Guest house holiday rentals in Long Island

Find and book unique guest house rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for guest house rentals in Long Island

Family-friendly guest house rentals

Guest favourite
Guest house 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
Guest house 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
Guest house 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
Guest house in Huntington Station
4.85 out of 5 average rating, 131 reviews

2 large bedrooms in cozy little neighborhood.

KathyRating, 5 stars2 weeks ago
Place was exactly as described, clean, comfortable, and quiet. Liz was flexible with checkin which was helpful since our flight got in early and we did not have a car for our luggage. We did bang our heads on the slanted ceilings a few times the first day, but we adjusted. Location is in a quiet neighborhood, we Uber’ed to eat and do other activities. We would stay again.
Guest favourite
Guest house in Groton
4.94 out of 5 average rating, 451 reviews

Quiet studio with sleeping loft and deck

JessicaRating, 5 stars2 days ago
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 favourite
Guest house in Atlantic Highlands
4.88 out of 5 average rating, 323 reviews

Private Cabin in Beautifully Landscaped Gardens

MarkRating, 5 stars6 months ago
We were in town for a concert in Red Bank and the cabin met our needs perfectly. Ideal accommodations for two people and we were able to bring our dog along. An easy stay in a very comfortable setting.
Superhost
Guest house in Shelter Island
4.96 out of 5 average rating, 115 reviews

Waterfront carriage house studio

FernRating, 5 stars9 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 favourite
Guest house in Sag Harbor
4.86 out of 5 average rating, 107 reviews

Charming 2BR Cottage, Walk to Town

MarinaRating, 5 stars11 months ago
We had a wonderful time enjoying the cottage! The hosts are extremely welcoming and very friendly. The cottage was the perfect amount of space and in a wonderful location. My friends and I are already discussing making this an annual trip!

Guest house rentals with a patio

Top guest favourite
Guest house in Greenwich
4.95 out of 5 average rating, 93 reviews

The Cottage in Greenwich

AndresRating, 5 stars1 week ago
Lovely place, really clean, beautiful and peaceful…will definitely stay back there when visiting the area.
Superhost
Guest house 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.
Guest favourite
Guest house in Brewster
4.94 out of 5 average rating, 144 reviews

Sherwood Barn - close to ski mountain

VelluRating, 5 stars6 days ago
We had a great time staying for a week at the Sherwood Barn ❤️ Thank you!
Superhost
Guest house in Hampton Bays
5 out of 5 average rating, 4 reviews

Hill Coast Cottage: Freshly Renovated

MelissaRating, 5 stars7 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.
Guest favourite
Guest house in Fairfield
4.95 out of 5 average rating, 21 reviews

The Creekside Cottage

ChristinaRating, 5 stars5 days ago
This cottage is absolutely lovely and peaceful. You have a view of the Long Island Sound across the street and the house sits on an inlet. We truly enjoy sitting on the back deck on the inlet water. There are ALWAYS people walking, riding bikes, jogging, walking dogs… etc Lots of delicious restaurants and stores so super close! We will definitely be booking here again in the future!
Top guest favourite
Guest house in Waccabuc
4.99 out of 5 average rating, 95 reviews

French Guest House in Waccabuc

AndrewRating, 5 stars4 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.
Top guest favourite
Guest house 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!
Top guest favourite
Guest house in Clinton
4.95 out of 5 average rating, 38 reviews

Studio Cottage

KellyRating, 5 stars6 days ago
Looked just like the photos. Private space. Clean and tidy, had a few essentials including coffee! She was very responsive and gave East to follow directions for checking in. Provided great recommendations for nearby places. Location was exactly what we were looking for. Would highly recommend.

Guest house rentals with a washing machine and dryer

Guest favourite
Guest house 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
Guest house in Morristown
4.96 out of 5 average rating, 226 reviews

Private Guest House

NancyRating, 5 stars1 week 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
Guest house in Mystic
4.98 out of 5 average rating, 627 reviews

Gorgeous Waterfront Getaway

EthanRating, 5 stars4 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!
Guest favourite
Guest house in Easton
4.84 out of 5 average rating, 103 reviews

Entire Guest House at Fox Pond Farm.

ColinRating, 5 stars4 days ago
A group of us stayed here for a wedding nearby. Durelle was super communicative and helpful the whole time we were there. We didn't get to spend much time there and due to the weather we didn't hang outside too much but the property was beautiful and seemed like a great place for a summer getaway with the pool & firepit
Top guest favourite
Guest house in Huntington Station
4.97 out of 5 average rating, 92 reviews

Modern fully updated 2nd Floor apartment

JayRating, 5 stars1 month ago
Manuel was a great host, very responsive and respectful. Anything I needed he was right there to assist. His place was also very beautiful and just what I needed. Its hosts like him who make Airbnb a great place, hope to stay in one of his properties again soon!
Top guest favourite
Guest house 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.
Guest favourite
Guest house in Bay Shore
4.85 out of 5 average rating, 34 reviews

Cozy Place

JenniferRating, 5 stars1 month ago
stayed here for a second time and it was amazing, very quiet and clean place, absolutely coming back when I'm back in the area 💕
Top guest favourite
Guest house in Bridgewater
4.93 out of 5 average rating, 102 reviews

Carriage House in The Valley

NancyRating, 5 stars1 week ago
This was our second stay at this cottage. We were so happy it was available for the weekend we needed because we loved the first stay! Neil is the perfect host and we truly appreciate his hospitality, including the delicious strawberries from his garden and the special kiddo activity area my granddaughter enjoyed so much. We hope this rental will be available for us again on our next New Jersey visit.

Destinations to explore