Guesthouse holiday rentals in Connecticut

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Top-rated Guesthouses in Connecticut

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Wilton

4.96 out of 5 average rating, 105 reviews

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 minutes to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is a quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and dishwasher drawer. The bedroom has a queen bed and the living room has a futon couch which folds down. We also have a twin air mattress. It is perfect for one or two people.

Guest favourite

Guesthouse in Southbury

4.93 out of 5 average rating, 295 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Guest favourite

Guesthouse in Stonington

4.98 out of 5 average rating, 243 reviews

True Artist Loft, 5 minutes to downtown Mystic

The Dacha, as it has lovingly been called for almost 80 years was built in 1945 originally as a studio for the artist that resided on the property. The unique structure is truly one of a kind, fully insulated for winter and tucked away from the road, sitting on a quiet piece of land, just 5 minutes to downtown Mystic. Enjoy modern comforts and a designers decor, while settling in front of the fire, or taking a short drive to all that Mystic has to offer- hiking, water, shops and restaurants.

Guest favourite

Guesthouse in Glastonbury

4.94 out of 5 average rating, 139 reviews

Unique luxurious private building in historic area

Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.

Guest favourite

Guesthouse in Norwalk

5 out of 5 average rating, 126 reviews

Private one bedroom cottage on Conn. seashore

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian friendly town; you don't even need a car while here.

Guest favourite

Guesthouse in Portland

4.99 out of 5 average rating, 130 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.

Guest favourite

Guesthouse in Killingly

4.98 out of 5 average rating, 129 reviews

The Carriage House at Chaprae Hall

Welcome to the Carriage House at Chaprae Hall! A cozy, quiet respite from a busy world awaits you. This fully furnished & appointed vintage living space has been updated over the years to be an inviting and welcoming stop for your journey. Whether you’re traveling for business, in town for an event, or looking for a central home base for day trips across southern New England, we've got you covered with your own kitchen, full bath, living space, and bedroom with a queen-sized bed.

Guest favourite

Guesthouse in New Haven

4.94 out of 5 average rating, 267 reviews

Square 6ix

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.

Guest favourite

Guesthouse in Mystic

4.99 out of 5 average rating, 576 reviews

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Guest favourite

Guesthouse in Glastonbury

4.92 out of 5 average rating, 190 reviews

Charming Barn Apartment

Our one bedroom apartment in a colonial barn has a country feeling but is a 10 minute drive into downtown Hartford, and halfway between Boston and New York City .There are woods on one side and from the living area look out on a hillside where you can sit for a spell or spend some time on the private stone patio right outside the door. There are beaches and casinos within an hours drive.

Guest favourite

Guesthouse in Granby

4.99 out of 5 average rating, 745 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Guest favourite

Guesthouse in Guilford

4.99 out of 5 average rating, 470 reviews

Get Back to Nature at a Modern Wood Clad Getaway

SUMMER IS HERE. The beaches are open. Beautiful days and nights. Hike on the trails. Bike along the ocean. Cardinals, blue jays, bluebirds, gold finches and more. Great places to shop and eat or just relax in our cozy guest house. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.