Guesthouse vacation rentals in Connecticut

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Popular amenities for Connecticut guesthouse rentals

Family-friendly guest house rentals

Guest favorite
A serene outdoor space features four grey Adirondack chairs arranged around a small table, set on a lush green lawn. Surrounding foliage adds a touch of nature, while a clear sky provides a bright backdrop.
Guesthouse in New London
4.97 out of 5 average rating, 107 reviews

Fully Renovated, Ocean Views, Fireplace & Beach

EvaRating, 5 stars4 weeks ago
Dawn’s place is private, well-appointed and in a fantastic location. You have an ocean view from the cottage, have access to a small semi-private beach, and a brief walk along the coast via the gorgeous neighborhood takes you to the larger Ocean Beach & boardwalk. Additionally there are very good restaurants, state parks, museums and pubs nearby. You’ll feel pampered by Dawn’s consideration and attention to detail and refreshed by the location and beaches.
Guest favorite
Guesthouse in Norwalk
5 out of 5 average rating, 69 reviews

Cottage by the Sea

Agni MaRating, 5 stars2 months ago
We came for a quiet beautiful space to retreat too while visiting family during a very busy time. And being at Esme’s was so amazing … quiet,comfortable, great view Ty !!!
Guest favorite
A fisherman is seen casting a line across the tranquil Farmington River, surrounded by lush greenery and mist rising from the water. Towering trees provide a natural frame, creating a serene outdoor setting.
Guesthouse in Barkhamsted
4.89 out of 5 average rating, 98 reviews

Farmington River Carriage House Pleasant Valley CT

WilliamRating, 5 stars6 days ago
Great stay! Lots of wildlife on the river. Will definitely come back.
Guest favorite
A tranquil section of the Little River is depicted, featuring cascading water creating gentle ripples. Sunlight reflects off the surface, enhancing its natural beauty. Lush green leaves frame the scene, adding a touch of nature to the flowing water.
Guesthouse in Sprague
4.96 out of 5 average rating, 201 reviews

House on Little River / Writer Retreat

PamelaRating, 5 stars8 months ago
Cabin on Little River met our expectations and more. Myself, 2 sisters and my daughter wanted a quiet getaway. A charming open concept post and beam, pine floors and wood trim, woodstove for winter, deck with charcoal grill. It's very rural and IN the woods ( so bring bug repellant). Even though the host's home is visible you still feel tucked away. Kitchen and bath are modern and clean and the beds and livingroom were very comfortable. The soothing sound of the river is always present. It was relaxing to sit down in the adirondack chairs near its bank. The woods provide a place to walk. Lake is across the road. Glenn informed us of several events nearby that we were really interested in...but we never felt like leaving the cabin! There's a big firepit nearby and wood provided. Glenn is a wonderful host. A fellow artist, I asked to see his studio on the ground level. Even bought a couple small paintings. Do not hesitate to book this place if you are looking for a quiet respite!
Superhost
A well-maintained grass area leads to a fenced saltwater pool, surrounded by colorful trees displaying autumn foliage. The pool house features a charming design, positioned adjacent to the pool, while a stone pathway guides visitors through the scenic landscape.
Guesthouse in Glastonbury
4.77 out of 5 average rating, 96 reviews

59 Old Maids Lane pool house

LinnaeRating, 5 stars5 months ago
We enjoyed the coziness of the pool house during our Thanksgiving stay. The location was close to our family and friends. It was private and quiet. Alice responded promptly to our questions. We would like to return when the weather is warmer to take advantage of the pool and the outside surroundings. The Goulds
Guest favorite
A two-story barn-style building is set in a lush green landscape, featuring light-colored siding and a dark roof. Red doors provide a contrasting detail. Surrounding greenery and a large rock formation accentuate the rural tranquility of the property.
Guesthouse in Granby
4.89 out of 5 average rating, 233 reviews

The Loft @ Lost Acres ~ A Peaceful Rural Escape!

AlisonRating, 5 stars3 weeks ago
Really appreciated Ken's thoroughness and thoughfulness before we arrived, and availability if we needed anything while we were there. The apartment is cozy and comfortable, and the area has lots of possibilities for exploration. Really appreciated the guidebook assembled for guests. Comfy beds, lots of towels, warm and efficient heat.
Superhost
A charming brick house is framed by lush greenery and vibrant blue hydrangeas. A white picket fence borders the garden, and the front porch features decorative columns, enhancing the welcoming facade of the property.
Private room in New Haven
4.82 out of 5 average rating, 204 reviews

Amadeus "English Garden Studio"

SanaeRating, 5 stars4 days ago
I loved the house with skylights very much. On top of beautifully decorated interior, there were many thoughtful amenities that made longer stays very comfortable. I’d love to come back. Thanks!
The exterior of the two-story cottage is framed by lush greenery, featuring a welcoming porch with white columns. Large windows allow natural light to flood the interior. The gentle slope of the roof and classic shutters enhance the charming architecture, while a hint of red barn peeks in the background.
Guesthouse in Norwalk
5 out of 5 average rating, 21 reviews

Guest Cottage in Rowayton

Alfonso JamesRating, 5 stars9 months ago
Mary was very helpful. She checked in with us to see if we needed anything for our stay and provided great guidance on where to go for the fireworks on the 4th of July, where entertainment were going on in the town, restaurants and shops. She acted as our own concierge.

