Kid-friendly vacation rentals in Hancock

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Popular amenities for Hancock kid-friendly rentals

Kid-friendly house rentals

Top guest favorite
A historic white house is surrounded by lush green grass and trees. The two-story structure features a covered porch on one side, with large windows reflecting the natural light. Scenic hills are visible in the background, adding to the serene countryside setting.
Home in Dalton
4.99 out of 5 average rating, 155 reviews

Cleveland House - renovated Berkshires' gem.

MasonRating, 5 stars1 week ago
We had a wonderful stay at this beautiful home. The beds were extremely comfortable, the house was clean and the kitchen was well stocked. The hosts were very responsive and kind and went above and beyond to make sure we had a great stay. The kids in our group were happy with the toys that were available for them. We would highly recommend staying here for group gatherings. We had a lovely cozy weekend and are so grateful to the hosts!
Guest favorite
An open kitchen and dining area feature a wooden dining table surrounded by black chairs. The space is illuminated by natural light from large windows, with a breakfast bar visible in the background. A neutral color palette adds warmth to the inviting layout.
Home in Pittsfield
4.93 out of 5 average rating, 101 reviews

Net Zero home with rustic Berkshire charm

SarahRating, 5 stars4 weeks ago
We had a great stay. Easy to check in, home had everything needed to be comfy and cook a meal. Comfortable for 3 adults. Host is very friendly and accessible!
Guest favorite
A snow-covered landscape is visible, with trees lining the sides of a roadway. The hills in the background are partially obscured by clouds, suggesting a serene winter atmosphere. Several homes and parked cars can be seen along the road.
Home in Hancock
4.95 out of 5 average rating, 22 reviews

Condo on the mountain

NicholasRating, 5 stars5 months ago
Lovely one night stay! Perfect location on the mountain, super clean and Zaighum was very helpful and accommodating with an early check in. Would highly recommend!
Top guest favorite
A spacious white two-story house is set against a backdrop of lush greenery. The yard is framed by trees, featuring a patio area with seating and flags. A gravel driveway leads to the home, which offers a welcoming view of the outdoor space.
Home in Hancock
4.97 out of 5 average rating, 35 reviews

Berkshire Retreat: Huge Home W/Hot Tub & Yard

KaylaRating, 5 stars3 months ago
John was the best host! He was super responsive and the photos/ description were spot on! Had a great weekend there and only a 4 minute drive to Jiminey Peak! Definitely will stay again!
Top guest favorite
A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.
Home in Pittsfield
4.95 out of 5 average rating, 172 reviews

Cantabile life in the Berkshires

CrystalRating, 5 stars1 week ago
This was a great cute quiet place that fit our family perfectly. The gaming area was perfect and entertaining. My youngest daughter absolutely loved the piano! The host was very responsive and accommodating for sure. We would highly recommend 🥰
Superhost
A rustic red barn stands among lush greenery, featuring large glass doors inviting natural light inside. The path leading to the barn is lined with gravel, and a stack of wood is neatly arranged beside the structure.
Home in Cheshire
4.85 out of 5 average rating, 214 reviews

19th c. Barn in The Berkshires

JohnRating, 5 stars6 months ago
Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.
Guest favorite
An organically shaped mini-house is surrounded by lush greenery, with a stone pathway leading to a softly lit entrance. The structure features unique, curvaceous walls and several windows, harmoniously blending with the natural landscape of trees and foliage.
Home in Pownal
4.98 out of 5 average rating, 252 reviews

Cozy Vermont mini-house

DanielRating, 5 stars2 weeks ago
I had a wonderful stay at this charming mushroom home in Pownal! The space was incredibly cozy, making it perfect for a peaceful getaway. Everything was thoughtfully designed, which made it easy to relax and feel at home. One of the highlights, in addition to the house, was the beautiful yard, which turned out to be a birdwatcher’s dream. I spent hours outside enjoying the fresh air and spotting all kinds of birds; it truly felt like a nature retreat.
Guest favorite
Aerial view of the property reveals a spacious house surrounded by lush greenery and rolling hills. A winding path leads to the home, and various trees provide shade in the yard. The vibrant landscape showcases a blend of rich greens under a clear sky.
Home in Lanesborough
4.96 out of 5 average rating, 101 reviews

