Guesthouse holiday rentals in Long Island Sound

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Long Island Sound guesthouses

Family-Friendly guesthouses

Guest favourite
Guesthouse in New London
4.97 out of 5 average rating, 109 reviews

Fully Renovated, Ocean Views, Fireplace & Beach

JohnRating, 5 stars1 week ago
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
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.
Top Guest favourite
Guesthouse in South Salem
4.94 out of 5 average rating, 283 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

AlicjaRating, 5 stars1 month ago
We were stunned by how magical this place was with all it's uniqueness of historic house. Spotless clean, spacious, very friendly owners. Our kids loved running around the back yard and playing board games that were provided. We would definitely come back, the only thing we regret is that we couldn't stay for longer, the area is very picturesque. many thanks!
Guest favourite
Guesthouse in Barkhamsted
4.89 out of 5 average rating, 102 reviews

Farmington River Carriage House Pleasant Valley CT

JamesRating, 5 stars2 weeks 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.
Superhost
Guesthouse in Stormville
4.97 out of 5 average rating, 174 reviews

Hudson Valley Cottage with Pond Access

ChelseaRating, 5 stars1 month ago
If you're looking for a private retreat in a gorgeous setting, this is your place. The property is stunning, super walkable grounds, and a gorgeous back patio. S.A. is a super host, and when we ran into an issue, he was quick to respond and help. We recommend this place, and intend to stay again in the future.
Guest favourite
Guesthouse in Beacon
4.94 out of 5 average rating, 400 reviews

Cozy Mountainside Suite - Minutes from Beacon

AnthonyRating, 5 stars1 week ago
My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.
Guest favourite
Guesthouse in Groton
4.94 out of 5 average rating, 449 reviews

Quiet studio with sleeping loft and deck

ValerieRating, 5 stars2 weeks ago
Cute and cozy place. Close to downtown Mystic. Definitely would stay again!
Guest favourite
Guesthouse in Oyster Bay
4.89 out of 5 average rating, 707 reviews

Cozy private cottage in Oyster Bay

SarahRating, 5 stars2 weeks ago
Very clean, nice area, and good communication from host. Definitely recommend!

Guesthouses with a patio

Superhost
Guesthouse in Miller Place
4.75 out of 5 average rating, 57 reviews

Private guesthouse

ChandlarRating, 5 stars3 weeks ago
Gunay was always available and responded to our needs and questions immediately.
Top Guest favourite
Guesthouse in Gardiner
4.99 out of 5 average rating, 175 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

GretchenRating, 5 stars1 month ago
Great experience! 2 wineries within 1 mile. Close to great hiking. William, was very accommodating with check in & check out time. Would highly recommend staying here. Very cute , clean and comfortable with get amenities.
Superhost
Guesthouse in Valley Stream
4.79 out of 5 average rating, 129 reviews

Cozy 2 BR guest suite very close to JFK, UBS Arena

RevatiRating, 5 stars2 weeks ago
Great place! Matches the description! Really close to the airport!
Top Guest favourite
Guesthouse in Waccabuc
4.99 out of 5 average rating, 94 reviews

French Guest House in Waccabuc

KikoRating, 5 stars2 weeks ago
Beautiful place! Very tranquil, wish we stayed for longer because the room was filled with books I would have loved to read :)
Guest favourite
Guesthouse in Accord
4.92 out of 5 average rating, 124 reviews

Tiny Horse Barn

LisaRating, 5 stars4 weeks ago
My husband and I arrived late, around 9:30pm, because we had commuted after work in NYC. Everything was impeccable. The home is perfect in some many ways. We felt very comfortable and got an amazing night's sleep. The following more we had to head out early to pick our daughter up from Binghamton. She stayed with us on our second night. Nicolette's and Tim's Tiny Horse Barn is so perfect. It is exact amount of space we needed. Even though the space is space, there were 5 tissue boxes in perfect locations. This may seem a small thing to some. But if you have allergies, it is SO appreciated. The kitchen was equipped with keurig coffee pods, creamers, sugar, tea kettle and more than everything we needed. Equally the bathroom was perfect. The beds were super comfortable as was the temperature. There were plenty of great restaurants nearby. The attention to detail is amazing. Everywhere there are little hints of horses, but not in an overwhelming way. We actually are having book sent :)
Top Guest favourite
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.
Guest favourite
Guesthouse in Highlands
4.9 out of 5 average rating, 101 reviews

