Guesthouse vacation rentals in Long Island Sound

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Long Island Sound guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Tivoli
4.94 out of 5 average rating, 255 reviews

Light-filled guest cottage

JohnRating, 5 stars1 week ago
An incredibly charming, rustic, simple and comfortable small cottage, in a gorgeous rural setting. Just as advertised. It was perfect. Right across the road is Tivoli Bays, with beautiful trails for walking and hiking, and a small waterfall too. If you like, it's just a short walk to Broadway, the main strip in the village of Tivoli. You'll find a few restaurant options, a small market, sandwich shop, excellent coffee, and homemade ice cream. I met Yuko who couldn't be nicer and was a pleasure to chat with. A great experience all around - highly recommend booking a stay!
Guest favorite
Guesthouse in New London
4.97 out of 5 average rating, 109 reviews

Fully Renovated, Ocean Views, Fireplace & Beach

JohnRating, 5 stars2 weeks 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.
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 favorite
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 favorite
Guesthouse in Groton
4.94 out of 5 average rating, 450 reviews

Quiet studio with sleeping loft and deck

JessicaRating, 5 starstoday
This is the cutest Airbnb! Everything you need in a little niche of love, convenience, and comfort! A wonderful location and neighborhood! When visiting family, I will certainly be back to stay here. 💖
Guest favorite
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!
Top guest favorite
Guesthouse in Woodstock
5 out of 5 average rating, 388 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

BarbaraRating, 5 stars2 days ago
By far the best Airbnb experience I've ever had! Joni was an amazing host, and I also had the pleasure of meeting her husband Rob/seeing their unique, beautiful home. She was responsive and very helpful throughout my stay, and even taught this "non tech savvy" person how to operate the TV! The location is perfect- and in my case even more so, as I attended a family wedding at the Colony just a block away! Its a 5 minute walk to town, and at the same time very peaceful/private- a perfect combination. I fell in love with Woodstock and wish I could have stayed longer. I'll definitely be back, as there is much more to explore in the area- will definitely stay at Logstock when I return!

Guest house rentals with a patio

Superhost
Guesthouse in Miller Place
4.76 out of 5 average rating, 58 reviews

Private guesthouse

LoriRating, 5 stars2 weeks ago
This place is very peaceful, in a great area with lots of restaurants and shopping nearby. The guest house is extremely clean and there is no clutter. I really enjoyed my stay here and highly recommend this Airbnb if you ever want to get away to someplace peaceful but close enough where you can find things to do.
Top guest favorite
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
4.77 out of 5 average rating, 131 reviews

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

DyanaRating, 5 stars2 days ago
Anitas place was everything I needed for a weekend get away with a few friends for my bday. Her space is super clean and had everything we needed. Its also located in a cute and quiet neighborhood, in walking distance tona grocery store. We absolutely loved it and had an amazing time!
Top guest favorite
Guesthouse in Lawrence Township
4.93 out of 5 average rating, 353 reviews

Adorable studio cottage near Princeton

JohnRating, 5 stars1 week ago
Second time at Shawn's place, great place and location for our weekend. Will definitely be a repeat place for us. Shawn really makes us feel welcome.
Guest favorite
Guesthouse in North Providence
4.92 out of 5 average rating, 100 reviews

Hidden gem min from providence

AlejandraRating, 5 stars2 weeks ago
Maria’s place was great. We enjoyed our stay. Everything was really clean and bed was comfortable. Maria communicated very well. We would definitely stay there again.
Top guest favorite
Guesthouse in Waccabuc
4.99 out of 5 average rating, 95 reviews

French Guest House in Waccabuc

AndrewRating, 5 stars2 days ago
Lori's guest studio was magical. Located on a French Country estate in a beautiful rural area near Cross River, NY, the studio fronted a lovely pond with the rhythmic sound of the aerating fountain and nightly chorus of bullfrogs that transport you to another time and place. The studio is beautifully decorated and perfect for our short stay. The Keurig coffee maker was well stocked but came in a distant second place to Lori's recommended cafe and patisserie just 10 mins away. Next time we return (and we do plan to return!), we'll try to make some time to explore the area and leave the ever-rushing world behind.
Guest favorite
Guesthouse in Accord
4.92 out of 5 average rating, 124 reviews

Tiny Horse Barn

LisaRating, 5 stars1 month 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 favorite
Guesthouse in Guilford
4.95 out of 5 average rating, 100 reviews

Guilford Lakes Cottage, with hot tub and fire pit.

DianeRating, 5 stars1 week 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!

Guest house rentals with a washer and dryer

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

Amazing Views & Rooftop Deck - Safe - Parking Incl

Marie-ThereseRating, 5 stars1 week 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 favorite
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 favorite
Guesthouse in Mystic
4.98 out of 5 average rating, 627 reviews

Gorgeous Waterfront Getaway

EthanRating, 5 stars2 days ago
I had an absolutely perfect stay! The host was incredibly responsive and made everything seamless from start to finish. The place was spotless—super clean and well-maintained—and the views were absolutely stunning. I couldn’t have asked for a better experience. Highly recommended!
Top guest favorite
Guesthouse in Olive
4.99 out of 5 average rating, 119 reviews

The Lily Cottage Guesthouse

AnnieRating, 5 stars6 days ago
Really cute cottage for a getaway. Clean, well maintained. Enjoyed our stay here, would definitely recommend it to anyone looking to stay close by to sites for hiking and sightseeing!
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 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.
Top guest favorite
Guesthouse in Millerton
4.98 out of 5 average rating, 104 reviews

Loft in the Pines

KevinRating, 5 stars5 days ago
Mark and Rachel were awesome and I loved the place. Exactly what I was looking for to unplug and enjoy a few days off. Town is close by and has all the coffee, food and cocktails you will need. Will be staying here again.
Top guest favorite
Guesthouse in Ulster Park
4.99 out of 5 average rating, 418 reviews

Escape to a Sleek, Serene Studio on the Riverbank

HaroldRating, 5 stars1 week ago
With a few dozen AirBnB stays under my belt, I have to say Shannon's lovely home in Ulster Park, NY, is without a doubt, the most enjoyable I've ever had! Her home is immaculate and literally footsteps from the Hudson River! She has taken the time to create an immensely enjoyable retreat by providing all modern amenities (large screen smart TV, robust WiFi and a fully equipped modern kitchen. Her backyard is thoughtfully laid out, recognizing the River is the main attraction, and provides fabulous seating areas, accompanied by gas fueled fire pits! Truly amazing. I am sure I will be returning soon!

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