Guesthouse vacation rentals in The Hamptons

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for The Hamptons guesthouses

Family-friendly guesthouses

Guest favourite
Guesthouse in Cherry Grove, Fire Island
4.92 out of 5 average rating, 76 reviews

One Bedroom Cottage in Cherry Grove

DanielRating, 5 stars7 months ago
Fernando was a wonderful host and the location couldn’t be beat!! Steps to all the shops and restaurants and also convenient for the beach. Highly recommend!
Guesthouse in Montauk
4.61 out of 5 average rating, 95 reviews

Montauk Heaven, Beach & Woods

VincentRating, 5 stars3 days ago
Christine was an awesome host. We felt right at home and the place is a nice 15 min walk from the beach (or an even shorter drive). The house is beautiful and it felt personal and warm!
Guesthouse in Montauk
4.74 out of 5 average rating, 58 reviews

Wave Crest Oceanfront Cottage.

BrentRating, 5 stars35 months ago
Robert is a kind and gracious host. He left a bottle of wine with a charming note upon arrival. We had a few questions about the house and he was very prompt and helpful. The house is a sweet charming little cottage in Montauk on the steps from the beach at central air- it was perfect. We would definitely return in the future.
Guest favourite
Guesthouse in East Hampton
4.9 out of 5 average rating, 200 reviews

Beautiful Airy Barn in Springs

AdamRating, 5 stars4 weeks ago
Staying at Gillian’s place was amazing! It was very peaceful and tranquil and not too far from Main Street where we could shop and eat. The barn is quaint and homey and sits beautifully on a lawn. We loved our stay and will be returning in the future!

Guesthouses with a patio

Guest favourite
Guesthouse in Calverton
4.98 out of 5 average rating, 46 reviews

Private Luxe Cottage at Gates of Wine Country

ChristinaRating, 5 stars7 months ago
We had a wonderful stay at Carrie’s listing. When we first arrived, Carrie was still cleaning up so we were invited inside for a cup of wine. The airbnb had almost everything we needed (minus a microwave) and the property had super friendly chickens and every amenity needed for a stay-at-home vacation. Carrie was even kind enough to have us stay a little past check in to finish some work meetings. We appreciated everything and would recommend this to anyone coming to North Fork :)
Superhost
Guesthouse in Miller Place
4.73 out of 5 average rating, 52 reviews

Private guesthouse

RoselynRating, 5 stars4 weeks 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!
Superhost
Guesthouse in Bridgehampton
4.82 out of 5 average rating, 79 reviews

Central Hamptons Guesthouse

JesseRating, 5 stars1 month ago
The Central Hamptons Guesthouse was a wonderful stay - it's a great location and a really charming house. Michael was a very communicative host, and overall it was a seamless, easy, relaxing weekend.
Superhost
Guesthouse in Hampton Bays
5 out of 5 average rating, 4 reviews

Hill Coast Cottage: Freshly Renovated

MelissaRating, 5 stars6 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
Guesthouse in Fairfield
4.93 out of 5 average rating, 15 reviews

The Creekside Cottage

AndreRating, 5 stars2 months ago
Beautiful stay! Came to CT with 2 winterstorms back to back and below freezing temps. The place was cozy and warm the whole time! A great place to relax and watch the tide come in and out. And the "throne" room has a great view!
Guest favourite
Guesthouse in Shirley
4.96 out of 5 average rating, 75 reviews

La casita J place

KellyRating, 5 stars1 week ago
Quiet, nice spot.
Top guest favourite
Guesthouse in Clinton
4.97 out of 5 average rating, 31 reviews

Studio Cottage

CapriRating, 5 stars2 weeks ago
Staying at Casey’s cottage was very nice. It was peaceful and very comfortable. The neighborhood was very nice with easy access to I-95. She was a great host. Thank you for a lovely stay.
Guest favourite
Guesthouse in Madison
4.97 out of 5 average rating, 100 reviews

