
Guesthouse holiday rentals in Middlesex County
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Top-rated Guesthouses in Middlesex County
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Middlesex County guesthouses
Family-Friendly guesthouses

59 Old Maids Lane pool house
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

Waterfront carriage house studio
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!

Chic Coastal Retreat: Modern Apt Steps from Beach
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.

Amadeus "English Garden Studio"
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.

Southport, CT across from BEACH
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!

House on Little River / Writer Retreat
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

Brand new & close to casinos with HOT TUB
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.

Cottage in Quiet Corner. Four miles from town.
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!

Your Own Barn Loft Suite Among the Treetops
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!

Guesthouse at Bantam Woods - 2 bedrooms
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!

Fishing Lodge on Large Country Estate
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

Studio Cottage
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.

New Haven Pizza Cozy Guest House 1 mile to yale
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!

Adorable 2 bedroom guesthouse in Essex village
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

Camellia Springs - Solace & Rest
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.

The Barn by the Sound
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.

Ocean Shire Coastal Retreat + Beach Pass
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.

Entire Guest House at Fox Pond Farm.
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

The Nest. Large studio in the Woods.
Comfortable, quiet, and a beautiful little location in the woods!

Tranquil getaway cottage in charming neighborhood
"Lovely, peaceful stay! Erika was a responsive and kind host. The place was clean, cozy, and perfect for relaxing. Would definitely return!" Highly recommend !

Super Adorable Cottage + Fire pit + King Bed!
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.

Southold- Adorable 1 Bedroom Cottage
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.
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- Rentals with a fire pit Middlesex County
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Six Flags New England
- Cooper's Beach, Southampton
- Napeague Beach
- Shinnecock Hills Golf Club
- Walnut Public Beach
- TPC River Highlands
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Bushnell Park
- Quotonset Beach
- Ninigret Beach
- Groton Long Point South Beach
- Wildemere Beach