
Guesthouse holiday rentals in Long Island Sound
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Top-rated Guesthouses in Long Island Sound
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Popular amenities for Long Island Sound guesthouses
Family-Friendly guesthouses

Light-filled guest cottage
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.

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.

Hiking trails steps from your door!
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.

2 large bedrooms in cozy little neighborhood.
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 :)

Hudson Valley Cottage with Pond Access
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!

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!

Quiet studio with sleeping loft and deck
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!

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!
Guesthouses with a patio

Private guesthouse
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!

Sherwood Barn - close to ski mountain
Beth was very kind and responsive. Great place to stay!

Red Barn Retreat - Shawangunk Mountains Getaway
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.

Private guesthouse
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!

Cottage with a Waterfall View
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!

The cottage at Oasis Cove
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!!

Mountaintop Carriage House with Tennis Court
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!

Carriage House by Surfers Beach Asbury Park
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

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

Your Modern Guest Wing Near NYC
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!

Cozy Mountainside Suite - Minutes from Beacon
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!

Eco Cottage in the Woods
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.

Spilt Milk Cottage - Hudson Valley, NY
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!

Square 6ix
My folks have stayed here a few times while visiting me and the family, and it's been great every time.

Escape to a Sleek, Serene Studio on the Riverbank
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!

True Artist Loft, 5 minutes to downtown Mystic
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!
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