Kid-friendly holiday rentals in The Berkshires

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for The Berkshires family-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Saratoga Springs
4.94 out of 5 average rating, 100 reviews

Private house, walking distance to downtown

SusanRating, 5 stars1 month ago
We had a wonderful 2-night stay in Saratoga Springs. Nikki was very responsive and promptly answered all questions. The house was exactly as described and was very clean and comfortable. It was in a great location in a quiet neighborhood which was a short walk into downtown. I highly recommend the house to anyone who wants to experience the great city of Saratoga Springs!
Guest favourite
Home in Athens
4.84 out of 5 average rating, 170 reviews

A Victorian "Lady"

RonaldRating, 5 stars5 months ago
Well kept clean old house and furnishings. Terrific unobstructed view of the Hudson from two of the bedrooms and living room facing East. I loved sitting by the bay window in the master bedroom with the sun shining in watching barges on the river and with views of the town of Hudson on the far side of the river. The owners stuff was in the closets and refrigerator and freezer full of her food but that did not bother me. I appreciate having condiments, salt, sugar and pepper available. There is a washer/dryer but no dishwasher and only one bathroom. Also no shades on the East facing window in the master bedroom so light streamed in at sunrise.
Guest favourite
Home in Phoenicia
4.96 out of 5 average rating, 154 reviews

Hiking and Breweries! Mountain and river views!

DallasRating, 5 stars1 week ago
This home was perfect in many ways. The home itself is bright with sunshine, has a beautifully-updated persona while keeping its mountain cabin charm. The kitchen was well supplied and we were able to cook meals easily. We also enjoyed the selection of books and games during the evening hours. If we still had young children around, they would have loved the fun kid's room upstairs! Plenty of available hiking nearby with a good selection of local restaurants for various libations and meals. Working with Julie was super easy - communications were quick and simple. No problems at all - a very excellent place for a relaxing holiday!
Top guest favourite
Home in Whitingham
5 out of 5 average rating, 57 reviews

2.5mi from the lake! Fire pit, arcade, yard games!

JuliaRating, 5 stars1 month ago
Great spot! Stayed at Eric's place for a weekend with a group of college students (8) looking to hit the reset button and had plenty of space. It was spotless and comfortable, and we had no trouble finding what we needed. The virtual guide is also super helpful!
Superhost
Home in Ulster Park
4.88 out of 5 average rating, 227 reviews

Entire lake house to yourself. Great for groups

Maggie FuentesRating, 5 stars1 week ago
Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!
Top guest favourite
Home in Cohoes
5 out of 5 average rating, 120 reviews

Cheerful, quiet 3 bedroom home

DonnaRating, 5 stars1 month ago
Our hosts were very easy to work with. I felt they cared about our visit and wanted to accommodate us in any way that would make her stay even more pleasurable. The house offered every convenience, including kitchen items for make-at-home meals. Thanks so much, Brandon and Brian!
Guest favourite
Home in Pine Plains
5 out of 5 average rating, 15 reviews

Stony Hill Haus in Pine Plains

StaceyRating, 5 stars6 days ago
My daughter and I spent a lovely weekend at Chelsey and Dominic’s house. It was the perfect place for reading, laughing and lots of conversation. Easy to get almost anywhere in Hudson Valley. We enjoyed walks around the property and seeing quite a lot of wildlife. The setting is truly magical.
Guest favourite
Home in Bloomfield
4.96 out of 5 average rating, 118 reviews

Spacious Charming New England Cape

JesseRating, 5 stars1 week ago
This is the second time time we've stayed at Carol's place. It's spacious, comfortable, with plenty of open rooms. The kitchen is extremely well stocked. This is becoming our yearly must-stay place!

Family-friendly apartment rentals

Superhost
Flat in West Brattleboro
4.76 out of 5 average rating, 131 reviews

Cute, Convenient with Big Backyard

MichaelRating, 5 stars3 months ago
Our stay was in the cold of winter and there was ample heating in the form of radiators spread about, extra blankets, and a very powerful space heater in the living room. The artwork, furniture and layout gave a comfortable and cozy feeling. I stayed with two friends and we cooked all our meals easily with what was provided in the kitchen as far as pots, pans and utensils. During our stay John was extremely responsive and accommodating over the air bnb messages. The house is older so outlets were oddly placed with only two prongs, most of the lights were hand pull to turn on and off, and the bedroom doors locked with a hook and latch. It all felt very clean and comfortable and we were very happy with our stay.
Superhost
Flat in Town of Rockingham
4.83 out of 5 average rating, 182 reviews

Apartment on Main Street

WinnieRating, 5 stars1 month ago
This was a very spacious and cozy spot! A perfect place for a quiet weekend getaway with proximity to hiking and/or skiing/snowboarding. There were many books, games, and puzzles available to peruse and enjoy as well.
Guest favourite
Flat in Hudson
4.9 out of 5 average rating, 167 reviews

Private 1BR Apartment 1 Block from Warren St.

