Stay in the best homes in Middletown

Home spotlights in Middletown

Crop And Saddle

6 guests
4 bedrooms

Washington, Litchfield

Clued-up New Yorkers have slowly been turning their attention away from the Hamptons to this corner of countryside in Litchfield County. One step into this home, and we can see why they're making the swap.

The Captain's House

10 guests
4 bedrooms

Jamesport, North Fork

Mere steps from the beach, this four-bedroom farmhouse sleeps ten and is ideal for a large family getaway. Rustic it may be, but the interiors don’t skimp on style – white walls and pops of colour lend it a modern Scandinavian vibe.

The Pond House

5 guests
3 bedrooms

Woodstock, New York

This Woodstock residence is one for the design-savvy folk. Once a studio belonging to acclaimed realist painter Reginald Marsh, the space has been transformed into a stunning family home.

The Golden Dawn

4 guests
2 bedrooms

Litchfield, Northwest Hills Planning Region

There are some homes that simply capture your heart from the moment you arrive. And we won’t be surprised if it’s love at first sight when you see this charming Colonial saltbox house.