Guesthouse vacation rentals in Long Island

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Long Island guesthouse rentals

Family-friendly guest house rentals

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

Fully Renovated, Ocean Views, Fireplace & Beach

JohnRating, 5 stars3 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 stars3 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 favorite
Guesthouse in Suffern
4.96 out of 5 average rating, 133 reviews

Hiking trails steps from your door!

AriRating, 5 stars6 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.
Top guest favorite
Guesthouse in South Salem
4.94 out of 5 average rating, 285 reviews

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

LisaRating, 5 stars3 days ago
Jonathan and Amy were the perfect hosts. Super friendly and resourcesful. The property is beautiful and so peaceful which was perfect for our down time as we were in town for a three-day wedding. We enjoyed breakfast with the family of deer that live in the back field and so many beautiful birds. The apartment is so quaint, very clean and has everything that we needed. The beds were super comfortable. It was decorated to the age of the property which we loved! It was a great find and we highly recommend the apartment and will surely book again if ever in the area.
Guest favorite
Guesthouse in Huntington Station
4.85 out of 5 average rating, 131 reviews

2 large bedrooms in cozy little neighborhood.

KathyRating, 5 stars3 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 favorite
Guesthouse in Groton
4.94 out of 5 average rating, 453 reviews

Quiet studio with sleeping loft and deck

JessicaRating, 5 stars1 week 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 favorite
Guesthouse 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
Guesthouse 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 house rentals with a patio

Superhost
Guesthouse in Miller Place
4.76 out of 5 average rating, 59 reviews

Private guesthouse

LoriRating, 5 stars3 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 favorite
Guesthouse in Brewster
4.94 out of 5 average rating, 144 reviews

Sherwood Barn - close to ski mountain

VelluRating, 5 stars1 week ago
We had a great time staying for a week at the Sherwood Barn ❤️ Thank you!
Superhost
Guesthouse 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.
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 stars2 weeks 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 favorite
Guesthouse in Shirley
4.95 out of 5 average rating, 84 reviews

La casita J place

StephanieRating, 5 stars1 week ago
We absolutely loved our stay. Unfortunately, we booked on a much colder day so we weren’t able to take full advantage of the pool— but even then, being able to sit outside in the patio is nice. The family gave us so much privacy. Would absolutely love to come back on a warmer day!
Guest favorite
Guesthouse in Highlands
4.9 out of 5 average rating, 101 reviews

The Bungalow at Sandy Hook House

AjurahRating, 5 stars2 weeks 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 favorite
Guesthouse in Wading River
4.98 out of 5 average rating, 61 reviews

North Country Cottage

RachelRating, 5 stars3 days ago
Wonderful stay! Thanks for everything!!
Guest favorite
Guesthouse in Madison
4.97 out of 5 average rating, 104 reviews

Beachy & Bright Coastal Escape - 5 Mins to Beach

JuliaRating, 5 stars3 days ago
We can’t say enough good things about our stay! The space was beautifully decorated and had everything we needed for a weekend at the beach. They also provided thoughtful touches like a beach bag loaded with towel and a map to make it extra special. We loved how walkable it was to the beach and enjoying a cocktail on the porch after a hot day. Madison has some amazing restaurants and shops too - a perfect long weekend. Thank you for being such welcoming hosts!

Guest house rentals with a washer and dryer

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 Morristown
4.96 out of 5 average rating, 227 reviews

Private Guest House

AlyssaRating, 5 stars3 days ago
Amy and her husband welcomed us when we arrived and were super friendly and responsive with messaging! The place was just as described and the perfect accommodations for a weekend in NJ. A nice surprise was the enclosed backyard for our dogs to explore! Wifi was a bit spotty, but definitely not a deal breaker for us.
Guest favorite
Guesthouse in Easton
4.84 out of 5 average rating, 103 reviews

Entire Guest House at Fox Pond Farm.

ColinRating, 5 stars1 week 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
Guest favorite
Guesthouse in Fairfield
4.95 out of 5 average rating, 21 reviews

The Creekside Cottage

ChristinaRating, 5 stars1 week 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 favorite
Guesthouse in Stonington
5 out of 5 average rating, 223 reviews

Super Adorable Cottage + Fire pit + King Bed!

Barbara Rating, 5 stars2 weeks 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 favorite
Guesthouse 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 favorite
Guesthouse in Bridgewater
4.93 out of 5 average rating, 103 reviews

Carriage House in The Valley

NancyRating, 5 stars2 weeks 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.
Top guest favorite
Guesthouse in Stonington
4.98 out of 5 average rating, 286 reviews

True Artist Loft, 5 minutes to downtown Mystic

GinaRating, 5 stars3 weeks ago
Second time stay here and I loved it! It’s such a cute, private and homey place. I enjoy every minute there and Meg is so accommodating and sweet! I will absolutely book here again

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