Berkshire Bliss- 6BR/Minutes from Jiminy +38 acres

ElenaRating, 5 stars3 months ago
We stayed at Jonathan’s place with 3 families, 6 adults and 7 kids ranging in ages from 4-10. It couldn’t have fit our families more perfect. The room setup is amazing, especially when renting with kids. When having that many rooms it’s usually one in a basement which wasn’t the case! We skied all weekend at Jimny peak and it was a short 8 minute drive to the mountain. Very spacious with a cozy living space for the kids to play and a great bonus room downstairs. Kitchen had everything we needed to cook meals. They also supply lots of games, kids loved that. Thanks for a wonderful weekend will be renting again next ski season!

Kid-friendly apartment rentals

Guest favorite
A bright living area is highlighted by a slanted ceiling and a pellet stove, offering warmth and comfort. Two black chairs are positioned on a patterned rug, while a sectional sofa provides spacious seating. Natural light filters through a skylight and window adorned with light curtains.
Apartment in Plainfield
4.97 out of 5 average rating, 271 reviews

Sunny, light filled loft in 1873 Colonial

DouglasRating, 5 stars1 week ago
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.
Guest favorite
A bright living space features large windows, allowing natural light to fill the room. A comfortable sofa sits beside a wooden coffee table, with visible mountain views outside. A round dining table is surrounded by wooden chairs, enhancing the room's spacious feel.
Apartment in Shelburne Falls
4.91 out of 5 average rating, 239 reviews

Soaring 2-level loft w/ views in heart of downtown

EssieRating, 5 stars4 days ago
The loft is perfectly located, bright & comfortable with the sound of the falls close by. Sue & Wendy are wonderful, responsive hosts who left generous welcome treats! I'm a repeat guest and will surely be back again.
Guest favorite
A charming entrance to the garden apartment is presented, featuring a black door flanked by windows and adorned with flower boxes. A set of black wrought-iron stairs leads to the entrance, while a flower planter with vibrant blooms adds color to the pathway.
Apartment in Center Square
4.95 out of 5 average rating, 130 reviews

Empire Plaza Apartment

TessaRating, 5 stars2 days ago
Great location, walkable to many restaurants, clear check in instructions
Superhost
A wooden dresser top displays a small white decorative house figurine alongside a potted green plant in a metallic pot. The background features white walls, emphasizing the simplicity of the decor.
Apartment in Troy
4.87 out of 5 average rating, 140 reviews

The Eastsider (Emma Willard, RPI, Troy)

KaiRating, 5 stars2 months ago
The studio apartment was just what I needed. The kitchen was outfitted with appliances, cookware, and dishes. The bed was comfy. John and Shauna were extremely responsive. A great spot for able bodied folks who need a nice little spot to lay their head while in town.
Superhost
An airy interior showcases exposed wooden beams and a blend of modern and rustic decor. A kitchen counter with stools is positioned towards the left, complemented by a dining table with chairs in the center. A cozy bedroom is visible through the doorway on the right.
Apartment in Philmont
4.9 out of 5 average rating, 118 reviews

Beautiful space in the heart of Philmont

JessicaRating, 5 stars7 months ago
Wonderful stay! Beautiful home and so much to do in the area. We had a great time!
Top guest favorite
A wide expanse of green grass is framed by a line of trees under a blue sky dotted with fluffy white clouds. The landscape conveys a sense of open space and tranquility, characteristic of the surrounding rural setting.
Apartment in Plainfield
4.95 out of 5 average rating, 269 reviews

Sunny carriage house apartment

JessieRating, 5 stars2 months ago
My partner had a lovely little getaway in Plainfield here. Very private, beautiful nature abound, quiet, and peaceful. Really close to a local co-op which had great food as well!
Guest favorite
A cozy living area features a light grey sofa paired with a wooden coffee table. An accent chair with a textured throw sits beside a basket. A large cow print hangs on the wall, with two framed pieces nearby. A patterned rug covers the floor.
Apartment in Bennington
4.95 out of 5 average rating, 164 reviews

Cooper's Place

EmileeRating, 5 stars3 weeks ago
This is our second stay at Kim’s house. It is the perfect private spot, not too far from town or country. It’s a small space, good for 2 people!
Top guest favorite
A cozy seating area features a large, woven hanging chair with a white cushion and a bright green accent pillow. A textured pouf and a small side table complement the space, which is surrounded by large windows offering views of the mountains and natural light.
Apartment in Freehold
5 out of 5 average rating, 302 reviews

