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Guest house holiday rentals in The Hamptons
Find and book unique guest house rentals on Airbnb
Top-rated guest house rentals in The Hamptons
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for guest house rentals in The Hamptons
Family-friendly guest house rentals
![](https://a0.muscache.com/im/pictures/910477e1-6f33-46f4-a937-ab9727e4de6c.jpg?im_w=720)
Guest house in Cherry Grove, Fire Island
4.92 out of 5 average rating, 64 reviewsOne Bedroom Cottage in Cherry Grove
![](https://a0.muscache.com/im/pictures/b89af0b6-bae7-407c-b90a-b1c760888f14.jpg?im_w=720)
Guest house in Sag Harbor
4.89 out of 5 average rating, 99 reviewsCharming 2BR Cottage, Walk to Town
![](https://a0.muscache.com/im/pictures/f75a3f16-329e-4811-923a-6ee4446d1751.jpg?im_w=720)
Guest house in Milford
4.92 out of 5 average rating, 193 reviewsSilversands Air-Bnb You’re right Here!
![](https://a0.muscache.com/im/pictures/20365571/a03296d9_original.jpg?im_w=720)
Guest house in East Hampton
4.9 out of 5 average rating, 189 reviewsBeautiful Airy Barn in Springs
![](https://a0.muscache.com/im/pictures/miso/Hosting-18295175/original/bc11d0ea-af9e-4354-a477-d09536ccc462.jpeg?im_w=720)
Guest house in Westhampton
4.33 out of 5 average rating, 9 reviewsCharming Westhampton SandDollar Cottage. AC.
Guest house rentals with a patio
![](https://a0.muscache.com/im/pictures/df42c08b-46a0-43da-8cb5-b9b0153944e0.jpg?im_w=720)
Guest house in Shirley
4.95 out of 5 average rating, 42 reviewsLa casita J place
![](https://a0.muscache.com/im/pictures/miso/Hosting-645330000827247796/original/12e550bd-66c6-4963-989e-7c22c95b286b.jpeg?im_w=720)
Guest house in Calverton
4.96 out of 5 average rating, 28 reviewsPrivate Luxe Cottage at Gates of Wine Country
![](https://a0.muscache.com/im/pictures/miso/Hosting-718839407677972293/original/3abaa82e-c3a5-4b38-9162-5dcb66a030ad.jpeg?im_w=720)
Guest house in Hampton Bays
5 out of 5 average rating, 3 reviewsRetro Mid-Century Cottage 1/2 mile to CPI
![](https://a0.muscache.com/im/pictures/miso/Hosting-659310021352793789/original/d71a01c9-2aeb-4ef4-8cee-d462d4e09985.jpeg?im_w=720)
Guest house in Madison
4.96 out of 5 average rating, 73 reviewsBeachy & Bright Carriage House/5 min walk to Beach
![](https://a0.muscache.com/im/pictures/miso/Hosting-695487702985716401/original/7ab4b959-e19d-4e02-87d6-684bb5e15a6f.jpeg?im_w=720)
Guest house in Madison
4.95 out of 5 average rating, 56 reviewsThe Rising Tide Cottage
![](https://a0.muscache.com/im/pictures/miso/Hosting-54193772/original/76606293-666e-46ad-bcf6-2374bf65916c.png?im_w=720)
Guest house in Guilford
5 out of 5 average rating, 63 reviewsPage Guest House
![](https://a0.muscache.com/im/pictures/40e4db3a-b8df-4c9e-885b-5b591db249bd.jpg?im_w=720)
Guest house in Hampton Bays
Hill Coast Cottage: Freshly Renovated
![](https://a0.muscache.com/im/pictures/ab27f108-da1e-40d7-af92-1c423ef6445f.jpg?im_w=720)
Guest house in Southold
Picture perfect 2 bedroom, 1 bath private cottage
Guest house rentals with a washing machine and dryer
![](https://a0.muscache.com/im/pictures/740b837a-145c-45cd-9ad1-78f6338963ef.jpg?im_w=720)
Guest house in Southold
4.95 out of 5 average rating, 43 reviewsSouthold- Adorable 1 Bedroom Cottage
![](https://a0.muscache.com/im/pictures/e49a6856-8e90-4e9b-b9c7-1135e75c2f18.jpg?im_w=720)
Guest house in Madison
5 out of 5 average rating, 60 reviewsThe Barn by the Sound
![](https://a0.muscache.com/im/pictures/14287c19-7a09-4511-aaa3-c2d954393b13.jpg?im_w=720)
Guest house in Clinton
4.94 out of 5 average rating, 195 reviewsThe Gardener's Cottage Dog friendly/ weekly/montly
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Guest house in Setauket- East Setauket
4.85 out of 5 average rating, 135 reviewsNewly Renovated Water Front Cottage in Setauket
![](https://a0.muscache.com/im/pictures/miso/Hosting-1027506555715222737/original/f9f0c8a2-6a43-40bb-8880-700e076723ea.jpeg?im_w=720)
Guest house in Guilford
4.88 out of 5 average rating, 16 reviewsThe Little Blue Cottage
![](https://a0.muscache.com/im/pictures/miso/Hosting-685347106682566593/original/81d18a9c-f44b-417a-8e46-289f36fea976.jpeg?im_w=720)
Guest house in Fire Island
5 out of 5 average rating, 6 reviewsCharming Fire Island Guest Cottage
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6NTA3OTk3OTk%3D/original/9452c536-a7a3-4eda-904c-fc810cd06b2f.jpeg?im_w=720)
Guest house in Hampton Bays
5 out of 5 average rating, 14 reviewsOne Bedroom Hamptons Waterfront Cottage
![](https://a0.muscache.com/im/pictures/miso/Hosting-50067328/original/5fcd16bf-84b9-4554-b5a0-cc30e30990f1.jpeg?im_w=720)
Guest house in East Quogue
4.91 out of 5 average rating, 22 reviewsHamptons Two Bedroom Cottage
Destinations to explore
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