Vacation rentals in Pontoosuc Lake

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

4.97 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, 184 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.

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.

Guest suite in Pittsfield

4.9 out of 5 average rating, 68 reviews

Newly Renovated Red Door Annex

Private keypad entrance with parking. Large bedroom with full bathroom. The spacious room has a high-end queen bed and a small table for eating/working. Small frig, microwave, toaster oven, and pour-over coffee in a small nook outside the bedroom. Popcorn, oatmeal and yogurt are provided. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas.1 mile to Berkshire Medical Center. 20 minutes to Lenox. Outdoor sitting area to come this summer.

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.

Apartment in Lanesborough

4.89 out of 5 average rating, 126 reviews

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!

Superhost

Home in Dalton

4.89 out of 5 average rating, 144 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.

4.98 out of 5 average rating, 692 reviews

Cottage in Shaftsbury

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Pontoosuc Lake vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation 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!

Superhost

Apartment in Pittsfield

4.8 out of 5 average rating, 44 reviews

Newly Renovated, and Spacious great for family

KelRating, 5 stars2 months ago

Have stayed here before. Will stay again. Fits my needs and Shahs a great host

5 out of 5 average rating, 35 reviews

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

ChrisRating, 5 stars3 days ago

Fil & Ellie’s place was the perfect stay for our getaway. Their home is amazing. We were very impressed by the amenities, the cleanliness and attention to detail. This place has everything you’ll need for a great stay. The hosts were also very helpful in answering our questions and assisting us with check-in. I would highly recommend staying here if you have the chance.

5 out of 5 average rating, 9 reviews

Home in Lanesborough

Lakefront Home on Ponstoosuc Lake, The Berkshires

VictorRating, 5 stars3 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!

4.97 out of 5 average rating, 58 reviews

Cabin in Saugerties

Luxury A-Frame Cabin in the Woods with Sauna

YaaraRating, 5 stars1 week ago

The cabin is beautifully designed, with great taste and attention to every detail. It was one of the best experiences I can remember – quiet, thoughtful, and simply perfect. Everything felt carefully considered, and Nicholas was highly responsive communicative, kind, and easy to reach. Thank you so much!

4.75 out of 5 average rating, 20 reviews

Pebbled Beach Cottage

AmandaRating, 5 stars5 days ago

The cottage is very cute and cozy with decent views of the lake. We enjoyed the couple of nights that we stayed and will definitely book again