Vacation Rentals in The Hamptons | The Roundtree, Amagansett Skip to main content
Guest Room, The Roundtree, Amagansett, Hotel in Hamptons

Luxury Cottage Rentals

Our 5 stand-alone cottages on the property are the perfect option for families, friends and our favorite four-legged guests. They offer the added comfort of privacy and truly give the feeling of a home away from home vacation. 

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3 Bedroom Cottage with Kitchen and Dining Room, The Roundtree, Amagansett, Hotel in Hamptons

Three Bedroom Cottage

Our three bedroom cottage, the largest accommodation on our property, is over 1,000 square feet and can accommodate up to eight guests. With an open and airy feel, this 250 year old cottage features a cathedral ceiling, gas fireplace, three bedrooms, two full bathrooms, a separate living room with a Queen sofa bed, a dining room that can seat up to eight people, and a fully equipped European style kitchen. The cottage has been thoughtfully renovated to reflect the modern vision of The Roundtree, Amagansett fused with historic design details nestled throughout the property. This cottage features wide plank hardwood floor, modern bathrooms with a European premium vanity, walk-in shower and rain showerhead. There is one bedroom with a custom made King bed, one with a custom made Queen bed and one with two Twin beds.  Consider our three bedroom cottage your families’ home away from home, with luxurious amenities such as Frette linens, Matouk towels, Nespresso machine, and a mini bar stocked with complimentary snacks and beverages upon arrival. 

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Guest Room, The Roundtree, Amagansett, Hotel in Hamptons

Two Bedroom Cottage

Designed to preserve the historic beauty of the architecture, this charming cottage features beautiful original wood beam on its ceilings.  With 2 separate bedrooms and 1 shared bath, this cozy cottage is perfect for a family with young children. Luxurious amenities include Frette linens, Matouk towels, Nespresso coffee machine, and a mini bar stocked with complimentary snacks and beverages upon arrival.

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Barn Living Room, The Roundtree, Amagansett, Hotel in Hamptons

One Bedroom Cottage

Our beautifully designed one bedroom cottage features an airy cathedral ceiling, gas fireplace and a private garden for reading, relaxing, and enjoying a morning cup of coffee (or evening glass of wine!) in total privacy. This cottage has been updated with wide plank hardwood floor, modern bathroom with European premium vanity, walk in shower and rain showerhead.  With an open and spacious feel, the cottage features one bedroom with a custom made King bed and French doors opening up to a separate living room with a Queen sofa bed. Luxurious amenities also include Frette linens, Matouk towels, Nespresso coffee machine, and a mini bar stocked with complimentary snacks and beverages upon arrival.

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Bathroom, The Roundtree, Amagansett, Hotel in Hamptons

Studio Cottage

With its open layout and airy cathedral ceiling, our studio cottages are the perfect option for couples, friends and our favorite four-legged guests.  Located in our idyllic back lawn, the studio cottages have been thoughtfully renovated and reflect the modern vision of The Roundtree, Amagansett fused with historic design details.  Each cottage has been updated with wide plank hardwood floor, modern bathroom with European premium vanity, walk-in shower and rain showerhead and features a custom made King or Queen bed and a sitting area. Select studio cottages also feature a Queen sofa bed in the sitting area. Luxurious amenities include Frette linens, Matouk towels, Nespresso coffee machine, and a mini bar stocked with complimentary snacks and beverages upon arrival.