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

Guest favorite
Guesthouse in New London
4.97 out of 5 average rating, 107 reviews

Fully Renovated, Ocean Views, Fireplace & Beach

EvaRating, 5 stars3 weeks ago
Dawn’s place is private, well-appointed and in a fantastic location. You have an ocean view from the cottage, have access to a small semi-private beach, and a brief walk along the coast via the gorgeous neighborhood takes you to the larger Ocean Beach & boardwalk. Additionally there are very good restaurants, state parks, museums and pubs nearby. You’ll feel pampered by Dawn’s consideration and attention to detail and refreshed by the location and beaches.
Superhost
Guesthouse in Milford
4.92 out of 5 average rating, 205 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

JoyRating, 5 stars1 month 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.
Guesthouse in Montauk
4.61 out of 5 average rating, 95 reviews

Montauk Heaven, Beach & Woods

VincentRating, 5 stars3 days ago
Christine was an awesome host. We felt right at home and the place is a nice 15 min walk from the beach (or an even shorter drive). The house is beautiful and it felt personal and warm!
Guest favorite
Guesthouse in East Hampton
4.9 out of 5 average rating, 200 reviews

Beautiful Airy Barn in Springs

AdamRating, 5 stars4 weeks ago
Staying at Gillian’s place was amazing! It was very peaceful and tranquil and not too far from Main Street where we could shop and eat. The barn is quaint and homey and sits beautifully on a lawn. We loved our stay and will be returning in the future!
Guest favorite
Guesthouse in Barkhamsted
4.89 out of 5 average rating, 98 reviews

Farmington River Carriage House Pleasant Valley CT

WilliamRating, 5 stars2 days ago
Great stay! Lots of wildlife on the river. Will definitely come back.
Guest favorite
Guesthouse in Sprague
4.96 out of 5 average rating, 201 reviews

House on Little River / Writer Retreat

PamelaRating, 5 stars7 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!
Guest favorite
Guesthouse in Groton
4.94 out of 5 average rating, 443 reviews

Quiet studio with sleeping loft and deck

DiannaRating, 5 stars3 days ago
I will book again and again. The comfort of the bed and shower was fantastic. The appliances were updated and I will recommend this little piece of solitude Heaven. It’s like a wee nature refuge and Perfect location. The hosts were attentive and kind. A million thanks!
Superhost
Guesthouse in Shelter Island
4.96 out of 5 average rating, 115 reviews

Waterfront carriage house studio

FernRating, 5 stars7 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 Calverton
4.98 out of 5 average rating, 46 reviews

Private Luxe Cottage at Gates of Wine Country

ChristinaRating, 5 stars7 months ago
We had a wonderful stay at Carrie’s listing. When we first arrived, Carrie was still cleaning up so we were invited inside for a cup of wine. The airbnb had almost everything we needed (minus a microwave) and the property had super friendly chickens and every amenity needed for a stay-at-home vacation. Carrie was even kind enough to have us stay a little past check in to finish some work meetings. We appreciated everything and would recommend this to anyone coming to North Fork :)
Superhost
Guesthouse in Miller Place
4.73 out of 5 average rating, 52 reviews

Private guesthouse

RoselynRating, 5 stars4 weeks ago
Stayed here last November with a friend and was so glad I booked again! The place was clean, comfortable, and exactly as described. The host was responsive and made everything easy. Great location, too. Will definitely book again!
Guest favorite
Guesthouse in Norwich
4.94 out of 5 average rating, 54 reviews

Brand new & close to casinos with HOT TUB

JustinRating, 5 stars3 weeks ago
Beautiful and peaceful. Perfect place to stay to get out of town for a day. Highly recommended
Superhost
Guesthouse in Bridgehampton
4.82 out of 5 average rating, 79 reviews

Central Hamptons Guesthouse

JesseRating, 5 stars1 month ago
The Central Hamptons Guesthouse was a wonderful stay - it's a great location and a really charming house. Michael was a very communicative host, and overall it was a seamless, easy, relaxing weekend.
Superhost
Guesthouse in Hampton Bays
5 out of 5 average rating, 4 reviews

Hill Coast Cottage: Freshly Renovated

MelissaRating, 5 stars6 months ago
The pictures really don’t do it justice , the place is adorable. The kitchen has all new appliances, and it has every amenity you could need for a long or short stay.
Top guest favorite
Guesthouse in Pomfret
5 out of 5 average rating, 46 reviews

Cottage in Quiet Corner. Four miles from town.