Mountain View Retreat~Sunny Hill Golf / Skiing

Chi-ShengRating, 5 stars1 week ago
Definitely a space with great level of thoughts and details makes you feel comfortable and relaxed. Surrounded by the nature, you can immerse yourself in the beautiful mountain view and bird chirps, very peaceful and tranquil. We saw deers walking by, rabbit hiding in bush from raining, and a little chipmunk busy around the house all the time. Thanks Katey for sharing her beautiful home and being a great host, super responsive and provides lots of useful information. We had an amazing time!

Kid-friendly condo rentals

Guest favorite
A spacious living area features two patterned sofas and a wooden coffee table, complemented by a textured area rug. A dining table is positioned nearby, with a large window allowing natural light to illuminate the room. Subtle artwork decorates the walls.
Condo in Dover
4.91 out of 5 average rating, 110 reviews

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim

MichaelRating, 5 stars2 months ago
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.
Guest favorite
A game room is illuminated by large windows, providing views of the greenery outside. A foosball table sits prominently, alongside a multi-sport game featuring a basketball hoop and a net for volleyball. The space encourages active play with a modern and inviting setup.
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars1 month ago
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.
Top guest favorite
A modern living room corner features a brown leather recliner with high backrest beside a window. A small table holds a potted plant, while a wood stack is positioned against the wall for a rustic touch. Natural light filters through brown curtains.
Condo in Dover
4.99 out of 5 average rating, 120 reviews

Summer Dream! The Handle Lodge at Snowtree Condos

MarkRating, 5 stars2 months ago
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.
Top guest favorite
A welcoming living area features a comfortable seating arrangement with a gray armchair and decorative pillows. A modern electric fireplace is positioned beneath a wall-mounted television, adding a cozy touch. The open kitchen and dining area are visible in the background, creating a spacious atmosphere.
Condo in Saratoga Springs
4.98 out of 5 average rating, 125 reviews

Ideal location! Steps to Belmont and Broadway!

BrianRating, 5 stars3 months ago
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)!
Guest favorite
A bright living area features vaulted ceilings with large skylights. A comfortable gray sofa and a cozy red chair provide seating, while a wooden coffee table rests on a decorative rug. The space is filled with natural light and offers a view through arched windows.
Condo in Saratoga Springs
4.96 out of 5 average rating, 181 reviews

Owl's Nest - Unique Condo in Vintage Location

HeatherRating, 5 stars1 week ago
Cute space. Parking Space provided which was close to the door. Plush bathroom towels and nice bedroom linens. The place was nice and clean and had everything we needed. One block to the park and another block to the downtown area with lots to do! We had a wonderful visit and would rent again.
Guest favorite
A spacious living area is adorned with a large area rug and a comfortable blue bed. Large windows allow natural light to illuminate the room, highlighting the warm yellow walls and the vintage chandelier. A small coffee table and plush seating invite relaxation.
Condo in Center Square
4.9 out of 5 average rating, 266 reviews

Elegant, spacious studio apt in historic mansion

LindseyRating, 5 stars1 week ago
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!
Guest favorite
A comfortable living area showcases a gas fireplace beneath a large television mounted on the wall. A dark sofa sits beside a small coffee table, and light flows in through a glass door, which is accented by sheer curtains. Decorative elements enhance the space.
Condo in Dover
4.84 out of 5 average rating, 119 reviews

Walk to Mt. Snow-Spa-Summer Pool

GaryRating, 5 stars2 months ago
Great little studio spot to use as your Basecamp for activities in the area!
Superhost
Icicles hang from a structure in the foreground, with a view of snow-covered ski slopes illuminated by soft lights in the distance. The landscape is blanketed in fresh snow, creating a serene winter atmosphere.
Condo in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars15 months ago
We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!

Quick stats about vacation rentals that are kid-friendly in Hancock

  • Total rentals

    70 properties

  • Nightly prices starting at

    G$18,884 GYD before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    40 properties have a pool

Destinations to explore

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  3. Massachusetts
  4. Berkshire County
  5. Hancock
  6. Kid-friendly rentals