
Kid-friendly holiday rentals in Lanesborough
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Top-rated family-friendly rentals in Lanesborough
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Popular amenities for Lanesborough family-friendly rentals
Kid-friendly house rentals

Cleveland House - renovated Berkshires' gem.
We had a lovely stay at Elizabeth's place. The house was big enough for our large group, the kitchen was well stocked with anything we might need, and the area was peaceful and beautiful.

Whispering Woods Guest House
Taylor was an amazing host! Her home was super comfortable! We would absolutely stay again if we are in the area! Thank you for the amazing stay!

New Berkshire home - 3 bed, 2.5 bath w/views
2nd year staying there. Trina is great and as usual the house was perfect! we'll see you next year!

Berkshire Mountain House
This property was fantastic. It was great for adults and kids. The inground pool and hot tub were used all day and night. The house had many amenities for everyone. We have 3 grand children, (ages 5-7), the hosts had all kind of spaces and toys for them to utilize. Excellent place for kids inside and out! House was very well appointed and very user friendly. We loved our family time there and would not hesitate to return. Thank you!!!

Bougie B’s Mountainside Getaway
Absolutely beautiful space. Spotlessly clean. Full kitchen amenities plus a little coffee station. Fabulously comfortable beds and living room furniture. Deliciously soft towels. Just an overall great experience and peaceful stay!!

Cantabile life in the Berkshires
Jia place was great. Very spacious and plenty of things to do. It was very clean. The entire process was super simple. We enjoyed it quite a bit.

Brooksong, the perfect Berkshires getaway
Thank you, Salome, for a wonderful stay. Our extended family felt very relaxed and comfortable in your lovely home. It was a rainy weekend, so it was especially nice that there was a pool table, a fuzeball table, and lots of places in the house to hang out together. The bedrooms and bathrooms were lovely and the shared space was large and inviting. We enjoyed making meals together in the open kitchen. And the neighbor was so picturesque! We loved staying next door to the horses and donkeys, and taking walks on your beautiful farm-filled road. Thanks so much for making our stay such a special weekend. We all hope to ba back again! Very best to you and yours, Joanna and family

Charming lake home with amazing sunset views
My family and I had a great stay here. The property was well kept and matched the description. And the host was responsive and helpful. Would stay again if we're in the area.
Family-friendly apartment rentals

In town, newly renovated studio with private deck
Our experience at Carrie's studio apartment was just what we needed after a busy day attending to a family project. The apartment is spacious and nicely appointed with a comfortable bed, couches and lounging chair. The kitchen is well-equipped and the bathroom neat and clean. Although we didn't have much time to enjoy it, a small outside porch overlooking a lower garden and an expanse of a neighbor's green lawn was an added perk. The apartment is a short walk into the village of Shelburne Falls with its diverse shops, many eateries, pharmacy (good spot for an ice cream soda), small grocery store (an organic oriented store is just across the bridge), bookstore, and very nice wine store (near the Pot Holes). Don't miss Gypsy Apple, a culinary treat for a special occasion (check for the evenings open as they are limited). Our respite at Carrie's was peacefully quiet and restorative. I have no reservations about recommending Carrie's lodging.

Sunny, light filled loft in 1873 Colonial
Peter and the apartment were great! Peter was super responsive, friendly, and had nice touches like homemade granola with milk and coffee provided. After my original AirBNB fell through at check-in at 6pm, I was relieved (and saved) by Peter’s responsiveness.

full apartment in adams self check in
My sister and I are originally from the area. We were home for a family reunion. We were familiar with the area. This unit was simple, comfortable and adequate for our needs. Our hosts were quickly responsive. We would book here again when in the area.

West Main
Loved this little apartment. It has everything you need and more.

