Guesthouse vacation rentals in The Hamptons
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in The Hamptons
Guests agree: these guesthouse rentals 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 guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Cherry Grove, Fire Island
4.93 out of 5 average rating, 61 reviewsOne Bedroom Cottage in Cherry Grove
Guesthouse in Milford
4.92 out of 5 average rating, 191 reviewsSilversands Air-Bnb You’re right Here!
Guesthouse in East Hampton
4.9 out of 5 average rating, 187 reviewsBeautiful Airy Barn in Springs
Guesthouse in Westhampton
4.33 out of 5 average rating, 9 reviewsCharming Westhampton SandDollar Cottage. AC.
Guesthouse in Sag Harbor
4.88 out of 5 average rating, 94 reviewsCharming 2BR Cottage, Walk to Town
Guest house rentals with a patio
Guesthouse in Shirley
4.97 out of 5 average rating, 34 reviewsLa casita J place
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
Guesthouse in Hampton Bays
5.0 out of 5 average rating, 3 reviewsRetro Mid-Century Cottage 1/2 mile to CPI
Guesthouse in Hampton Bays
Hill Coast Cottage: Freshly Renovated
Guesthouse in Southold
Picture perfect 2 bedroom, 1 bath private cottage
Guesthouse in Westhampton Beach
4.79 out of 5 average rating, 14 reviewsTennis & Sea Escape
Guesthouse in Bellport
5.0 out of 5 average rating, 9 reviewsGuest House retreat with amazing pool !!!
Guesthouse in Miller Place
4.69 out of 5 average rating, 32 reviewsPrivate guesthouse
Guest house rentals with a washer and dryer
Guesthouse in Southampton
4.8 out of 5 average rating, 10 reviewsSouthampton Village Getaway
Guesthouse in Southold
4.95 out of 5 average rating, 40 reviewsSouthold- Adorable 1 Bedroom Cottage
Guesthouse in Southampton
4.88 out of 5 average rating, 42 reviewsModern Guesthouse
Guesthouse in East Quogue
GuestHouse - Tennis court side luxury
Guesthouse in Setauket- East Setauket
4.85 out of 5 average rating, 135 reviewsNewly Renovated Water Front Cottage in Setauket
Guesthouse in Hampton Bays
5.0 out of 5 average rating, 13 reviewsOne Bedroom Hamptons Waterfront Cottage
Guesthouse in Mount Sinai
4.6 out of 5 average rating, 5 reviewsGreat Outdoors Beach & Pool Welcome!
Guesthouse in East Quogue
4.91 out of 5 average rating, 22 reviewsHamptons Two Bedroom Cottage
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Martha's Vineyard Vacation rentals
- Newark Vacation rentals
- Montauk Vacation rentals
- Hoboken Vacation rentals
- New Haven Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- Boston Vacation rentals
- Guesthouse rentals New York
- House rentals New York
- Guesthouse rentals United States
- House rentals United States
- House rentals Manhattan
- Guesthouse rentals Manhattan
- Waterfront rentals The Hamptons
- Cottage rentals The Hamptons
- Beachfront rentals The Hamptons
- Rentals with a washer and dryer The Hamptons
- Mansion rentals The Hamptons
- Rentals with a patio The Hamptons
- Private suite rentals The Hamptons
- Rentals with pools The Hamptons
- Rentals with outdoor seating The Hamptons
- Luxury rentals The Hamptons
- Bed and breakfasts The Hamptons
- Bungalow rentals The Hamptons
- Rentals with beach access The Hamptons
- Rentals with a hot tub The Hamptons
- Apartment rentals The Hamptons
- Smoking-friendly rentals The Hamptons
- Rentals with an EV charger The Hamptons
- Kid-friendly rentals The Hamptons
- Monthly Rentals The Hamptons
- Rentals with a kayak The Hamptons
- Rentals with breakfast The Hamptons
- Condo rentals The Hamptons
- Family-friendly rentals The Hamptons
- Beach house rentals The Hamptons
- Pet-friendly rentals The Hamptons
- Farmstay rentals The Hamptons
- House rentals The Hamptons
- Rentals with a fire pit The Hamptons
- Villa rentals The Hamptons
- Fitness-friendly rentals The Hamptons
- Rentals with lake access The Hamptons
- Rentals with a fireplace The Hamptons
- House rentals Brooklyn
- Guesthouse rentals Brooklyn
- House rentals New York
- Guesthouse rentals New York
- House rentals Suffolk County
- Guesthouse rentals Suffolk County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes