Guesthouse holiday rentals in Middlesex County

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Middlesex County guesthouses

Family-Friendly guesthouses

Superhost
Guesthouse 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
Superhost
Guesthouse in Shelter Island
4.96 out of 5 average rating, 115 reviews

Waterfront carriage house studio

FernRating, 5 stars8 months ago
John was a perfect host! Friendly, responsive and made us feel welcome. I took my 9 year old son and we had a great time fishing off the dock and kayaking. The kitchenette is lacking if you want to cook any meals but it didn’t matter in our case. Absolutely beautiful location!
Superhost
Guesthouse 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
Private room in New Haven
4.82 out of 5 average rating, 207 reviews

Amadeus "English Garden Studio"

JeremyRating, 5 stars2 weeks ago
Enjoyed our three night stay at Remy's English Garden Studio. The walk to campus was perfectly pleasant, and an added benefit is the Studio's proximity to off-campus amenities like a number of bakery/cafes, right around the corner. Next time I'm in New Haven, will check to see if English Garden Studio is available.
Top Guest favourite
Guesthouse in Fairfield
4.96 out of 5 average rating, 194 reviews

Southport, CT across from BEACH

ValRating, 5 stars1 week ago
Jeff’s place was a hidden gem. It was private, close to the beach and town and the home was safe, clean and well designed. Jeff was kind and super responsive. There is a reason this place is always booked. I highly recommend staying here and can’t wait to return!
Guest favourite
Guesthouse 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!

Guesthouses with a patio

Guest favourite
Guesthouse 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
Guesthouse 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!
Superhost
Guesthouse in East Hampton
4.84 out of 5 average rating, 57 reviews

Your Own Barn Loft Suite Among the Treetops

RhylieRating, 5 stars1 day 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
Guesthouse in Litchfield
5 out of 5 average rating, 52 reviews

Guesthouse at Bantam Woods - 2 bedrooms

EricaRating, 5 stars3 weeks ago
This was our second time booking with Laurie and, as with our first stay, we were thoroughly impressed! Laurie is incredibly communicative, welcoming and helpful. Her space is meticulous, warm and very comfortable. Grateful for another wonderful opportunity to spend time in such a lovely spot!
Top Guest favourite
Guesthouse in Cornwall
5 out of 5 average rating, 12 reviews

Fishing Lodge on Large Country Estate

BillRating, 5 stars2 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
Guesthouse in Clinton
4.95 out of 5 average rating, 38 reviews

Studio Cottage

KellyRating, 5 stars3 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.
Guest favourite
Guesthouse in New Haven
4.82 out of 5 average rating, 93 reviews

New Haven Pizza Cozy Guest House 1 mile to yale

JennRating, 5 stars1 day ago
We felt at home in Luis’s pizza themed cozy place. Luis was so amazing and I highly recommend his place to explore the world around Yale University. Thank you!
Top Guest favourite
Guesthouse 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
Guesthouse 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.
Guest favourite
Guesthouse in Madison
4.97 out of 5 average rating, 77 reviews

The Barn by the Sound

DianeRating, 5 stars3 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
Guesthouse 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
Guesthouse in Easton
4.84 out of 5 average rating, 103 reviews

Entire Guest House at Fox Pond Farm.

ColinRating, 5 stars1 day 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
Guesthouse 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
Guesthouse in Bethel
5 out of 5 average rating, 18 reviews

Tranquil getaway cottage in charming neighborhood

EuripidesRating, 5 stars4 weeks 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
Guesthouse 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.
Superhost
Guesthouse in Southold
4.92 out of 5 average rating, 59 reviews

Southold- Adorable 1 Bedroom Cottage

NikkiRating, 5 stars2 days ago
This is an absolute gem of a find. It’s close to numerous vineyards and a seaside port for deckside drinks and quaint shopping spots. The ferries to Southhampton is only ten minutes away and the ferry to New London is also only about 20 minutes away. The cottage is super cute and has everything you need. Perfect.

Destinations to explore