The Bungalow at Sandy Hook House

AjurahRating, 5 stars1 week ago
We had a wonderful stay at Kathleen’s! It was a perfect location and close to everything! She was flexible with check in and check out and gave us recommendations for a rainy day. Our little girl even got to take home a little stuffy! Thanks for everything!
Top Guest favourite
Guesthouse in Wading River
4.98 out of 5 average rating, 59 reviews

North Country Cottage

ChristineRating, 5 stars6 days ago
Jen’s cottage was peaceful, comfortable and clean. I was traveling with my 83 year old dad who has mobility issues and needed a place to stay with a recliner. I was excited when Jen responded to my inquiry (very quickly I might add) that she would be able to accommodate. Not only did the property exceed expectations, it was immaculate and felt like home immediately. This cottage made our trip possible. I wish I could give Jen more than 5 stars!!!

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in Brooklyn
4.93 out of 5 average rating, 136 reviews

Amazing Views & Rooftop Deck - Safe - Parking Incl

Marie-ThereseRating, 5 stars4 days ago
We had a really good time staying at this place, everything was better than in the pictures, wonderful view, very clean apartment, I would rent it again!
Guest favourite
Guesthouse in Mamaroneck
4.9 out of 5 average rating, 164 reviews

Your Modern Guest Wing Near NYC

ConnieRating, 5 stars1 month ago
Had a great time at Shay and Sam’s luxurious cottage. Every aspect of this place is thoughtfully designed from the decor, lighting and bathroom spa, to the Frette sheets and towels making for an incredibly comfortable stay. The kitchenette is very compact but has just about everything needed, including a dishwasher. A lovely backyard and patio are an added bonus along with a ramp to the property’s entrance. Located in a beautifully manicured and very quiet neighborhood across from the back of Harbor Island Park, the property is about a 25 minute walk from the train station via Mamaroneck Avenue-with its various shops, restaurants (Nonna Carola is not to be missed) a liquor store, and a small Italian market. We were pleasantly surprised to find a Trader Joe’s, bagel shop and the Nautilus diner about 20 minutes walking distance from the property as well. Communication with Sam was easy and very helpful. Would love to come back and definitely recommend a stay here.
Top Guest favourite
Guesthouse in Morristown
4.96 out of 5 average rating, 226 reviews

Private Guest House

NancyRating, 5 stars6 days ago
We had a wonderful time at Amy's place. It is perfectly situated near downtown Morristown, so we could take advantage of the restaurants and shops. It is also situated near the major highways, so we could get to other parts of New Jersey. We were in New Jersey for my husband's college reunion. The guest house was lovely with great amenities. I admit my favorite amenities were the many different types of coffee and the snacks. :) Amy is a great host. She is responsive and caring. She lives right on the premises so she is easily reachable. I highly recommend this place. We will definitely be back here next time we are visiting New Jersey!
Top Guest favourite
Guesthouse in Mystic
4.98 out of 5 average rating, 626 reviews

Gorgeous Waterfront Getaway

EmilyRating, 5 stars3 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 favourite
Guesthouse in Easton
4.84 out of 5 average rating, 102 reviews

Entire Guest House at Fox Pond Farm.

LucyRating, 5 stars10 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.
Top Guest favourite
Guesthouse in Olive
4.99 out of 5 average rating, 117 reviews

The Lily Cottage Guesthouse

AgnesRating, 5 stars1 week ago
The cottage was the perfect little get away! Tucked away in nature with plenty of scenes to enjoy nearby. Easily accessible to Kingston and Woodstock to dine out and shop. The cottage was clean and organized. Would definitely come back!
Top Guest favourite
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 Dover Plains
4.87 out of 5 average rating, 115 reviews

Spilt Milk Cottage - Hudson Valley, NY

JohnRating, 5 stars1 month ago
Easy to find, key pad entry, clean. Graham left some fresh eggs from his hens..nice touch. Quiet spot in a natural setting.

Destinations to explore