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 Tivoli
4.94 out of 5 average rating, 248 reviews

Light-filled guest cottage

ElyseRating, 5 stars2 weeks ago
Gorgeous place in a beautiful town. About a thirty minute walk (or 4 minute drive!) right into downtown with cute shops and restaurants. The cottage is beautiful, clean and so cozy. Highly recommend.
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.
Top Guest favourite
Guesthouse in Suffern
4.96 out of 5 average rating, 133 reviews

Hiking trails steps from your door!

AriRating, 5 stars4 months ago
Peter's place is THE perfect stay for a couple (plus dog) planning a visit to Rockland County. The cottage is extremely clean and incredibly cozy. The surroundings are beautiful, with the property well set back from the road and bordering Harriman State Park. Suffern and its restaurants aren't far and there's easy access to the Palisades Parkway to go anywhere else nearby. I grew up in the county and visit my parents on a regular basis. Any time I can't stay at their home, Peter's place will be my go-to from now on.
Guest favourite
Guesthouse in Huntington Station
4.85 out of 5 average rating, 127 reviews

2 large bedrooms in cozy little neighborhood.

DanaRating, 5 stars1 month ago
Our band travels up to play in Long Island twice a year. Liz's place was a great, affordable place for us to spend the weekend. We had everything we needed. And, the location was not just close to lots of great restaurants and coffee shops (which we love) but also close to the event that were booked to play. Our band would very much like to stay there again :)
Superhost
Guesthouse in Stormville
4.98 out of 5 average rating, 172 reviews

Hudson Valley Cottage with Pond Access

JamieRating, 5 stars6 months ago
This bungalow was a magical place to spend an autumn weekend visiting family and the beautiful Hudson valley area. We enjoyed morning walks around the pond with our pup and our coffee. Wish we had time to use the fire pit! Hammocks and bed was comfy, shower and kitchen were clean and lovely! Thanks so much a for a great stay! Would certainly recommend!
Guest favourite
Guesthouse in Sprague
4.96 out of 5 average rating, 201 reviews

House on Little River / Writer Retreat

PamelaRating, 5 stars8 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 favourite
Guesthouse in Groton
4.94 out of 5 average rating, 443 reviews

Quiet studio with sleeping loft and deck

DiannaRating, 5 stars1 week 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!

Guesthouses with a patio

Superhost
Guesthouse in Miller Place
4.73 out of 5 average rating, 52 reviews

Private guesthouse

RoselynRating, 5 stars1 month 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 favourite
Guesthouse in Brewster
4.94 out of 5 average rating, 140 reviews

Sherwood Barn - close to ski mountain

JenniferRating, 5 stars2 weeks ago
Beth was very kind and responsive. Great place to stay!
Top Guest favourite
Guesthouse in Gardiner
4.99 out of 5 average rating, 174 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

PatriciaRating, 5 stars1 month ago
This place was a perfect weekend get away for myself and husband. Plenty of space for the two of us. The place was nicely, decorated and fully furnished with accessories if you wish to cook. I enjoyed the spaces between the outside patio as well as the hot tub. Bill was great with giving suggestions of local places, even though I was a local myself.. if you’re looking for a quiet getaway this is your place.
Guest favourite
Guesthouse in Franklin Township
4.92 out of 5 average rating, 26 reviews

Private guesthouse

SabrinaRating, 5 stars1 month ago
This place is quiet and very private, as someone in the area for work this is exactly what I am looking for. I work night shift and the host was understanding about odd sleeping hours and adjusted check out time for me. Wonderful all around, will definitely be back!
Top Guest favourite
Guesthouse in Sharon
4.94 out of 5 average rating, 107 reviews

Cottage with a Waterfall View

JeffreyRating, 5 stars1 week ago
The cottage is beautiful and such a surprise when you open the front door - the magical stream is right out the window. Although the cottage is close to the road you would never know it - the back patio is just perfect!! An easy drive to a a number of small and lovely quintessentially New England villages. We would highly recommend Jeff and Elizabeth's cottage!
Guest favourite
Guesthouse in Tomkins Cove
4.81 out of 5 average rating, 21 reviews

The cottage at Oasis Cove

DanielRating, 5 stars2 months ago
We wanted a quiet weekend, and we got a whole lot more. Andrew and Mynor were amazing hosts!! From the complimentary beverages to the assistance with snow removal, their service was incredible. The photos did not do justice to the place; the decor was great, and the place was spotless. We will definitely be back!!
Guest favourite
Guesthouse in Montclair
4.95 out of 5 average rating, 19 reviews

