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Hamptons rentals run the gamut from modest to superlative, from reasonably priced to Holy Crap! Curbed bring you three rentals per destination in various prices as we head east. Today we look at homes in the peaceful towns of Shelter Island, Sag Harbor, and Wainscott.

3 Fairfield Lane , Wainscott; Saunders
Price: $75,000 (MD-LD)
The Lowdown: North of the highway, this charming barn is a great place to spend the summer. There are three bedrooms and two baths in 2200sf, with two fireplaces to warm up a chilly night; the yard is a half acre with pretty gardens and a pool.

163 Townline Road, Wainscott; BHS
Price: $200,000 (Aug)
The Lowdown: Wow. Nine acres on the ocean? Of course, you'll be paying for that privilege, and we're not at all sure there are any oceanviews from the property, which is more shabby than chic, although likable in an old-money way. The house, with six bedrooms and six baths, is 3500sf. There's a pool and tennis court and an in-ground trampoline, too.

Holy Crap!
5 Bay View Drive North, North Haven; Saunders
Price: $450,000 (MD-LD)
The Lowdown: This bayfront house offers 152 feet of private beach and a 140' deepwater dock. The house is 5200sf, not including a huge finished basement, and is simple and relaxing in style (love the copper surround on the fireplace). In all, there are six bedrooms, seven bathrooms and two half baths. Outside, there's a waterside saltwater pool and spa and a cabana with an outdoor kitchen.