a one-of-a-kind one, allowing you to escape into the peaceful woodlands for a few days of laidback living. With its own hot tub and fire pit, you’ve got everything you need for relaxation and entertainment, no matter which time of year you’re visiting. There’s space for four guests at this spot, making it perfect for a small group of friends looking to escape together for a few days. The perfect place to soak in the magic of nature by relaxing, hiking, and enjoying the lake, this cabin was named one of the best Airbnbs in the area and is well located for all kinds of adventures. Spend your days on the lake, exploring nearby towns, wineries, and antique shops and then spend the nights in the hot tub, by the fire pit roasting s’mores and gazing up at the stars.

Hilltop Retreat- Lakefront with Dock - New Fairfield Hilltop Retreat- Lakefront with Dock
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Hilltop Retreat- Lakefront with Dock - New Fairfield

This hilltop vacation retreat allows you to enjoy all that Candlewood Lake and Squantz Pond State Park have to offer, set in a scenic spot with lakefront access for even more enjoyment. With two bedrooms and space for up to six people, it’s designed for a family or group of friends looking to spend some time in New Fairfield. This waterfront property is suitable for both winter and summer getaways and features a private dock and stunning views from almost every room in the home. There’s plenty of indoor and outdoor entertaining space and a wood-burning fireplace to keep you toasty during those evenings when it does get a little chilly. On warmer days, you’ll love the egg-shaped chairs and balmy weather and, when it’s properly warm, you’ve even got free access to the property’s kayaks.

"The Palms" Direct Waterfront Vacation Home - Milford
Credit: "The Palms" Direct Waterfront Vacation Home by airbnb.com

"The Palms" Direct Waterfront Vacation Home - Milford

There are vacation homes and then there are Vacation Homes and this one deserves a little extra capitalisation for sure. A five bedroom house with space for up to 12 guests, it’s well equipped for all kinds of adventures and promises to set the scene for a seriously memorable getaway. With neon lights and direct waterfront access, it’s hard not to get a little excited as soon as you’ve got the keys to this place. Inside, you’ll find an open plan living and dining room with stylish modern coastal decor and all the amenities needed. There’s a large kitchen designed to make cooking up a feast a breeze, and plenty of outdoor space to soak up the sunshine. Exteriors include an oversized patio uniquely decorated with palm trees and, of course, those gorgeous views of the water just beyond.

Bucolic Bliss in 1790s Farmhouse - Litchfield Bucolic Bliss in 1790s Farmhouse
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Bucolic Bliss in 1790s Farmhouse - Litchfield

This historic five-bedroom house was built in 1793 and renovated early in the 21st century, making it a brilliant fusion of the old and the new. A picturesque spot with gorgeous views from almost every room, it’s a perfect vacation spot for you and your family or anyone looking to spend some quality time with nature. There’s space for up to eight guests at this spot, with unique 18th-century details like wide-timbered wood floors, exposed beams, and tiny nooks in every direction. Wander through the grounds to admire the scenic countryside views all around, or take a stroll throughout the house to admire its impressive decor. The common spaces here include a dining room, family room, open kitchen, and living room area with a functional fireplace, an enclosed porch, a home studio, and a large patio for those balmy evenings during golden hour.

Luxurious Barn With New England Charm - Fairfield Luxurious Barn With New England Charm
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Luxurious Barn With New England Charm - Fairfield

This impressive barn offers a heavy dose of New England Charm and once you’ve checked in here, you’ll always fondly remember it as a vacation home of dreams. Luxurious both inside and out, it’s one of the most prestigious spots in the area with a huge, sweeping design that captivates anyone who spots it from afar. Its three decades of tasteful renovations, many of which used repurposed material, have definitely rendered this converted barn into something magazine-worthy. Set back from the road on a one-acre patch of wooded land with a babbling brook just nearby, it’s home to 30-foot ceilings, exposed wooden beams, dozens of windows, an array of eclectic furniture, and even a grand piano. The house was designed for a varied group of travelers, which means you’ll find a mixture of king and queen-size beds as well as twin beds throughout its four bedrooms.

The Cottage at Madison & Meadow Farm - Washington The Cottage at Madison & Meadow Farm
Credit: The Cottage at Madison & Meadow Farm by Airbnb.com

The Cottage at Madison & Meadow Farm - Washington

The word “cottage” doesn’t really do this vacation rental justice, as its huge size would probably have you replacing that word with something like “mansion” or “dream home that I long to return to again and again.” With two bedrooms and space for up to four guests, it’s an awe-inspiring spot for families or even a couple who want a bit of extra space to enjoy. With wooden beams and high ceilings, it’s every inch a historical Airbnb, complete with gorgeous views of the surrounding farm and a general air of tranquility all around. Located in the charming town of Washington, this beautiful country cottage provides a peaceful, enjoyable opportunity to relax and wind down. While you’re here, make the most of the famed outdoor activities, like hiking, fishing, skiing, bird watching, and stargazing. Three of Litchfield County’s best skiing and snowboarding resorts are only 30 minutes away if you’re looking for a little more fast-paced action.

Stunning Lakehouse on 4 Acres with Hot Tub Stunning lakehouse on 4 acres with hot tub
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Stunning Lakehouse on 4 Acres with Hot Tub

Head to Woodstock, Connecticut for a lakehouse adventure that you’ll reminisce over for years to come. This incredible property is sat on four acres of land with direct access to the lake itself. A place where you’ll probably spend most of your time outside, it’s home to not only that incredible body of water but also its very own hot tub. There’s room for up to 10 guests at this vacation rental, making it a great place for you and a large group of friends to catch up while enjoying the very best of Mother Nature’s offerings. Known for its bass fishing and beautiful birds, this lake is wonderful for swimming, kayaking, and reveling in nature. The 20 foot cathedral ceilings, floor-to-ceiling picture window, central air conditioning, stunning kitchen, and designer furnishings make this one of the most memorable Airbnbs around.

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