Guesthouse vacation rentals in Middlesex County

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Middlesex County guesthouse rentals

Family-friendly guest house rentals

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 favorite
Guesthouse in Norwalk
5 out of 5 average rating, 69 reviews

Cottage by the Sea

Agni MaRating, 5 stars3 months ago
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 !!!
Guesthouse in Montauk
4.62 out of 5 average rating, 98 reviews

Montauk Heaven, Beach & Woods

KateyRating, 5 stars6 days 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 favorite
Guesthouse in East Hampton
4.9 out of 5 average rating, 209 reviews

Beautiful Airy Barn in Springs

SusanRating, 5 stars6 days ago
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.
Guest favorite
Guesthouse in Barkhamsted
4.89 out of 5 average rating, 102 reviews

Farmington River Carriage House Pleasant Valley CT

JamesRating, 5 stars1 week 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 favorite
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!
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!

Guest house rentals with a patio

Guest favorite
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 favorite
Guesthouse in Pomfret
5 out of 5 average rating, 49 reviews

Cottage in Quiet Corner. Four miles from town.

MaggieRating, 5 stars4 weeks 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!
Top guest favorite
Guesthouse in Guilford
4.95 out of 5 average rating, 100 reviews

Guilford Lakes Cottage, with hot tub and fire pit.

DianeRating, 5 stars6 days ago
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!
Superhost
Guesthouse in East Hampton
4.84 out of 5 average rating, 56 reviews

Your Own Barn Loft Suite Among the Treetops

ChristineRating, 5 stars2 months ago
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!
Top guest favorite
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 favorite
Guesthouse in Norwalk
5 out of 5 average rating, 20 reviews

Waterfront Getaway - Norwalk, CT

HillaryRating, 5 stars1 week 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 favorite
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 favorite
Guesthouse in Clinton
4.95 out of 5 average rating, 38 reviews

Studio Cottage

KellyRating, 5 stars1 day 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 house rentals with a washer and dryer

Top guest favorite
Guesthouse in Mystic
4.98 out of 5 average rating, 626 reviews

Gorgeous Waterfront Getaway

EmilyRating, 5 stars2 days ago
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.
Guest favorite
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.
Guest favorite
Guesthouse in Easton
4.84 out of 5 average rating, 102 reviews

Entire Guest House at Fox Pond Farm.

LucyRating, 5 stars9 months ago
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.
Superhost
Guesthouse in Southbury
4.93 out of 5 average rating, 70 reviews

The Nest. Large studio in the Woods.

AnkitaRating, 5 stars2 weeks ago
Comfortable, quiet, and a beautiful little location in the woods!
Top guest favorite
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
4.91 out of 5 average rating, 58 reviews

Southold- Adorable 1 Bedroom Cottage

MeganRating, 5 stars1 month ago
It was the perfect spot for a getaway weekend. Easy access to wineries and restaurants. Would definitely stay again.
Guest favorite
Guesthouse in New Haven
4.82 out of 5 average rating, 92 reviews

New Haven Pizza Cozy Guest House 1 mile to yale

RabiyaRating, 5 stars4 days ago
I had a wonderful experience staying here during my trip to New Haven. The place was exactly as described clean, cozy, and really well-kept. It had everything I needed and felt super comfortable the entire time. What really stood out was how flexible and responsive the host was. They were easy to communicate with, quick to reply to any questions, and very accommodating with my schedule, which made everything so much easier and stress-free. (Also helped that they recommended us sooo many great things to do and places to eat) The location was also perfect close to Yale, restaurants, and local spots, but still in a quiet, safe neighborhood. I’d definitely stay here again and would recommend it to anyone looking for a smooth and pleasant stay in New Haven!
Guest favorite
Guesthouse in Watertown
4.88 out of 5 average rating, 34 reviews

Private studio guesthouse

MichelleRating, 5 stars3 days ago
Ray’s Airbnb is the perfect place to stay. It’s very clean, quiet and modern. Self check in was smooth and instructions were easy to understand. I highly recommend it!

Destinations to explore