Guest house holiday rentals in Middlesex County

Find and book unique guest house rentals on Airbnb

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Popular amenities for guest house rentals in Middlesex County

Family-friendly guest house rentals

Guest favourite
Guest house in New London
4.97 out of 5 average rating, 109 reviews

Fully Renovated, Ocean Views, Fireplace & Beach

JohnRating, 5 stars2 weeks ago
Dawn set the bar high with this Carriage House. Fully stocked, updated, comfy, quiet, impeccably clean, high end everything. This was our first stay at an airbnb, I can't imagine they are all this new and this nice. Next time business or pleasure takes us up your way we hope to stay here. Thanks, J&B
Superhost
Guest house in Milford
4.92 out of 5 average rating, 206 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

JoyRating, 5 stars2 months ago
Nice ground floor apartment across the street from the beach and 2 blocks from the state park. Love the outdoors. And Delores and her brother were amazing. Friendly, responsive, and helpful.
Guest favourite
Guest house in Norwalk
5 out of 5 average rating, 70 reviews

Cottage by the Sea

CharlieRating, 5 stars2 weeks ago
Just like the photos; very nice, well kept separate cottage adjacent to garage, beautifully manicured grounds. very clean bathroom and kitchen. Hosts were very accommodating and helpful.
Guest house in Montauk
4.62 out of 5 average rating, 98 reviews

Montauk Heaven, Beach & Woods

KateyRating, 5 stars1 week ago
We loved staying at Christine’s place! Great location, great deck to sit outside and enjoy the weather, and not too far from the beach. She even came in person to be sure check in went smoothly. Definitely would stay here again!
Guest favourite
Guest house in East Hampton
4.9 out of 5 average rating, 211 reviews

Beautiful Airy Barn in Springs

NadineRating, 5 stars4 days ago
10000/10 recommend. Amazing Airbnb, beautiful pool, near east Hampton, Montauk, Parrish art museum, Dan Flavin institute, longhouse reserve, pollock krasner house. Easy check in, VERY safe neighborhood, Gilliam and her husband were kind and helpful.
Guest favourite
Guest house in Barkhamsted
4.89 out of 5 average rating, 102 reviews

Farmington River Carriage House Pleasant Valley CT

JamesRating, 5 stars2 weeks ago
A cozy spot that comfortably houses three adults, it's right on the river so it's perfect for fishing. While it feels remote, there are amenities close by like restaurants and grocery stores. And Bruce was a fantastic host, very friendly and helpful. I have no doubt we'll return.
Guest favourite
Guest house in Sprague
4.96 out of 5 average rating, 201 reviews

House on Little River / Writer Retreat

PamelaRating, 5 stars9 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
Guest house in Glastonbury
4.77 out of 5 average rating, 96 reviews

59 Old Maids Lane pool house

LinnaeRating, 5 stars6 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 house rentals with a patio

Guest favourite
Guest house in Norwich
4.91 out of 5 average rating, 67 reviews

Brand new & close to casinos with HOT TUB

MattRating, 5 stars2 weeks ago
Great little place to stay, just was not aware that it was attached to a main house. Thought it was its own place other than that was very nice.
Top guest favourite
Guest house in Pomfret
5 out of 5 average rating, 49 reviews

Cottage in Quiet Corner. Four miles from town.

MaggieRating, 5 stars1 month ago
Gary and Cindy have one of the most special spaces I’ve ever stayed in. The house has so much character, super functional and the property is outstanding - we especially loved the adorable cubbies (I’m 6’1” and I had enough space to stretch out!) Gary and Cindy were so lovely, welcoming and absolute pleasures to chat with! They have wonderful recommendations for local hiking trails and places to eat. I would come back to Cindy and Gary’s in a heartbeat, it was one of the most memorable places I’ve ever stayed!
Guest favourite
Guest house in East Hampton
4.84 out of 5 average rating, 57 reviews

Your Own Barn Loft Suite Among the Treetops

RhylieRating, 5 stars4 days ago
The loft was a home away from home. My mom was visiting for a week, and I needed a place for her and I to stay as my home is not big enough. The place was peaceful, and the bonus was that it was dog friendly— my mom has to see her granddog! The hosts were very welcoming, and I loved how responsive they were. The space had plenty of necessary items and the kitchen was perfect for making meals at “home”. If you are looking for something in the area, look no further!
Top guest favourite
Guest house in Litchfield
5 out of 5 average rating, 53 reviews

Guesthouse at Bantam Woods - 2 bedrooms

ShelleyRating, 5 stars1 day ago
This is one of those places you want to rave about so everyone out there looking for a truly special stay knows to book it right away if they find it available…but, you also hate to shout too loud because you would love to be able to keep it a secret so it’s always open when you want to return! 😀 Nestled back away from the road, this spot really has to be seen (and heard!) to truly appreciate it! We visited in June and after a very rainy season, the grass and trees were just so green and the flowers so full of color. You only have to listen for a bit to hear the songs of more birds than you could name, and the soft rushing of the nearby stream. A true escape. Central heat/air, new washer and dryer, drip or Keurig coffee, wi-fi and ability to stream on the TV, Bluetooth speaker to play your music, board games and SO many books, comfy blankets and slippers, roomy closets for longer stays and simply one of THE kindest, and most thoughtful hosts we have had the pleasure to meet!
Top guest favourite
Guest house in Norwalk
5 out of 5 average rating, 21 reviews

