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Kid-friendly vacation rentals in Pioneer Valley

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Pioneer Valley kid-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Brattleboro
4.94 out of 5 average rating, 122 reviews

Spacious Brattleboro home on river, walk to town

DebbieRating, 5 stars2 months ago
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.
Top guest favourite
Home in Stockbridge
4.97 out of 5 average rating, 110 reviews

Greek Revival Farmhouse

CourtneyRating, 5 stars2 months ago
Michelle was incredibly gracious and responsive when we called late after our check in with a question about the heater. The place is gorgeous and you can tell that she pays attention to every detail and is doing all she can to make it a pleasant stay. The decor is perfect, the amenities are perfect. We had plenty of room to cook and host a dinner with four adults and two kids. We lit a fire, played games and relaxed. The bedding is so comfortable and we all slept so well.
Superhost
Home in Otis
4.94 out of 5 average rating, 144 reviews

Berkshires hideaway! Hikes & serenity near lake

MaryRating, 5 stars4 months ago
Niki and Adam’s place was wonderful! Space for everyone, well equipped, comfortable and clean. Communication responses were quick and clear. All 3 generations of my family thoroughly enjoyed their home and its surroundings. Highly recommend!
Top guest favourite
Home in Pittsfield
4.95 out of 5 average rating, 169 reviews

Cantabile life in the Berkshires

GreggRating, 5 stars1 week ago
Had a great stay. Beautiful property and close to everything.
Guest favourite
Home in Wilmington
4.88 out of 5 average rating, 106 reviews

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

JamesRating, 5 stars2 weeks ago
Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.
Guest favourite
Home in Easthampton
4.89 out of 5 average rating, 57 reviews

Charming 4 bd/2 bth home near Williston

NarcisRating, 5 stars3 months ago
Katrina was an amazing host! She was incredibly responsive and hospitable throughout our stay. When we requested an iron and steamer, she promptly provided them, which was so thoughtful. On top of that, she proactively put ice on the property’s steps during a snowy Saturday to prevent any accidents—such a considerate touch! The property was clean, comfortable, and well-maintained. Katrina’s attention to detail and care for her guests really stood out. Highly recommend staying here!
Top guest favourite
Home in Dover
4.88 out of 5 average rating, 251 reviews

Mt Snow retreat, ski & summer

TimothyRating, 5 stars1 month ago
Wonderful stay in Vermont! Very spacious home with an amazing dining room and theater room in the basement ! Location was perfect for a visit to mt snow, just a few minutes away, and theater room home was cozy, 2 fireplaces , and wonderful! Recommend!!
Guest favourite
Home in Lee
4.97 out of 5 average rating, 100 reviews

Stylish Mid-century Modern Berkshires Cape

LarryRating, 5 stars1 month ago
The home was very clean and as described with everything we needed for our visit. Chris was very clear with his check-in instructions and quickly responsive to questions as we got settled. I would stay here again.

Family-friendly apartment rentals

Superhost
Apartment in Lenox Dale
4.91 out of 5 average rating, 129 reviews

Charming 2BD apartment.

BrandonRating, 5 stars5 months ago
Beautiful, clean home just a few minutes away from the centers of Lenox or Lee in either direction! We had a great time relaxing and enjoying the food nearby :)
Guest favourite
Apartment in Shelburne Falls
4.87 out of 5 average rating, 431 reviews

Big, sunny 1893 flat steps from Bridge of Flowers

CathyRating, 5 stars1 week ago
Location can’t be beat! This is our second stay in one of Susan’s apartments and the basic needs — linens, dishes, tea etc—are well provided for. She has artful taste which we really appreciated. They also contacted us when we left a shirt behind. They are upfront about the smoke in the stairwell , but the smell does seep into the back bedroom a bit. Also, we were there in April but the building heat was still running. It took us a while to realize that is why it was so stifling hot. We ended up using the AC units to make it comfortable enough to sleep.
Superhost
Apartment in West Brattleboro
4.76 out of 5 average rating, 131 reviews

Cute, Convenient with Big Backyard

MichaelRating, 5 stars4 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.
Guest favourite
Apartment in Burlington
4.85 out of 5 average rating, 108 reviews

Charming apartment with breathtaking view!

RebeccaRating, 5 stars8 months ago
Stayed here for 2 nights with a couple friends. Perfect spot for a quick getaway. Backyard and pool area was exactly what we were looking for with lots of space to lounge and relax. Lots of entertainment if you wanted to just hang inside as well. As some of the other reviewers noted, you can definitely hear the hosts move around upstairs. Didn't impact us too much except for Saturday morning. Was a little difficult to sleep in b/c of the noise.
Top guest favourite
Apartment in Northampton
4.92 out of 5 average rating, 620 reviews

Sunny Peaceful Home

AndreaRating, 5 stars1 week ago
My daughter and I were seeking a basecamp to explore nearby colleges but also had one day where we needed to connect to our computers for work. We slept well, had peaceful morning walks in the neighborhood, took advantage of the sunshine on the lovely deck, and enjoyed making meals in the kitchen that had more than all the essentials.
Guest favourite
Apartment in Northampton
4.85 out of 5 average rating, 549 reviews

Parkside downtown cozy apartment

MicheleRating, 5 stars1 week 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
Apartment in Northampton
4.85 out of 5 average rating, 748 reviews

Down town Florence Temperance Hall

NancyRating, 5 stars3 weeks ago
This was our second stay and would certainly return again. Love the openness of the living area, the great bathroom and the kitchen amenities. Quiet location, was perfect for our activities in Northampton.
Guest favourite
Apartment in New Lebanon
4.95 out of 5 average rating, 131 reviews

Sunny Duplex at the old boarding house

ScottRating, 5 stars10 months ago
The place was wonderful. Very charming and homey, spotless with all the amenities and conveniences you could need. The information included in Joe’s binder gave great recommendations for meals and attractions within easy driving distance. We had never traveled to that area before and found the local scenery beautiful. Thanks for a lovely experience!

Family-friendly condo rentals

Guest favourite
Condo in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars2 months ago
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.
Guest favourite
Condo 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
Condo 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
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars2 weeks 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.
Guest favourite
Condo in Dover
4.84 out of 5 average rating, 119 reviews

Walk to Mt. Snow-Spa-Summer Pool

GaryRating, 5 stars1 month ago
Great little studio spot to use as your Basecamp for activities in the area!
Superhost
Condo in Dover
4.77 out of 5 average rating, 142 reviews

3 Bedroom, 2 Bathroom Condo, 2 Mins to Mount Snow!

DanielRating, 5 stars1 month ago
Great location and perfect house to stay in
Guest favourite
Condo in Dover
4.89 out of 5 average rating, 9 reviews

New - walk to Mt Snow w/ Tub & Gym

ToniRating, 5 stars2 months ago
We loved the proximity to Mount snow, and the layout of the place was cozy and comfortable. We loved the newly renovated kitchen and all kitchen supplies were new. We didn’t get to use the amenities but we loved the sauna and hot tub offerings!
Guest favourite
Condo in Hancock
4.86 out of 5 average rating, 152 reviews

Cozy Condo @ Jiminy Peak

ElizabethRating, 5 stars2 months ago
We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.

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