NathanRating, 5 stars1 week ago
We loved our stay with Gary and Cindy! Cindy met us and showed us around. She kindly offered books for our kids and showed us her beautiful plants. They have lots of grandkids so they were happy to let our kids run free in their yard with their dogs, which my kids loved. The kids loved the little cubby hole beds and the cottage was comfortable and cozy. Cindy even had muffins and flowers awaiting us in the cottage. Highly recommend!
Guest favorite
Guesthouse in New Haven
4.8 out of 5 average rating, 83 reviews

New Haven Pizza Cozy Guest House 1 mile to yale

NatalieRating, 5 stars4 days ago
I had a very peaceful stay. The area was quiet and as a light sleeper, I appreciated that. The decor was attractive and I loved the subway tile, sunken kitchen sink, and beautiful counter top. Everything worked fine and the hosts were easy to reach. There’s a nice organic market about three minutes walk away with good prices; it was so convenient to pick up a few groceries. I also appreciated the parking spot right in front of entry door! I definitely recommend this place!
Top guest favorite
Guesthouse in Wading River
5 out of 5 average rating, 53 reviews

North Country Cottage

Nicole Rating, 5 stars3 weeks ago
Wonderful place to stay in wading river! Hosts were excellent and their place was cozy. Recommend to anyone needing a place to stay in the area.

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Rocky Hill
4.93 out of 5 average rating, 14 reviews

Camellia Springs - Solace & Rest

MatthewRating, 5 stars1 month 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 favorite
Guesthouse in Shelter Island
4.89 out of 5 average rating, 9 reviews

Stylish Studio Suite on Shelter Island

AnnaRating, 5 stars9 months ago
Kate’s place was perfect—down a quiet and private road but close to everything Shelter Island has to offer. The apartment was cozy and comfortable with all the necessities. Kate was very responsive when needed but you also have privacy. Lovely stay—I hope to come again!
Guest favorite
Guesthouse in Southold
4.91 out of 5 average rating, 57 reviews

Southold- Adorable 1 Bedroom Cottage

VictoriaRating, 5 stars1 month ago
Marta & Pete were great hosts. Left helpful instructions and a list of places in the area. The Cottage was definitely a great place to celebrate our anniversary. We wish we could have tried some of their oysters, but look forward to going back during the beach season when they're probably plentiful.
Superhost
Guesthouse in Hampton Bays
5 out of 5 average rating, 21 reviews

2 Bedroom Hamptons Waterfront Cottage Rental

BrianRating, 5 stars9 months ago
A quaint cottage that was sparkling clean. Access to the Peconic from a private dock with the available kayaks and canoes. There is a pristine built-in pool with new decking. There was a 10 minute drive to Hampton Bays town with great restaurants, grocery and shopping.
Guest favorite
Guesthouse in New Haven
4.94 out of 5 average rating, 296 reviews

Square 6ix

TylerRating, 5 stars4 weeks ago
My folks have stayed here a few times while visiting me and the family, and it's been great every time.
Guesthouse in Waterford
5 out of 5 average rating, 15 reviews

Waterfront Cottage on the Niantic River

StephenRating, 5 stars11 months ago
We had a wonderful time. The weather cooperated a couple of days so that we were able to have dinner on the deck overlooking the Niantic River. A big bonus was that we were within walking distance from the friend we were visiting. Matt was very friendly and helpful. The bed was comfortable. The kitchen was nicely stocked with dishes, utensils, etc. The starter coffee pods were a nice touch. The bathrooms were clean and spacious. We would definitely stay here again.
Guesthouse in Southampton
4.9 out of 5 average rating, 11 reviews

Southampton Village - Escape to Tranquility

MarionRating, 5 stars44 months ago
Southampton is just expensive so value is hard to judge. The pool is amazing. The home is a mix of old and new, but very comfortable. Beach is about 1.5 miles away and town just a little less.
Guest favorite
Guesthouse in Wallingford
5 out of 5 average rating, 18 reviews

Perfect guest house very private

DavidRating, 5 stars4 months ago
Don‘s place was spotless and private. Don himself was very easy to communicate with and responded almost immediately. We were happy to stay at his place and visit nearby relatives. We would recommend Don‘s place to anyone wanting a lovely, private and spotless place to stay.

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