Historic Victorian - Entire 3rd floor
Our stay couldn’t have been better. The listing matched reality perfectly—stairs and all—and the hosts stayed a step ahead with friendly, detailed messages and a useful house guide. The location is superb: an easy stroll to everything in North Adams and a great jumping-off point for exploring the Berkshires. The home itself was spotless, cozy, and wonderfully quiet. The hosts were extremely understanding of a minor issue (our fault) that occurred. We thoroughly enjoyed our visit and would gladly return.

Empire Plaza Apartment
⭐️⭐️⭐️⭐️⭐️ A Hidden Gem in the Heart of Albany! From the moment we stepped through the door, this place felt like a cozy retreat tucked into the charm of New York’s capital. Immaculately clean, thoughtfully decorated, and stocked with everything we didn’t even know we needed. The location was ideal — just a short walk to Washington Park and a quick drive to all the historical spots. But the real standout? Our host. Incredibly responsive and warm. If you’re looking for a stay that blends comfort, style, and a true sense of place — this is it. Would give it six stars if I could!

The Eastsider (Emma Willard, RPI, Troy)
This was my second time staying here and it’s perfect what I needed. I come up from the city to work Saratoga racetrack and just need a place to lay my head. It’s great affordable and clean. If you’re interested in downtown Troy, it’s a quick 10 minute drive. Also there is a Stewart’s close by. John and Shauna were very accommodating on both my visits!

Sunny carriage house apartment
We had a great time at this lovely spot! Erin was a very kind and responsive host, and the apartment was just as described :)
Family-friendly apartment rentals

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim
We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.

Mt Snow Ski In/Out at Seasons
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

Summer Dream! The Handle Lodge at Snowtree Condos
Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

Ideal location! Steps to Track and Broadway!
Carla was a wonderful host. More importantly her rental was beautiful and very comfortable. Would strongly recommend and we look forward to going back (when there’s less snow)!

Owl's Nest - Unique Condo in Vintage Location
Stunning location a short walk through lovely Congress park to downtown Saratoga. Scrumptious bakery in easy walking distance. The apartment was delightful: very clean with all the essentials stocked. We loved being able to stop back in during the day for a quick recharge before getting back into the middle of everything. Bright and sunny during the day and quiet and peaceful at night.

Updated Ski in/Ski out Stratton Condo!
Caitlyn An excellent host quick to respond despite moving with her babies the same day as my trip! She was accommodating and provided a clear quick easy in from my late night travel. Her space is large and spacious with great set up lighting and comfortable and clean bedding. Loved the couch bedding set up! The entrance allowed ease to store the ski stuff so roomy keeping the living space free of the typical ski vacay clutter! The bathroom shower temp and pressure with soft towel and wash cloths provided with soap, and shampoo and conditioner gave a nice end of the day relax. Plenty of blankets for layering that may be needed. Kitchen appointed well with a good stove and oven easy to use and to easy prepare with pans and utensils for cooking, plenty of silver ware and plates glasses and plates that i truly appreciated. Couldn't use the ski in/ ski out as that lift was this late int eh season but how easy was it to scoot down in 2 min! Will be my stratton stay always onward!

Elegant, spacious studio apt in historic mansion
Such a unique stay! David gave very helpful instructions for arriving and getting to the property, even supplied photos for extra assistance. The property itself is cozy and in a great part of the city. There’s lots to do nearby, super walkable, and David provides great local recommendations. The shared gallery space was so cool to see too. Great experience!

Cozy & walking distance to cafés *spring avails*
Cozy apartment, walking distance from the water front. Had a great weekend getaway.
Quick stats about holiday rentals that are kid-friendly in Lanesborough
Total rentals
50 properties
Nightly prices starting at
$116 SGD before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
40 properties have a pool
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- Stratton Mountain
- Saratoga Race Course
- Six Flags New England
- John Boyd Thacher State Park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Zoom Flume
- Bash Bish Falls State Park
- Stratton Mountain Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Beartown State Forest
- Mohawk Mountain Ski Area
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- Hildene, The Lincoln Family Home
- Brignole Vineyards