
Guesthouse vacation rentals in Middlesex County
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Top-rated guesthouse rentals in Middlesex County
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Popular amenities for Middlesex County guesthouse rentals
Family-friendly guest house rentals

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
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 !!!

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
A relaxing oasis! Bob and Gillian were so accommodating and considerate, always available with helpful advice. The barn is artistically appointed, the beds are very comfortable, and everything you need is available. We so enjoyed our time by the pool and especially the hammock! We felt right at home and would definitely come back.

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

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!
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!

Guilford Lakes Cottage, with hot tub and fire pit.
This home is absolutely perfect – the entire space is beautifully decorated, peaceful, and spotless from top to bottom. The beds are incredibly comfortable with high quality bedding. The kitchen is fully stocked with every conceivable item. The hot tub and fire pit are a relaxing way to end the day. You can tell Dean and Brenda take pride in maintaining the space and every little detail made it feel like a high-end stay. I’ll definitely be coming back and recommending it to friends!

Your Own Barn Loft Suite Among the Treetops
This is a fabulous place to stay! Beautifully decorated and all the comforts of home. Andrew and Jessica were gracious hosts and great communicators. We will definitely stay again!

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!

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.
Guest house rentals with a washer and dryer

Gorgeous Waterfront Getaway
This location is phenomenal! So quiet and peaceful. We loved our stay here, even with the rain & fog we had. The view to the water is unmatched. Super clear instructions on how to locate the property as it is tucked into a residential community. We will definitely be back.

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.

Entire Guest House at Fox Pond Farm.
Stayed at Scott and Durelle's guest house for my 30th birthday with 10 friends. Booked mostly for the pool to enjoy a hot August weekend, but unfortunately there was a huge tropical storm! We still enjoyed the spacious house, jumping into the pool in the rain, cooking on the grill in a moment of dry weather, and overall had a peaceful and fun weekend despite crazy weather! A testament to this great property - which is beautiful and just as in pictures.

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

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
It was the perfect spot for a getaway weekend. Easy access to wineries and restaurants. Would definitely stay again.

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!

Private studio guesthouse
We had a great and quiet stay with Ray. The Airbnb was very private, cozy and clean with dedicated parking spot, pathway and it’s easy access private entrance. The Airbnb is near everything, yet really quiet and it made our stay perfect. It’s also very close to the Hollister House Garden that we visited on our stay.
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Napeague Beach
- Six Flags New England
- Cooper's Beach, Southampton
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Seaside Beach
- Blue Shutters Beach
- Quotonset Beach
- Ninigret Beach
- Bushnell Park
- Jennings Beach
- Silver Sands Beach
- South Jamesport Beach
- Groton Long Point Main Beach