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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.

46 West Neck Road, Shelter Island; Rosehip Realty
Price: $20,000 (MD-LD)
The Lowdown: This is a very pretty renovated 1875 farmhouse with a spacious porch in front and another 16' porch right off the master bedroom. The house has four bedrooms, two baths, in about 2500sf. There's a really charming vintage-style kitchen, three kayaks, and an outdoor shower. It's even close to the ferry.

3645 Noyac Road, Sag Harbor; Simon Harrison
Price: $100,000 (MD-LD)
The Lowdown: Wow, look at that stunning kitchen! But we're not sure if we're more impressed by the kitchen or the views right onto Noyack Bay. The house, which is 2300sf, four bedroom, three baths, is close to Sag Harbor Village and the bay beach. Spend all summer staring out the window spellbound.

Holy Crap!
44 Sayres Path, Wainscott; Saunders
Price: $400,000 (MD-LD)
The Lowdown: This place really earns the sobriquet Holy Crap! The exterior is jaw-dropping. About 2.7 acres in Wainscott includes a 70' infinity pool with a trickling waterfall and an outside sunken terrace that overlooks the pool. Another outside dining area is covered with a wisteria trellis; it adjoins an outdoor kitchen and faces a vegetable and herb garden (a live-in caretaker and gardener is included in the rental price to ensure your cilantro doesn't go to seed). We're slightly less in love with the interior—except for that vaulted sitting room, of course. There's seven bedrooms and 10.5 baths (two steam showers) in about 10,500sf, with a state of the art media room. We'd never go inside, though.