Mountaintop Carriage House with Tennis Court

FrancescaRating, 5 stars1 month ago
The carriage house was a lovely stay and very charming. Everything was clean, comfy and as described. The hosts were very friendly and detailed. It’s so quiet at night, but close enough to town for all amenities. The view of the city from the back patio was a plus!
Guest favourite
Guesthouse in Asbury Park
5 out of 5 average rating, 17 reviews

Carriage House by Surfers Beach Asbury Park

ChristaRating, 5 stars8 months ago
We whole heartedly enjoyed our stay. The apartment was very well appointed and so comfortable. We especially appreciated how quick and easy it was to walk to the beach or any of the great restaurants in the area. Regine and her family are exceptional hosts!

Guest house rentals with a washing machine and dryer

Top Guest favourite
Guesthouse in South Salem
4.94 out of 5 average rating, 282 reviews

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

AlicjaRating, 5 stars2 days 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 Mamaroneck
4.91 out of 5 average rating, 159 reviews

Your Modern Guest Wing Near NYC

ChayenneRating, 5 stars3 weeks ago
I had a wonderful stay ! The home was clean, comfortable, and exactly as described in the listing. The location was perfect. The host very responsive and made check-in super easy. I would definitely stay here again and highly recommend it to anyone visiting the area!
Guest favourite
Guesthouse in Beacon
4.94 out of 5 average rating, 397 reviews

Cozy Mountainside Suite - Minutes from Beacon

DwainRating, 5 stars3 weeks ago
This is a beautiful place and exactly what my wife and I needed for a long weekend away! The barn is so cozy and we felt right at home . The hot tub was a nice treat on the cool evenings and the beautiful view. But by far the best part was the animals living below us that we could give snacks to throughout the day and see through the living space windows. Would definitely recommend this to anyone that loves horses and donkeys!
Guest favourite
Guesthouse in Stanfordville
4.93 out of 5 average rating, 179 reviews

Eco Cottage in the Woods

SusanRating, 5 stars6 months ago
Upon entry, my architect husband said "Cute Cottage; Susan you did it again." Plenty of room for a couple in their mid-seventies, and a Millennial daughter. The cottage is very well insulated such that I didn't have to run the heat except for fifteen minutes at bedtime in mid-October, yet there is a big south-facing sliding door in each of the rooms where the sun and moon shines through. Beautiful woodland falls away from the cottage and small patio beyond the sliding doors, and moonlight is magic on all the leaves. If we had more time we would have investigated the many books in the shelving. We will find excuses for coming back to the area and will stay here again.
Superhost
Guesthouse in Dover Plains
4.88 out of 5 average rating, 112 reviews

Spilt Milk Cottage - Hudson Valley, NY

LorenzoRating, 5 stars4 months ago
We loved the cottage. If anything it was even cuter in person than in the pictures. Communication was perfect and the place was very well thought out. We enjoyed our stay, I’d recommend it and come back here in the future!
Guest favourite
Guesthouse in New Haven
4.94 out of 5 average rating, 297 reviews

Square 6ix

TylerRating, 5 stars1 month ago
My folks have stayed here a few times while visiting me and the family, and it's been great every time.
Top Guest favourite
Guesthouse in Ulster Park
4.99 out of 5 average rating, 415 reviews

Escape to a Sleek, Serene Studio on the Riverbank

NinaRating, 5 stars2 weeks ago
I loved my stay here. I came up solo to work, sleep and relax. The unit itself is wonderful if you gravitate toward sunlight and thoughtful design. The mattress is fantastic and the place has everything you could hope for. The view is stunning and the outdoor space is adorable with plenty of place to spread out both indoors and outdoors. It is peaceful and quiet. You will sleep like a rock. The studio was spotless. There is some hiking options a short walk away and Kingston is about ten minutes or less (the waterfront section). Shannon is an ideal host and has thought of everything. Do not hesitate to book this if you want to relax and have a million dollar river view in a stylish and comfortable studio. I hope to be back for sure!
Top Guest favourite
Guesthouse in Stonington
4.97 out of 5 average rating, 278 reviews

True Artist Loft, 5 minutes to downtown Mystic

JamieRating, 5 stars2 weeks ago
The house was perfect, peaceful and cozy. It had all the essentials and was clean and comfortable. The location was fantastic, secluded and still only minutes away from the local attractions. We were slightly disappointed that we were unable to meet Sydney 🐕but we did see lots of birds, squirrels and wild turkeys! I would highly recommend this adorable guest house and we would definitely come back!

Destinations to explore