Holiday rentals in Canaan

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

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!

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and ironwork table.

Berkshire Lakefront House with Amazing Views

Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

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.

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

The Hobbit House at June Farms

Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Scottish highland cows, Gloucestershire spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!

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.

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

Orchard House: 1850s Farmhouse- Hudson Valley

Welcome to our family’s beloved farmhouse — a warm, art-filled retreat tucked between the Hudson Valley and the Berkshires. Built in the 1850s and surrounded by 11 acres of gardens, orchards, and woodlands, this home is filled with stories, laughter, and character. It’s not just a place to stay — it’s a place to feel at home, to reconnect, and to make memories together.

Harvey Mountain Lodge by State Forest

Charming, fully equipped 2 1/2 bed/3 bath lodge at the end of a dirt road next to a babbling brook surrounded by 3000 acres of forest. Spend time enjoying the outdoors skiing, hiking, mountain biking, fishing, and creek walking. or exploring the Hudson Valley and the Berkshires. This is the perfect place to unplug and recharge!