Holiday rentals in Lanesborough

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Top-rated holiday rentals in Lanesborough

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Guest favourite

Cabin in Savoy

4.98 out of 5 average rating, 188 reviews

The Camp - 20 Minutes to Berkshire East!

Enjoy the peaceful silence, private forested expanses, wildlife, and unforgettable starry night skies from this wonderful home. Only 8 minutes to the village of Charlemont and 5 to the Tannery Falls entrance of the Savoy State Forest. During your escape on the mountain rest assured that you’re only a 30 minute drive to Norths Adams, Greenfield. Highlight your visit with journeys to Berkshire East Ski Resort, Thunder Mountain Biking, Zoar Outdoor River Rafting, MASS MoCA, or the Clark Art Museum.

31 Aug – 7 Sep

₹9,523 per night

Guest favourite

Cottage in Lanesborough

4.93 out of 5 average rating, 220 reviews

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.

21–28 Sep

₹15,150 per night

Guest favourite

Flat in Lanesborough

5.0 out of 5 average rating, 22 reviews

Cozy Berkshire Waterfront Home

Welcome to our charming waterfront home on Pontoosuc Lake! The Berkshire Lakescape is perfect for a romantic getaway for a couple or two, or a solo adventure away. Soak in lake views from the deck or try to catch a stunning sunset from the water’s edge. Kayak straight from our backyard and return for marshmallows at the firepit. Explore Berkshires' culture and outdoor activities - Tanglewood, Mount Greylock, and more are just a short drive away. We can't wait to host you for a memorable stay.

15–22 May

₹13,261 per night

Superhost

Home in Dalton

4.88 out of 5 average rating, 114 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.

15–22 Sep

₹9,818 per night

Guest favourite

Flat in Pittsfield

4.96 out of 5 average rating, 49 reviews

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!

18–25 Jan

₹10,801 per night

Guest favourite

Guest suite in Williamstown

4.96 out of 5 average rating, 202 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

25 Dec – 1 Jan

₹8,415 per night

Guest favourite

Guest suite in Hancock

4.83 out of 5 average rating, 155 reviews

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

5–12 Apr

₹7,566 per night

Superhost

Flat in Lanesborough

4.86 out of 5 average rating, 64 reviews

Charming Apt. in 18th c. Berkshire Farmhouse

This lovely 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 cute apartments. 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. *Check out our other rentals on our profile!* Follow us on IG @SecondDropFarm

24 Apr – 1 May

₹8,964 per night

Guest favourite

Cabin in Cheshire

4.89 out of 5 average rating, 152 reviews

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.

18–25 Jan

₹11,887 per night

Guest favourite

Flat in Pittsfield

4.92 out of 5 average rating, 26 reviews

Comfortable Pittsfield Loft

Located in the center of the Berkshires, this newly renovated Pittsfield apartment is comfortable and convenient. Come enjoy the new kitchen and delightful walk in shower. Centrally located to all of the wonderful Berkshires attractions this one bedroom apartment offers new appliances, driveway parking, washer and dryer. Yuhong and Mike live on-site in the apartment below and they are dedicated to providing an excellent guest experience. THIS IS A NO SMOKING APARTMENT

12–19 May

₹6,264 per night

Guest favourite

Farm stay in Pittsfield

4.99 out of 5 average rating, 107 reviews

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 take a walk on our hiking trail.

5–12 Sep

₹9,724 per night

Superhost

Cottage in Lanesborough

4.85 out of 5 average rating, 251 reviews

Wildlife Lakeside Cottage

Fully furnished , totally remodeled ( completed in Feb. 2016), private cottage 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. For conditions message Jill.

12–19 Apr

₹22,808 per night