Holiday houses in Canaan

4.87 out of 5 average rating, 15 reviews

Spacious Queechy Lake House with Private Dock

Newly renovated, this lakefront home on Queechy Lake in Upstate New York is fully equipped for lakeside fun! We are also close to many ski resorts. Perfect for couples and families looking to take advantage of direct water access for a fun day on the lake. The 4-bedroom post and beam style house features a new wrap around deck to enjoy everything from grilling to beautiful evening sunsets. Enjoy lawn games, the fire pit and your own private dock. Comfortably furnished, you'll feel right at home!

4.93 out of 5 average rating, 184 reviews

Guest suite in Richmond

Tanglewood/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!

5 out of 5 average rating, 36 reviews

Barn in East Chatham

The Loft at Sweet Pea Farms

The Loft at Sweet Pea Farms is a modern, beautifully appointed apartment with every amenity you could need. Overlooking 140-acres of awe-inspiring farmland, the Loft boasts a huge 1500 sq ft space with one queen bedroom and an additional queen murphy bed in the living area. Enjoy a coffee while taking in views of rolling hills; listen to records while you sip a whisky; or make dinner for your friends & family. Work, unplug, or a little of both in this slice of heaven in the upper Hudson Valley.

4.91 out of 5 average rating, 130 reviews

Cabin in Chatham

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House is surrounded by acres of forest and is close to conservation areas with hiking trails. Minutes to antiquing, Kripalu, Norman Rockwell Museum, The Mount, Tanglewood, Skiing, Shakespeare & Co. You’ll love my place because of the peace, quiet and seclusion. Located up an old dirt country road. Relax by the wood stove (bring wood), in the sun room or explore nearby Spencertown, Chatham or West Stockbridge. Many ski slopes nearby & a small lake! If visiting in winter, 4wd recommended.

4.88 out of 5 average rating, 185 reviews

Apartment in Petersburgh

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

5 out of 5 average rating, 66 reviews

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Welcome to our little slice of heaven upstate. Located just a 5-minute drive to the MA border, a stay at our home in Canaan, NY means access to the best of both Columbia County and the Berkshires. In the summer, enjoy the private Adams Point Beach on Queechy Lake and easy access to Tanglewood. In the winter, explore 4 different local ski resorts and curl up by the cozy wood stove. In between, enjoy the peaceful pond views and secluded location on a dirt road. We can't wait to welcome you!

4.91 out of 5 average rating, 165 reviews

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.

4.99 out of 5 average rating, 253 reviews

Cabin in Canaan

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.

4.95 out of 5 average rating, 192 reviews

Cottage in New Lebanon

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 table.

4.99 out of 5 average rating, 219 reviews

Farm stay in Pittsfield

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.

4.96 out of 5 average rating, 55 reviews

Private Retreat: Hot Tub! Movie Room! Pool Table!

SUMMER: Stay includes: Access to Queechy Lake’s private beach. Sprawl out in this charming home that’s both private and close to everything! Discover everything this ALL SEASON Berkshires/Hudson Valley home has to offer. From skiing to Tanglewood, local farms to wineries, you’re close to it all! Relax in the hot tub lakeside while watching the beavers, curl up by the wood-burning stove, or play a game of pool. You’ll never want to leave!

4.97 out of 5 average rating, 131 reviews

Cabin in Chatham

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.

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Other great holiday rentals in Canaan

5 out of 5 average rating, 12 reviews

Chalet in Canaan

SRC-Hudson Valley/Berkshires Cultural Corridor

CariRating, 5 stars5 months ago

If you're thinking about booking Kristen's Chalet - do not hesitate! Book it - you won't be disappointed. The house has ample room to spread out with your family. We enjoyed our Christmas dinner at the dining table and afterwards, we were able to watch a movie together. The location was perfect for us to go out every day and explore - Red Lion Inn, The Mount and several other towns. We had to make plans to stay in so we could enjoy the beautiful Chalet for an evening. We can not wait to return and enjoy this beautiful home. ♡

4.95 out of 5 average rating, 225 reviews

Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

JenniferRating, 5 stars1 month ago

The space was beautiful, clean, and exactly as pictured! We enjoyed a weekend away and appreciated the local recommendations shared in the guide. We spent time exploring the farm, the surrounding area, and also were able to kick back and relax in the amazing property.

4.9 out of 5 average rating, 136 reviews

Cottage in Canaan

Plan your Berkshires by the lake

PattyRating, 5 stars3 weeks ago

I cannot emphasize enough how responsive, helpful and accommodating Julie was before and during our stay. The property is as shown, interior was clean and beds very comfortable. The walk to the lake is a short, peaceful one. It is a lovely setting with quiet neighbors. Highly recommend for anyone visiting nearby Berkshire attractions or for a quiet getaway near a beautiful lake!

Superhost

Tiny home in Chatham

5 out of 5 average rating, 3 reviews

Romantic-Private-Western Tiny Cabin + hot tub

DanielRating, 5 stars2 weeks ago

Heidi and Arthur truly curate a wonderful space. The outdoor space is lively and functional. There are plenty of places to sit, an outdoor shower, and of course the (very clean) hot tub. It is private and even has a wooden gate to enhance that feeling of peaceful seclusion. The inside is a nice mixture of cozy and chic. It goes without saying that everything is clean and accessible as well. They cover so many of the little things (coffee, razor, condiments, even microwave popcorn!) and it was such a nice surprise to even explore the miniature home. The decorations are extremely thoughtful, very charming, and high quality. We had a great time just taking pictures with the decor! The surrounding area is walkable and soo many great eateries are nearby (especially for brunch/breakfast or local pub/breweries). There are many hiking trails nearby and I cannot recommend the High Top Falls enough. Heidi is so proactive with recommendations and ensures your stay is perfect, unique, and magical!

4.99 out of 5 average rating, 68 reviews

Cabin in Hannacroix

A-Frame Log Cabin: Hot tub, views, & EV2 charger!

MinetteRating, 5 stars1 week ago

Really enjoyed our stay! Was perfect for our family to stay all in one place. Darin responded in a timely manner and was very helpful. Pool table was a great addition! Loved the location, it was beautiful & peaceful. We were disappointed we didn't see any bears :0) LOL

4.93 out of 5 average rating, 88 reviews

Cottage in Austerlitz

Harvey Mountain Lodge by State Forest

LauraRating, 5 stars1 week ago

Lisa’s place was wonderful, and I highly recommend it. She was very responsive to questions, and I appreciated the helpful notes around the house. The space was thoughtfully made dog-friendly, with couch covers that kept things worry-free. The garden was beautiful, and the property offered great outdoor spaces—a back deck, a front grill with seating, and a creekside trail (not fully cleared, but enjoyable). My dog and I loved it. We stayed on the top floor and loved the airy living room with high ceilings and skylights. Lisa’s nature-inspired decor on the desk and fireplace mantle added charm. The bedroom was spacious, and the extra-large bed was incredibly comfortable. The house having three bathrooms was a nice bonus.

4.93 out of 5 average rating, 28 reviews

Guesthouse in Chatham

Tranquil Guest House, Chatham NY

MikeRating, 5 stars3 weeks ago

We had a wonderful stay at Lucy's place. The house was clean, comfortable, modern and had everything we needed. Our kids loved running around the grounds and exploring the nearby stream. Very easy access into Chatham and the surrounding town. Lucy and her husband Sean (and their dog Timber) were super friendly and hospitable. We'd definitely stay there again!