Holiday rentals in Pontoosuc Lake

4.97 out of 5 average rating, 117 reviews

Berkshire Lake- Modern and Updated-close to skiing

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

4.93 out of 5 average rating, 244 reviews

Cottage in Lanesborough

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

4.88 out of 5 average rating, 185 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.

4.96 out of 5 average rating, 55 reviews

Charming lake home with amazing sunset views

Keep it simple at this peaceful and centrally-located home with the best sunset lake views in every season . Fully furnished home overlooking Pontoosuc Lake. Upper and lower level decks with outdoor furniture and gas grill perfect for summer bbqs. The sunroom overlooking a 180 degree view of the entire lake is astounding and has a 55 inch tv and a gas fireplace, perfect for those cooler nights .Walking distance to lake access for swimming and boating. Minutes from hiking, biking and shopping.

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.

4.89 out of 5 average rating, 127 reviews

Flat in Lanesborough

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse

This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four separate cute suites. Newly updated kitchen, bathroom and furniture. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife. Follow us on IG @SecondDropFarm

4.95 out of 5 average rating, 174 reviews

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!

4.96 out of 5 average rating, 85 reviews

Flat in Pittsfield

The sweet place in the beautiful Berkshires!

Spectacular view of Pontoosuc Lake and mountains. During the warmer season, directly across the street, is Berkshire U-Drive Boat Rental. Rent a pontoon boat and sit back and relax and enjoy the view! Reserve now - bookings fill up quickly! There is ice fishing on this lake but be sure to have a Massachusetts fishing license! For snow skiing, Jiminy Peak Mountain Resort and Bousquet Mountain are approximately 12 minutes away! Tanglewood in Lenox, MA is approximately 20-25 minutes away!

Superhost

Home in Dalton

4.89 out of 5 average rating, 145 reviews

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.

4.89 out of 5 average rating, 164 reviews

Cabin in Cheshire

Private Paradise in the Berkshires

Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.

4.84 out of 5 average rating, 279 reviews

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. Sleeps 6. Ther are two full and one 1/2 baths.

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.

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Other great holiday rentals in Pontoosuc Lake

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.

Superhost

4.92 out of 5 average rating, 24 reviews

The Guest House at Cottage Farm

JaimeRating, 5 stars4 months ago

What a beautiful home! We loved it all-the home itself, the property, the scenery, the whole package. It is such a private property where you can truly appreciate the landscape & beauty of it all. It was close to the local ski area which my family enjoyed. I would absolutely stay here again & recommend it whole heartedly. Five stars from us!

4.88 out of 5 average rating, 32 reviews

Berkshire Lakehouse - 3 bedrooms - sleeps 5

JamesRating, 5 stars3 weeks ago

Wonderful place on the lake with a great host. Janice was very responsive, offered an early check-in and set up a baby gate. Great place for dogs and kids.

Guest house in Pittsfield

4.96 out of 5 average rating, 78 reviews

The Nest at Birdland

MichelleRating, 5 stars1 week ago

The Nest was a great spot for us to rest and recoup before our NEYC day! Mary was easy to work with, communicated well, and provided a great space with so many thoughtful extras!

5 out of 5 average rating, 11 reviews

Flat in Hancock

Artsy loft near MassMoCA with pool and hot tubs

GinaRating, 5 stars4 days ago

The absolute perfect location at the heart of the Berkshire Yoga Festival! Loved the location. Very comfortable for two people. The host was very quick to respond and was accommodating. I would definitely recommend and would stay there again.

4.91 out of 5 average rating, 76 reviews

Tiny home in Cambridge

A Bedroom in the woods with lovely views!

EricaRating, 5 stars1 month ago

Beautiful view! It was like we were one with nature🌲

5 out of 5 average rating, 10 reviews

Home in Lanesborough

Lakefront Home on Ponstoosuc Lake, The Berkshires

VictorRating, 5 stars4 months ago

Stephen’s home was the perfect place for two families to use a base for skiing at Jiminy and getting around the area. The home was as described, comfortable and plenty of space for all of us. Stephen was very responsive and accommodating during our stay. There was a lot of snow during the week we were there and he was in constant communication with us, to help us with anything needed. Thank you for the great stay, we would definitely stay here again!