Kid-friendly vacation rentals in Lanesborough

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Top-rated kid-friendly rentals in Lanesborough

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Canaan

5.0 out of 5 average rating, 134 reviews

Country Cottage

Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.

Mar 16 – 23

ﺩ.ﺇ577 per night

Guest favorite

Cabin in Savoy

4.98 out of 5 average rating, 186 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.

Oct 9 – 16

ﺩ.ﺇ428 per night

Guest favorite

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.

Sep 5 – 12

ﺩ.ﺇ682 per night

Guest favorite

Condo in Hancock

4.83 out of 5 average rating, 131 reviews

Cozy Condo @ Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

May 28 – Jun 4

ﺩ.ﺇ605 per night

Superhost

Home in Dalton

4.88 out of 5 average rating, 113 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.

Feb 16 – 23

ﺩ.ﺇ338 per night

Guest favorite

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.

Nov 19 – 26

ﺩ.ﺇ355 per night

Guest favorite

Guest suite in Hancock

4.83 out of 5 average rating, 154 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.

Mar 7 – 14

ﺩ.ﺇ299 per night

Guest favorite

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.

Oct 21 – 28

ﺩ.ﺇ534 per night

Guest favorite

Apartment in Plainfield

4.97 out of 5 average rating, 238 reviews

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

Mar 5 – 12

ﺩ.ﺇ446 per night

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 281 reviews

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.

Sep 4 – 11

ﺩ.ﺇ547 per night

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 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.

Sep 7 – 14

ﺩ.ﺇ437 per night

Superhost

Cottage in Lanesborough

4.85 out of 5 average rating, 250 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.

Feb 22 – Mar 1

ﺩ.ﺇ1,025 per night