Guesthouse vacation rentals in Connecticut

Find and book unique guesthouse rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Connecticut guesthouses

Family-friendly guesthouses

Guest favourite
Guesthouse in New London
4.97 out of 5 average rating, 107 reviews

Fully Renovated, Ocean Views, Fireplace & Beach

EvaRating, 5 stars1 month 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 favourite
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 favourite
Guesthouse in Barkhamsted
4.89 out of 5 average rating, 99 reviews

Farmington River Carriage House Pleasant Valley CT

AnnRating, 5 stars6 days ago
A functionally designed 2 bdrm, 3 bed apartment in a quiet guest cottage on a pleasantly landscaped property with a pleasing/calming view of the Farmington River from the living room. Bruce and spouse are very warm, friendly, and interesting people. You will enjoy your stay!
Guest favourite
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
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 favourite
Guesthouse in Granby
4.89 out of 5 average rating, 233 reviews

The Loft @ Lost Acres ~ A Peaceful Rural Escape!

AlisonRating, 5 stars4 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
Private room in New Haven
4.82 out of 5 average rating, 204 reviews

Amadeus "English Garden Studio"

SanaeRating, 5 stars1 week 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!
Guesthouse in Norwalk
5 out of 5 average rating, 21 reviews

Guest Cottage in Rowayton

Alfonso JamesRating, 5 stars10 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.

Guesthouses with a patio

Top guest favourite
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 favourite
Guesthouse in Fairfield
4.94 out of 5 average rating, 16 reviews

The Creekside Cottage

JimRating, 5 stars1 day ago
At the risk of creating too much interest in Rowena's Creekside Cottage, we thoroughly our stay with Rowena. Her Cottage is a great space right on Pine Creek. Each morning we were serenaded by the many different songbirds that make the Creek and the Marsh behind it home and one morning we were treated to an Osprey flyover. A walk on Fairfield's LI Sound beaches or, a stroll in central Fairfield are are super close, making the Cottage a great get-away spot.
Top guest favourite
Guesthouse in Pomfret
5 out of 5 average rating, 47 reviews

Cottage in Quiet Corner. Four miles from town.

NathanRating, 5 stars2 weeks 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 favourite
Guesthouse in Sharon
4.94 out of 5 average rating, 107 reviews

Cottage with a Waterfall View

JeffreyRating, 5 stars2 weeks 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 favourite
Guesthouse in Madison
4.97 out of 5 average rating, 100 reviews

Chic Coastal Escape - 5 Mins to the Beach

MelissaRating, 5 stars2 weeks 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 favourite
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
Guesthouse in Greenwich
4.93 out of 5 average rating, 14 reviews

Lost in Decision Forest Guesthouse

ChyRating, 5 stars3 weeks ago
Such a charming place and very peaceful! My friends and I had a great weekend.
Top guest favourite
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.

Guesthouse rentals with a washer and dryer

Guest favourite
Guesthouse in Litchfield
4.93 out of 5 average rating, 56 reviews

The Blacksmith Cottage

RebeccaRating, 5 stars6 days ago
Our second stay at this fantastic home. Beautiful surroundings and comfy house.
Guest favourite
Guesthouse in Norwich
4.9 out of 5 average rating, 58 reviews

Brand new & close to casinos with HOT TUB

JustinRating, 5 stars1 month ago
Beautiful and peaceful. Perfect place to stay to get out of town for a day. Highly recommended
Top guest favourite
Guesthouse in Stonington
5 out of 5 average rating, 220 reviews

Super Adorable Cottage + Fire pit + King Bed!

AbigailRating, 5 stars1 week 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 favourite
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 favourite
Guesthouse in Watertown
4.83 out of 5 average rating, 24 reviews

Private studio guesthouse

GabrielleRating, 5 stars1 day ago
I stayed at Ray’s AirBnB with my boyfriend as a stop on our way home. The space was beautiful! We enjoyed the large TV in front of the bed. Since most of our trip was busy, we enjoyed the relaxation time. Ray’s space was simple, but beautiful. The high ceilings made the space feel bigger and welcoming. The bed was comfortable as well. Ray’s AirBnB was the perfect place to stop and we are hoping to visit again!😊
Top guest favourite
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 favourite
Guesthouse in New Haven
4.94 out of 5 average rating, 298 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 favourite
Guesthouse in Stonington
4.97 out of 5 average rating, 279 reviews

True Artist Loft, 5 minutes to downtown Mystic

AmandaRating, 5 stars2 weeks ago
My boyfriend and I fell in love with this place as soon as we opened the door. It's quaint, tasteful, and very well cared for. We had absolutely no issues during our stay, and not a single complaint. The perfect getaway to clear your mind and rest, or work on a small craft, or learn something new by picking up one of the many beautiful books they have available to guests of the loft. There are also pamphlets available for things to do in the area if you are looking to explore, eat, or shop. Do yourself a favor and experience the magic of this loft for yourself!

Destinations to explore