Guest house rentals with a patio

Top guest favorite
A private guest house is framed by lush greenery, with a gently sloping wooden ramp leading to the entrance. The exterior features a simple design harmonizing with its woodland surroundings, while tall trees and ferns create a peaceful atmosphere.
Guesthouse in New Milford
5 out of 5 average rating, 30 reviews

House in the Trees w/ Pool & Tennis

SashiaRating, 5 stars1 month ago
Julia was an absolute pleasure. I required some special accommodations which we had discussed prior to my visit, and she was amazing about it. The property is stunning. I would 100% recommended Julia’s place, and wouldn’t hesitate to return.
Guest favorite
A scenic view of a calm waterway is framed by a wooden deck. Two white chairs with blue stripes are positioned for relaxation. A small table holds decorative items, while a dock extends into the water, surrounded by greenery and gentle waves.
Guesthouse in Fairfield
4.93 out of 5 average rating, 15 reviews

The Creekside Cottage

AndreRating, 5 stars2 months ago
Beautiful stay! Came to CT with 2 winterstorms back to back and below freezing temps. The place was cozy and warm the whole time! A great place to relax and watch the tide come in and out. And the "throne" room has a great view!
Top guest favorite
The cottage blends into the natural landscape, framed by vibrant fall foliage. The structure features large windows and a gable roof, while greenery surrounds the entrance, creating an inviting view of the serene outdoor environment.
Guesthouse in Pomfret
5 out of 5 average rating, 46 reviews

Cottage in Quiet Corner. Four miles from town.

NathanRating, 5 stars1 week ago
We loved our stay with Gary and Cindy! Cindy met us and showed us around. She kindly offered books for our kids and showed us her beautiful plants. They have lots of grandkids so they were happy to let our kids run free in their yard with their dogs, which my kids loved. The kids loved the little cubby hole beds and the cottage was comfortable and cozy. Cindy even had muffins and flowers awaiting us in the cottage. Highly recommend!
Top guest favorite
A serene outdoor space features comfortable seating arrangements overlooking a flowing brook, framed by lush greenery. A fire pit and a rustic outdoor heater add charm, while the sound of the nearby waterfall enhances the tranquil environment.
Guesthouse in Sharon
4.94 out of 5 average rating, 107 reviews

Cottage with a Waterfall View

JeffreyRating, 5 stars1 week ago
The cottage is beautiful and such a surprise when you open the front door - the magical stream is right out the window. Although the cottage is close to the road you would never know it - the back patio is just perfect!! An easy drive to a a number of small and lovely quintessentially New England villages. We would highly recommend Jeff and Elizabeth's cottage!
Guest favorite
A cozy living area is featured with a comfortable sofa adorned with colorful cushions. Light floods in through a large window, highlighting the warm wooden floors and exposed beams. A small coffee table sits in the center, while a vintage cabinet and bar stools complete the inviting space.
Guesthouse in Madison
4.97 out of 5 average rating, 100 reviews

Chic Coastal Escape - 5 Mins to the Beach

MelissaRating, 5 stars1 week ago
Kelly was a very considerate, warm, and communicative hostess. The location was amazing with close proximity to Surf Club Beach, playground, Soccer, and baseball fields and adorable CT Shoreline towns. We also spent time at Jacob’s beach in the next town over called Guilford, land Essex which is just 15-20 minutes away. A few minutes by car are the Madison Beach Hotel and Christie’s restaurant. One of the best attributes for my family was the spacious backyard completely outfitted for children. The carriage house apartment, over the garage, is loft-like, very bright, and decorated sophistically. From street level, there are about 15 steps up to the open floor concept sitting area, bistro table, and kitchenette that lead to an en suite bedroom and bath plus a spacious deck off of the bedroom. My twins loved the plush bed! Thank you for such an enjoyable stay!
Guest favorite
Guesthouse in Weston
5 out of 5 average rating, 66 reviews

Adorable 1-Bedroom Cottage w/ Mezzanine Weston, CT

TamaraRating, 5 stars3 months ago
Jacques was easy to communicate with and had a very simple process for checking in and checking out. The cottage was cozy and I felt like I just wanted to settle in for a while.
Superhost
A classic three-story guest house is set against a twilight sky, featuring white architectural details. The front porch offers ample space, framed by greenery. A ladder and additional lighting elements are visible, indicating ongoing improvements, while a warm glow from outdoor lights enhances the evening scene.
Guesthouse in Greenwich
4.93 out of 5 average rating, 14 reviews

Lost in Decision Forest Guesthouse

ChyRating, 5 stars2 weeks ago
Such a charming place and very peaceful! My friends and I had a great weekend.
Top guest favorite
Guesthouse in Guilford
4.99 out of 5 average rating, 89 reviews

Page Guest House

ReneeRating, 5 stars4 months ago
We were in town for a family Christmas party and were very happy staying at The Page Guest House. It was the perfect choice, especially since my 91-year-old mother was with me. The walk-in shower and the small step to get in made it easy. As former residents of Guilford, I highly recommend this centrally located, cozy guest house to anyone visiting the area.

