20 Chestnut Street

20 Chestnut St is a 4 bed, 2.5 bath two-story getaway just 2hrs from NYC. Located within easy walking distance to all that Rhinebeck has to offer, historic architecture, boutique shopping, farmers’ markets, & a vibrant dining scene. Spend summer days lounging by the pool, fire up the grill for an al fresco dinner, or unwind on the covered porch with a morning coffee.

Nearby towns: Red Hook (10mins), Kingston (20mins), Woodstock (25mins), Saugerties (25mins), Millbrook (30mins), Hudson (35mins)

20 Chestnut St is a classic two-story Hudson Valley retreat just steps from Rhinebeck’s shops, restaurants and local attractions showcasing elegant bay windows, a charming brick chimney, lots of natural light throughout and a welcoming covered front porch.

The home offers two bright and inviting sitting rooms, one anchored by a cozy fireplace and plush seating for relaxed evenings in, and the other an equally comfortable space perfect for reading, conversation, or gathering with friends.

Just beyond, a sunlit dining room features a wooden table that seats six, ideal for shared meals, with a piano in the corner that adds character to the space. The kitchen features sage green cabinetry, light wood countertops, and a farmhouse-style sink set beneath a large window providing serene tree views.

Upstairs, you’ll find four inviting bedrooms and two bathrooms, one with a tub/shower combo and the other with a walk-in shower. The primary bedroom features a king size bed and a laptop friendly workspace, ideal for guests who may need to mix a little work with relaxation. The first guest bedroom presents a queen size bed while the second guest bedroom includes a double bed and a laptop friendly workspace. The fourth bedroom is great for kids with two twin beds.

20 Chestnut St delivers an authentic and memorable Hudson Valley stay, ideal for weekend getaways or trips with family and friends.

Please note that the pool closes every year seasonally, just around Labor Day, and reopens typically around Memorial Day.

At 20 Chestnut St, you’re perfectly positioned to experience the very best of Rhinebeck. Here are a few of our favorite local spots, all just moments from your stay.

Start with a memorable meal at Pretty to Think So or Bia, two local go-tos known for seasonal menus and warm, inviting spaces. For shopping, spend an afternoon browsing Hammertown Barn, Rhinebeck Mercantile, Zephyr on Hudson, and Land of Oz Toys, each offering a thoughtful mix of home goods, gifts, and one-of-a-kind finds.

History lovers shouldn’t miss the vintage aircraft and weekend airshows at the Old Rhinebeck Aerodrome. For rest and renewal, the renowned Omega Institute for Holistic Studies offers workshops and peaceful grounds open seasonally.

Indulge your sweet tooth at Samuel's Sweet Shop, find beautifully handcrafted jewelry at Adel Chefridi, and enjoy a relaxed tasting at Slow Fox Farm Brewery.