
Guest house holiday rentals in Middlesex County
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Top-rated guest house rentals in Middlesex County
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Family-friendly guest house rentals

Fully Renovated, Ocean Views, Fireplace & Beach
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

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.

Cottage by the Sea
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.

Montauk Heaven, Beach & Woods
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!

Beautiful Airy Barn in Springs
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.

Farmington River Carriage House Pleasant Valley CT
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.

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!

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
Guest house rentals 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 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!

Waterfront Getaway - Norwalk, CT
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.

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.

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.

New Haven Pizza Cozy Guest House 1 mile to yale
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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- 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