Penny Brook logo with a stylized signature above the website name and location in Litchfield County, Connecticut.

Perched on a small hill overlooking the picturesque town of Falls Village, Pennybrook Cottage offers the perfect retreat to experience the beauty of Litchfield County, CT. Enjoy local cafes, scenic hikes, farm stands, and antique shops, or stay in and unwind in our expertly curated New England getaway.

Welcome to Pennybrook

  • Living room with beige and white furniture, wooden accents, artwork and decorative items, two windows with white shades, natural light, and a patterned rug.

    The Cottage

    The perfect retreat for small families, couples, or friends seeking the tranquility of rural Connecticut, Pennybrook blends heritage charm with modern comfort for a stay that’s both stylish and inviting. Make it your escape to slow down, settle in, and feel at home.

    Step Inside

  • A red covered bridge over a flowing river surrounded by green trees and foliage on a sunny day.

    Things to Do

    From garden tours and antique shops to award-wining restaurants, scenic Appalachian Trail hikes, and beyond, Northwest Connecticut has something to offer everyone. Beyond Litchfield County, the Hudson Valley and Berkshires are a short drive from the cottage.

    Explore the Area

  • HOTCHKISS SCHOOL

    Just 10 minutes from Hotchkiss School campus, Pennybrook Cottage is a serene home base for families visiting Hotchkiss. Whether you're touring with a prospective student or attending a graduation or reunion, it’s the perfect spot to unwind after a full day on campus.

  • LIME ROCK PARK

    Stay close to the action—Lime Rock Park is just a short drive away. From vintage race weekends to world-class motorsport events like the new NASCAR LiUNA 150, it’s a must-see for car lovers and thrill seekers alike.

  • CULTURAL & SEASONAL ATTRACTIONS

    From the Garden Conservancy Open Days in May to Litchfield Jazz Festival in August to Jumpfest ski jumping in winter, the area is full of can’t-miss seasonal events that draw visitors from across New England.

  • NATURE & SCENERY

    From the waterfall trails at Kent Falls to scenic hikes along the Appalachian Trail, the area is rich with outdoor beauty. Paddle the Housatonic River, wander through White Memorial Conservation Center, or catch a sunset over Lake Waramaug.

  • GREAT BARRINGTON & THE BERKSHIRES

    Just 30 minutes north, Great Barrington offers indie shops, farm-to-table dining, and a vibrant arts scene. A bit further, Lenox is home to Tanglewood, a stunning open-air venue for classical, jazz, and popular music performances.

  • THE HUDSON VALLEY

    Just across the state line, the Hudson Valley is packed with charming river towns, antique shops, and scenic wineries. From Hudson to Rhinebeck, it’s an easy day trip for design lovers, foodies, and anyone chasing a perfect fall drive.

  • A cozy kitchen with cream-colored cabinets, wooden countertops, a stainless steel sink, and a stainless steel stove with a chimney hood. There are two windows with light-colored curtains, and a glass door with wooden framing leading outside. Decor includes a vase of yellow tulips and some cutting boards.
  • Cozy living room with wooden coffee table, vase with flowers, books, and a lit candle, sofa with decorative pillows, window with natural light, and framed pictures on the wall.
  • Living room with beige sofas, decorative pillows, a coffee table with books and a flower vase, a lit candle, and a wooden bookshelf in the background.
  • A cozy bedroom with a neatly made bed, beige headboard, dark patterned pillow, white pillows, and a beige quilt, with natural light coming in through wooden-framed windows, and a wooden dresser with a lamp and vase of flowers.
  • Living room with a brown high-back chair, a round coffee table with books and a vase of flowers, a dark TV stand with a mounted TV, and a brick fireplace with a mirror above it.
  • Outdoor patio dining area with wooden table, chairs, a large white patio umbrella, a vase of yellow tulips, stacked plates, and glasses in front of a white house with glass-paneled doors.
  • Bathroom with black wallpaper featuring a beige floral pattern, white pedestal sink, large black-framed mirror, chrome faucet, a bottle of soap or lotion, a small vase with flowers, a towel hanging on a wall hook, and a window with cream and black striped curtains.
  • A cozy dining room with wooden paneling, a rectangular wooden table with a gray tablecloth, and six wooden chairs. There is a glass vase with green foliage on the table. Large windows with blinds let in natural light. A small black sideboard with a coffee station is against the wall, and a coffee machine and kettle are on top. The room has a rustic, inviting ambiance.

  • “The Pennybrook Cottage is hands down the best Air BnB we have ever stayed in! The design, high quality furnishings and attention to detail is simply unmatched! If we could move in, we would. The location is beyond charming. Just steps from walkable Main Street and the trails! Highly recommend! We will be back very soon!”

    Renée

  • “The owners of this home have lovingly considered everything for their guests. From check-in to check -out our 3 day visit was magical. The location of Falls Village was perfect as we longed for a quiet respite, and yet close enough to explore a busy Millerton and enjoy all it had to offer also. The kitchen was appointed with everything you could possibly need, comfortable and clean furniture throughout the house. Blankets, towels, sheets galore. Everything was so thoughtful. CLEAN & FRESH, my top priority. Every expectation was met. We will definitely be back very soon.”

    Lisa

  • “Shelby and Chris have created an exceptional stay: their beautifully restored northern-CT home is filled with furniture and details that honor the area’s history while feeling fresh and thoughtful. The touches—from cozy textiles to well-stocked essentials—made us feel instantly at home. Plus, it’s an easy hop to Kent and Lakeville, with a fantastic neighborhood restaurant just a block away. Highly recommended.”

    Preston