
Guesthouse vacation rentals in The Hamptons
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouses in The Hamptons
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for The Hamptons guesthouses
Family-friendly guesthouses

One Bedroom Cottage in Cherry Grove
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!

Montauk Heaven, Beach & Woods
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!

Wave Crest Oceanfront Cottage.
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.

Beautiful Airy Barn in Springs
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

Private Luxe Cottage at Gates of Wine Country
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 :)

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!

Central Hamptons Guesthouse
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.

Hill Coast Cottage: Freshly Renovated
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.

The Creekside Cottage
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!

La casita J place
Quiet, nice spot.

Studio Cottage
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.

Chic Coastal Escape - 5 Mins to the Beach
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

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

The Barn by the Sound
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.

Stylish Studio Suite on Shelter Island
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!

Upper Deck Carriage House
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.

Southold- Adorable 1 Bedroom Cottage
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.

Cozy Place
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.

2 Bedroom Hamptons Waterfront Cottage Rental
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.

Flip-flop
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!!
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Dunewood
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- Seaside Beach
- Jennings Beach
- Amagansett Beach
- Blue Shutters Beach
- Shennecossett Beach
- Sunken Meadow State Park
- Connetquot River State Park Preserve
- Outer Beach at Smith Point County Park
- Long Island Aquarium
- Attawan Beach
- Groton Long Point Main Beach
- East Beach
- Things to do The Hamptons
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