Guest house rentals with a washer and dryer

Guest favorite
A winding asphalt driveway leads towards a white cottage, framed by lush greenery. A serene sunset casts golden hues across the sky and reflects off the wet surface, creating a tranquil atmosphere in the peaceful environment.
Guesthouse in Litchfield
4.93 out of 5 average rating, 55 reviews

The Blacksmith Cottage

JoyceRating, 5 stars1 week ago
Beautiful place and very quick response if needed anything at all. Was a great location for us and very spacious
Guest favorite
Guesthouse in Norwich
4.91 out of 5 average rating, 56 reviews

Brand new & close to casinos with HOT TUB

JustinRating, 5 stars3 weeks ago
Beautiful and peaceful. Perfect place to stay to get out of town for a day. Highly recommended
Top guest favorite
A shared backyard features a firepit surrounded by six Adirondack chairs, creating a cozy gathering spot. The grassy area is complemented by trees and a red shed, with the main house visible in the background under a bright sky.
Guesthouse in Stonington
5 out of 5 average rating, 220 reviews

Super Adorable Cottage + Fire pit + King Bed!

AbigailRating, 5 stars5 days ago
The king mattress made both my husband and I happy, which doesn't happen often away from home. The house was as pictured and had all the amenities. Deborah made sure that we had read the description of the loft stairs once she understood our kids would be staying up there. She was very helpful in finding a lost stuffed animal after we left as well.
Guest favorite
Guesthouse in New Haven
4.8 out of 5 average rating, 83 reviews

New Haven Pizza Cozy Guest House 1 mile to yale

NatalieRating, 5 stars1 week ago
I had a very peaceful stay. The area was quiet and as a light sleeper, I appreciated that. The decor was attractive and I loved the subway tile, sunken kitchen sink, and beautiful counter top. Everything worked fine and the hosts were easy to reach. There’s a nice organic market about three minutes walk away with good prices; it was so convenient to pick up a few groceries. I also appreciated the parking spot right in front of entry door! I definitely recommend this place!
Guest favorite
A spacious living area is presented with a large flat-screen TV mounted on a white entertainment unit. A soft gray sofa sits nearby, and a decorative area rug enhances the room's aesthetic. Natural light streams in through a front door adorned with a glass panel.
Guesthouse in Watertown
4.82 out of 5 average rating, 22 reviews

Private studio guesthouse

LeonardoRating, 5 stars1 week ago
very nice and quiet location, host was responsive and kind and the pictures match the actual place. without light pollution you get a very nice view of the night sky, amazing for night walks especially when taking into account the quiet neighborhood 10/10 would stay again :)
Top guest favorite
A serene outdoor space is presented with two umbrellas providing shade over wooden lounge chairs. A picnic table is positioned nearby, while lush green grass and blooming hydrangeas create a tranquil setting, inviting relaxation and enjoyment of nature.
Guesthouse in Stonington
4.97 out of 5 average rating, 70 reviews

Merry Hall Farmhouse

ChristianeRating, 5 stars6 months ago
Mara and Ross are wonderful hosts, very caring and helpful and lovely. Everything about our stay was perfect and super comfortable. There are very thoughtful touches throughout the house. The location is perfect - it's quiet and beautiful yet close to busier locales like Mystic. Five stars.
Guest favorite
Guesthouse in New Haven
4.94 out of 5 average rating, 296 reviews

Square 6ix

TylerRating, 5 stars1 month ago
My folks have stayed here a few times while visiting me and the family, and it's been great every time.
Top guest favorite
The interior space features a cozy living area with a sofa and coffee table, complemented by a vibrant area rug. A brick fireplace is located along one wall, while the kitchen area includes modern appliances and bar seating. Natural light floods through large windows.
Guesthouse in Stonington
4.97 out of 5 average rating, 278 reviews

True Artist Loft, 5 minutes to downtown Mystic

JamieRating, 5 stars2 weeks ago
The house was perfect, peaceful and cozy. It had all the essentials and was clean and comfortable. The location was fantastic, secluded and still only minutes away from the local attractions. We were slightly disappointed that we were unable to meet Sydney 🐕but we did see lots of birds, squirrels and wild turkeys! I would highly recommend this adorable guest house and we would definitely come back!

Destinations to explore