Holiday rentals in Lake Onota

4.86 out of 5 average rating, 290 reviews

Cabin in Stephentown

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

4.94 out of 5 average rating, 416 reviews

Chalet in Otis

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

4.93 out of 5 average rating, 102 reviews

Home in Pittsfield

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

4.88 out of 5 average rating, 184 reviews

Flat 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.

4.92 out of 5 average rating, 24 reviews

Home in Pittsfield

The Guest House at Cottage Farm

The Guest House at Cottage Farm blends the warmth of home with the elegance of a luxury retreat. Nestled in the picturesque heart of the Berkshires, this beautifully restored 2,300 sq foot haven has been thoughtfully designed, offering a serene escape for week-long getaways and weekend retreats. Whether you're planning your dream wedding weekend or seeking to immerse yourself in the Berkshires' culture and natural beauty, Cottage Farm invites you to unwind and create unforgettable memories.

4.98 out of 5 average rating, 213 reviews

Cabin in Cummington

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

4.95 out of 5 average rating, 174 reviews

Home in Pittsfield

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

4.89 out of 5 average rating, 144 reviews

Home in Dalton

The Yellow House

The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.

4.95 out of 5 average rating, 191 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, 218 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.

4.93 out of 5 average rating, 375 reviews

Guest house in Lenox

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

4.9 out of 5 average rating, 126 reviews

Yurt in Stephentown

Off Grid Yurt Right By The Best of The Berkshires

This is an off grid yurt with a woodstove for heat and an off grid kitchen - no running water or electricity - water can be heated on the woodstove. You'll have a comfy bed and futon. We love it when it rains. Staying inside, listening to the rain on the yurt and playing games is a highlight of our trips there. Cooking outside and enjoying a campfire & toasting marshmallows is also fun!

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Other great holiday rentals in Lake Onota

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.

4.96 out of 5 average rating, 24 reviews

Cabin in Stockbridge

Stockbridge Snug- cabin luxury just steps to lake!

MichaelRating, 5 stars1 week ago

The Snug was exactly what we were looking for! A beautiful house on an amazing piece of property in a fantastic location for exploring the Berkshires. The entire environment was so peaceful and serene. On the inside the house was clean, comfortable, inviting and had everything we needed. The floor to ceiling windows looking out into the wooded back yard were one of our favorite features of the house. On our last day of our stay we were lucky enough to see a family of deer make their way through the back yard. The wood fired hot tub was magical and well worth the wait to heat up. The hosts were informative, responsive, helpful and very nice. They genuinely cared about our stay. Thank you McCaela and Joe for sharing your lovely house with us, we can't wait to come back!

4.96 out of 5 average rating, 54 reviews

Home in Canaan

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

MusserRating, 5 stars1 week ago

This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.

4.91 out of 5 average rating, 45 reviews

Flat in Pittsfield

Comfortable Pittsfield Loft

ThomasRating, 5 stars3 weeks ago

I had simply the best time--the nicest people, a beautiful apartment, an absurdly good value, and a great location for exploring western Mass. I'm looking forward to staying here again next time I'm in this part of the country. Do yourself the favor and choose this one, you won't be disappointed.

5 out of 5 average rating, 10 reviews

Flat in Hancock

Artsy loft near MassMoCA with pool and hot tubs

NicoleRating, 5 stars2 months ago

We had a great stay at the end of ski season; the place was quiet and relaxing. We will definitely return!

5 out of 5 average rating, 41 reviews

Flat in Lanesborough

Cozy Berkshire Waterfront Home

MarkRating, 5 stars3 months ago

Can’t say enough good things about this find near Jiminy Peak in the Berkshires! Stayed for three nights while skiing two days over presidents weekend. Hosts were very thoughtful and flexible. Left cookies and s’mores kit which were a nice touch. During snowstorm steps to the unit and walking areas were kept shoveled and salted. For us and our two teenagers this offered the perfect alternative to pricey on mountain lodging and was only about a 13 minute drive. There was even a bonus game room which could probably serve as a small additional bedroom if someone had the need, it certainly has room for a twin air mattress. Our two kids shared the queen bed with minimal fighting, but that would’ve been our back up plan😂. Anyway, they were super responsive, check in and check out was easy and will certainly look to stay again if we get up there to ski again this year !

5 out of 5 average rating, 5 reviews

Cabin in Becket

WALK to lake! Dog friendly, A-Frame in Berkshires!

AustinRating, 5 stars1 week ago

What more could you want? This quaint cabin situated in the woods offers privacy, unique architecture, comfort, and peace. It’s equipped with everything you could possibly need, and the hosts were truly some of the most responsive and kind people I have ever interacted with. They truly went above and beyond for us. We stayed with a toddler and two dogs, and they all loved the property and the cabin. We will most definitely be back!