Holiday rentals in Richmond

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

SKI Bousquet/Private Ranch/Kid&Pet Friendly/Horses

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail ride lessons /Horse activities available by appt!

Sunshine Cottage

Sunshine Cottage a peaceful place to rest and relax while being centrally- located to many of the attractions that make this area a beautiful place to visit. We are about 15 minutes away from Balderdash Winery, Hilltop Orchard/ Winery and Home Range Winery. Tanglewood, Berkshire Botanical Gardens, Jacobs Pillow, Red Lion Inn and Hancock Shaker Village bring culture and magnificent shows. You can ski at Bousquet Mountain, Ski Butternut and Jiminy Peak Mountain Resort. Come visit the Berkshires.

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Rustic Barn Studio Apartment

Built from a saved, moved, & reconstructed 1850s- era barn from a former local dairy farm, this upstairs studio space features views of the Berkshire Mountains and walking paths on the 5 acre grounds. 20 mins from Jiminy Peak. 20 mins from Tanglewood Music Center. The space has a queen bed, sofa, kitchen area with fridge, sink, oven, stove, microwave, Keurig and coffee, toaster, and cooking essentials. **EV Charging Station coming sometime summer of 2023. We'll update when available.

Bucolic Pet Friendly Oasis | 10 min to Tanglewood

Escape to our peaceful retreat on 5 private acres. Large picture windows envelope you in the gorgeous surroundings, and the tree lined property creates a sense of utter tranquility. Bask in the breeze on the sun porch, curl up by the wood burning stove, or enjoy a lounge on the deck. Centrally located in the Berkshires: ⭐️ 10 minutes to Tanglewood/Lenox ⭐️ 7 minutes from West Stockbridge/ I-90 ⭐️ 20 minutes to Great Barrington, Stockbridge & Pittsfield Enjoy our oasis all year r

Chic Cottage at Richmond Pond

Come enjoy all The Berkshires have to offer at our chic country cottage! Imagine relaxing by the cozy wood stove after a day spent exploring. With two bedrooms and a fresh bathroom, it’s perfect for a peaceful getaway. A short walk brings you to a private community beach on Richmond Pond, or enjoy music at nearby Tanglewood and winter skiing and tubing at Bousquet. Whether you’re here for relaxation or adventure, our inviting home is perfectly located to make your stay memorable.

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Newly Renovated Red Door Annex

Private keypad entrance with parking. Large bedroom, full bathroom. The spacious room features a queen bed and a small table for dining and working, a small frig, microwave, toaster oven, and pour-over coffee in a nook outside the bedroom. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas. 20 minutes to Lenox. Fire Pit. NEED MORE SPACE FOR CHRISTMAS WEEK? Check out Christmas in the Berkshires to rent the whole house.

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Richmond Ranch w/ Hot Tub by Evergreen Home

6 MINUTES TO BOUSQUET MOUNTAIN SKI AREA Charming 3-bedroom, 2-bath ranch in a quiet neighborhood. Enjoy one-level living with a sun-filled porch, deck, and hot tub for ultimate relaxation. The spacious basement offers a large open living area, perfect for gatherings. Walk to Bartlett's, and just minutes to Richmond Pond, Tanglewood, and only 13 minutes to Downtown Lenox. A beautifully decorated retreat for comfort and convenience in the Berkshires.

Main Street Delight One Bedroom Apartment

Located on Main Street in downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for four, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a Smart TV for relaxing. Wi-Fi is available throughout the space. Central heat and air to provide a comfortable environment in any season. All linens and towels are provided.