Waterfront Getaway - Norwalk, CT

HillaryRating, 5 stars2 weeks ago
Loved our stay here! The apartment was very clean and comfortable, and had everything we needed. Excellent location - nice view and very walkable both to Sono and East Norwalk. Communication was easy and clear, thank you! Only thing I would note is that there is a flight of stairs to get to the entrance which was a little tricky with our luggage and stroller (we were traveling with a baby) - didn’t detract from how great our stay was, and would still book again despite that.
Top guest favourite
Guest house in Cornwall
5 out of 5 average rating, 12 reviews

Fishing Lodge on Large Country Estate

BillRating, 5 stars3 weeks ago
We were day hiking the AT in the Kent to Cornwall area and stayed 3 nights at the Lodge. The lodge was comfortable, roomy and equipped with everything we needed. Brooke was great to talk with and very responsive to our requests and questions. My only regret is that we did not have enough time to explore the grounds of the estate which appear to be amazing and have a very interesting history. Highly recommended
Top guest favourite
Guest house in Clinton
4.95 out of 5 average rating, 38 reviews

Studio Cottage

KellyRating, 5 stars6 days ago
Looked just like the photos. Private space. Clean and tidy, had a few essentials including coffee! She was very responsive and gave East to follow directions for checking in. Provided great recommendations for nearby places. Location was exactly what we were looking for. Would highly recommend.
Top guest favourite
Guest house in Essex
5 out of 5 average rating, 46 reviews

Adorable 2 bedroom guesthouse in Essex village

AishwaryaRating, 5 stars3 weeks ago
Reninca and Scott’s home is absolutely wonderful. Peaceful, well catered. My family and I were so happy with this stay - definitely raised the bar!

Guest house rentals with a washing machine and dryer

Guest favourite
Guest house in Rocky Hill
4.93 out of 5 average rating, 15 reviews

Camellia Springs - Solace & Rest

MatthewRating, 5 stars3 months ago
I stayed at Camellia Springs across three days and really enjoyed the space, but Camille is what makes the place extra special. She had great communication and made sure my check-in went smoothly including a tour of some of the features and local suggestions. She also double checked I had everything I needed throughout my stay. I got the impression she wanted me to feel at home. The space itself is great on its own. The bathroom is spacious and there’s a separate mirrored space besides the sink itself that’s like a makeup vanity. The toilet is at the far end of the bathroom tucked around a corner so it’s definitely set up for multiple people to be getting ready without feeling crowded. The shower also has good pressure without being stingingly sharp. The open living space between the living room and kitchen makes for a great hangout. Overall, if I could find a space like this with a host like Camille in all my travel locations, I’d choose it every time.
Top guest favourite
Guest house in Madison
4.97 out of 5 average rating, 77 reviews

The Barn by the Sound

DianeRating, 5 stars4 weeks ago
Vicky and Peter's little barn apartment was perfectly located for us, close to the beach and we so enjoyed their well landscaped and beautiful property, the birds in the trees and views out the window. The furniture and bed were comfortable and kitchen had all that we needed. They thoughtfully left us a six pack of nice water in the fridge and a pretty little bouquet of her garden flowers on the table. Vicky was friendly and gracious when we saw her in her yard and ready to assist if we needed any thing. They also made the effort to move patio furniture to a location for our use. I would definitely recommend Vicky and Peter's airbnb for others.
Top guest favourite
Guest house in Westerly
4.99 out of 5 average rating, 95 reviews

Ocean Shire Coastal Retreat + Beach Pass

AmyRating, 5 stars1 week ago
Barbara’s place was really lovely. Clean, very comfortable, private, and near beaches and restaurants/shops. She provided an excellent binder with instructions as well as recommendations for things to do in the area. I would absolutely recommend staying here if you’re looking for a RI getaway.
Guest favourite
Guest house in Easton
4.84 out of 5 average rating, 103 reviews

Entire Guest House at Fox Pond Farm.

ColinRating, 5 stars4 days ago
A group of us stayed here for a wedding nearby. Durelle was super communicative and helpful the whole time we were there. We didn't get to spend much time there and due to the weather we didn't hang outside too much but the property was beautiful and seemed like a great place for a summer getaway with the pool & firepit
Superhost
Guest house in Southbury
4.93 out of 5 average rating, 70 reviews

The Nest. Large studio in the Woods.

AnkitaRating, 5 stars3 weeks ago
Comfortable, quiet, and a beautiful little location in the woods!
Top guest favourite
Guest house in Bethel
5 out of 5 average rating, 18 reviews

Tranquil getaway cottage in charming neighborhood

EuripidesRating, 5 stars1 month ago
"Lovely, peaceful stay! Erika was a responsive and kind host. The place was clean, cozy, and perfect for relaxing. Would definitely return!" Highly recommend !
Top guest favourite
Guest house in Stonington
5 out of 5 average rating, 223 reviews

Super Adorable Cottage + Fire pit + King Bed!

Barbara Rating, 5 stars1 week ago
This cottage was very comfortable, we had everything we needed, it was easy to get to off of Interstate 95. We enjoyed the shops at Old Mystic Village and the ride into downtown Mystic was a breeze. The beds and pillows were super comfortable. We enjoyed sitting out on the front porch. This cottage was well appointed and centrally located.
Guest favourite
Guest house in New Haven
4.82 out of 5 average rating, 94 reviews

New Haven Pizza Cozy Guest House 1 mile to yale

ConnieRating, 5 stars2 days ago
I booked Luis's place on extremely short notice, but everything was neat and ready for my arrival nonetheless. It was exactly as described and matched the pictures. I appreciated the ease of check-in and check-out. There were particular amenities that I enjoyed. For example, the bedding was super cozy, and I could log in to my own streaming services without worrying about logging out (it would automatically do so once I checked out). I also appreciated the recommendations for restaurants and places to visit. It made it less overwhelming to choose good restaurants and places to visit. Thanks, Luis, for a cozy stay!

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