Chic Coastal Escape - 5 Mins to the Beach

MelissaRating, 5 stars6 days ago
Kelly was a very considerate, warm, and communicative hostess. The location was amazing with close proximity to Surf Club Beach, playground, Soccer, and baseball fields and adorable CT Shoreline towns. We also spent time at Jacob’s beach in the next town over called Guilford, land Essex which is just 15-20 minutes away. A few minutes by car are the Madison Beach Hotel and Christie’s restaurant. One of the best attributes for my family was the spacious backyard completely outfitted for children. The carriage house apartment, over the garage, is loft-like, very bright, and decorated sophistically. From street level, there are about 15 steps up to the open floor concept sitting area, bistro table, and kitchenette that lead to an en suite bedroom and bath plus a spacious deck off of the bedroom. My twins loved the plush bed! Thank you for such an enjoyable stay!

Guesthouse rentals with a washer and dryer

Superhost
Guesthouse in Fairfield
4.67 out of 5 average rating, 3 reviews

Fairfield Town/Beach "Story-Book" Cottage w/Pool

MelanieRating, 5 stars37 months ago
This Cottage was in the BEST location and had the perfect amenities for a long term stay with my two toddlers and our family dog. Would definitely recommend and would definitely return.
Top guest favourite
Guesthouse in Madison
4.97 out of 5 average rating, 75 reviews

The Barn by the Sound

AllisonRating, 5 stars4 months ago
Peter and Vicky’s place is a beautifully situated and thoughtful space. We felt completely at home and loved all of the nice touches that made our stay feel comfortable. We loved exploring the books made available and looking out the windows into the tree tops. Exploring the local area is easy with only a short walk to the beach or woodland area. Would highly recommend to anyone wanting a peaceful escape.
Guest favourite
Guesthouse in Shelter Island
4.89 out of 5 average rating, 9 reviews

Stylish Studio Suite on Shelter Island

AnnaRating, 5 stars9 months ago
Kate’s place was perfect—down a quiet and private road but close to everything Shelter Island has to offer. The apartment was cozy and comfortable with all the necessities. Kate was very responsive when needed but you also have privacy. Lovely stay—I hope to come again!
Guesthouse in Madison
5 out of 5 average rating, 6 reviews

Upper Deck Carriage House

BarbaraRating, 5 stars81 months ago
This place is fabulous—has the perfect amenities, is nicely decorated, and is the perfect location in Madison. We were in walking distance to “downtown” shopping district, restaurants, and the beach. The rental is very comfortable and relaxing. Great get-away. The host responds quickly to questions and left a great list of local restaurants.
Guest favourite
Guesthouse in Southold
4.91 out of 5 average rating, 57 reviews

Southold- Adorable 1 Bedroom Cottage

VictoriaRating, 5 stars1 month ago
Marta & Pete were great hosts. Left helpful instructions and a list of places in the area. The Cottage was definitely a great place to celebrate our anniversary. We wish we could have tried some of their oysters, but look forward to going back during the beach season when they're probably plentiful.
Guest favourite
Guesthouse in Bay Shore
4.87 out of 5 average rating, 31 reviews

Cozy Place

MelanieRating, 5 stars2 months ago
This place was a last minute pick for a last minute trip. Im definitely coming back again now that I will be traveling back and forth.
Superhost
Guesthouse in Hampton Bays
5 out of 5 average rating, 21 reviews

2 Bedroom Hamptons Waterfront Cottage Rental

BrianRating, 5 stars9 months ago
A quaint cottage that was sparkling clean. Access to the Peconic from a private dock with the available kayaks and canoes. There is a pristine built-in pool with new decking. There was a 10 minute drive to Hampton Bays town with great restaurants, grocery and shopping.
Guest favourite
Guesthouse in Madison
5 out of 5 average rating, 10 reviews

Flip-flop

suzanne Rating, 5 stars6 months ago
Absolutely love staying here. The guest house is perfect. It has everything you need & a beautiful upstairs bedroom. The location is phenomenal, in a gorgeous neighborhood right near the beach!! I highly recommend this wonderful home!!

Destinations to explore