JamieRating, 5 stars2 weeks ago
My daughter and I had plenty of space to spread out. John’s place is very comfortable, clean, and charming. Thoughtful touches like extra hooks, suitcase stand, and bench at the entry to take off our wet shoes after a rainy Spring day in Hudson. Easy walk to great coffee shop and restaurants. Would definitely return!
Top guest favourite
Flat in Cornwall-on-Hudson
4.98 out of 5 average rating, 214 reviews

Charming Efficiency

SaraRating, 5 stars2 weeks ago
I had a short, but lovely stay at Laurie's apartment. It is even more charming than the pictures show. I had a question for Laurie and she called me back as soon as she could. If I am up that way again, I would definitely stay again.
Guest favourite
Flat in Northampton
4.85 out of 5 average rating, 548 reviews

Parkside downtown cozy apartment

MicheleRating, 5 stars2 days ago
What a charming and peaceful home. It has everything you might need for comfort, cooking and relaxation including a well equipped kitchen, spacious rooms and beautiful setting. It’s close to everything but feels private. I would book again if I were in the area.
Superhost
Flat in Newburgh
4.83 out of 5 average rating, 304 reviews

Unwind in a Bespoke Downtown Studio W Laundry

ToriRating, 5 stars4 weeks ago
This Airbnb is perfect for a cozy staycation. It’s perfectly located to visit all the new places in Newburgh and close enough to explore Beacon so you get the best of both worlds! A true gem!
Guest favourite
Flat in Middletown
4.88 out of 5 average rating, 301 reviews

3 bedroom near Wesleyan, downtown

BangheeRating, 5 stars1 month ago
Very nice place and location is amazing. We were grateful that our host provide some basic amenities - coffee, shampoo and condtuoner, etc. Made our visit easy and very pleasant. Thank you!
Top guest favourite
Flat in Northampton
4.98 out of 5 average rating, 704 reviews

Tree Top Suite, cozy downtown apartment

DebbieRating, 5 stars2 weeks ago
Very clean and the detail and decor made our 1-week stay very comfortable, like being at home! Would definitely stay here again!

Family-friendly apartment rentals

Guest favourite
Apartment in Windham
4.88 out of 5 average rating, 191 reviews

Cozy Mountain hideaway Windham, Hunter

RandolphRating, 5 stars2 weeks ago
Pristine clean, cozy, one bedroom condo unit located in Windham with seasonal access to tennis courts and a pool. Walking distance to the beautiful Windham Path. Slept better than at home in the comfy bed. Went for two days of midweek remote work. Agnieszka, the host, was gracious and responsive. The host obviously put some genuine TLC into this place and it shows. Browsed for books at Briars & Brambles, an indie bookstore in Windham adjacent to Windham Pharmacy. Purchased groceries and firewood down the road at Hickory Hill Market . Ate in area at Higher Grounds and Windham Diner. Living room has a fireplace with large screen TV just above. Great for all seasons. Thanks Agnieszka!
Guest favourite
Apartment in Dover
4.91 out of 5 average rating, 110 reviews

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

MichaelRating, 5 stars1 month 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.
Top guest favourite
Apartment in Dover
4.99 out of 5 average rating, 120 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

MarkRating, 5 stars1 month 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.
Guest favourite
Apartment in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars1 week 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.
Superhost
Apartment in New Britain
4.82 out of 5 average rating, 121 reviews

New Britain "Joy of Small Space" Condo

JerryRating, 5 stars3 months ago
Muna is an awesome host. She is super responsive and always gives us good advise. We had a long stay and the place is very warm, clean, and very comfortable. Excellent location with everything you need, we had a wonderful stay and family vacation at her place. Thank you once again Muna, we look forward to come back again!
Guest favourite
Apartment in Stratton
4.94 out of 5 average rating, 170 reviews

Updated Ski in/Ski out Stratton Condo!

CelesteRating, 5 stars3 weeks ago
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!
Top guest favourite
Apartment in Lanesville
4.97 out of 5 average rating, 630 reviews

Stylish Condo Hunter Mountain

Tianna JoanneRating, 5 stars2 weeks ago
The place was exactly as described and she was really attentive if I had sent a message and it was extremely clean and cozy.
Guest favourite
Apartment in Stratton
4.94 out of 5 average rating, 103 reviews

Great 2 bedroom condo at Stratton Mountain

KatieRating, 5 stars1 month ago
Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!

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