Family-friendly vacation rentals in Lanesborough

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Top-rated family-friendly rentals in Lanesborough

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Guest favorite

Apartment in Shelburne Falls

4.98 out of 5 average rating, 488 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a newly renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Feb 20 – 27

G$20,441 GYD 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 12 – 19

G$37,807 GYD 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.

Jun 5 – 12

G$33,679 GYD per night

Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 258 reviews

Country Cabin

Lovely private country setting. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of the request.) The space is for 2 adults but I allow for flexibility, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

Oct 12 – 19

G$25,418 GYD per night

Guest favorite

Guest suite in Valatie

4.98 out of 5 average rating, 231 reviews

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

Sep 7 – 14

G$19,054 GYD 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!

Oct 9 – 16

G$24,852 GYD per night

Guest favorite

Farm stay in New Ashford

4.9 out of 5 average rating, 221 reviews

Sheep Barn on the Greylock Valley Estate

Located 10 minutes from Williamstown, the Sheep Barn is a completely renovated antique barn, with 3 bedrooms, 2 full baths, and full kitchen. It's the perfect place for spring and summer getaways, cozy fall weekends, and winter ski vacations. Offering hiking trails and complete privacy, it is still close to Williams College, Jiminy Peak, and other Northern Berkshire attractions. During winter months we recommend that guests have All Wheel Drive vehicles.

Feb 28 – Mar 7

G$35,691 GYD per night

Guest favorite

Barn in Williamstown

4.97 out of 5 average rating, 261 reviews

Cozy barn apartment on the river

Private converted first floor barn apartment in a New England home next to the Green River. Comfortable with unique furnishings and back door to river patio. Sleeps 1-2 comfortably. Can accommodate 4 with the extra sleeper tri-fold mattress, (Best for 1-2 smaller children). Private full bath. Great for 1-2 adults or a family with smaller children. Due to Coronavirus we are doing extensive disinfecting and allowing for 72 hours between bookings.

Aug 10 – 17

G$29,381 GYD 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.

Mar 18 – 25

G$57,062 GYD per night

Guest favorite

Apartment in Plainfield

4.95 out of 5 average rating, 237 reviews

Sunny carriage house apartment

Our sunny apartment is located midway between Northampton and the Berkshires, in a lovely rural setting. The kitchen, bath and studio living area are in a private apartment, surrounded by 12 acres of open fields. The kitchen is well equipped and includes all the makings for tea and coffee. Orange juice, oatmeal, English muffins and homemade granola are also provided!

Sep 28 – Oct 5

G$23,412 GYD per night

Guest favorite

Apartment in Bennington

4.93 out of 5 average rating, 529 reviews

The Octopus's Garden

Welcome to the Octopus' Garden, a warm and cozy oasis located in the heart of Bennington, VT. This relaxing one bedroom suite, infused with amenities and much love, comfortably accommodates 2 people. This peaceful space is only a 10 minute walk to art, shops and dining and is the perfect hub for a variety of activities in Southern Vermont and Western Massachusetts.

Oct 15 – 22

G$20,348 GYD per night

Guest favorite

Loft in East Nassau

4.99 out of 5 average rating, 154 reviews

Dog Friendly Farm Spring bird watching

Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!

Sep 13 – 20

G$33,407 GYD per night