
Kid-friendly vacation rentals in Pioneer Valley
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Top-rated kid-friendly rentals in Pioneer Valley
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Popular amenities for Pioneer Valley kid-friendly rentals
Kid-friendly house rentals

Spacious Brattleboro home on river, walk to town
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.

Greek Revival Farmhouse
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.

Berkshires hideaway! Hikes & serenity near lake
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!

Cantabile life in the Berkshires
Had a great stay. Beautiful property and close to everything.

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

Charming 4 bd/2 bth home near Williston
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!

Mt Snow retreat, ski & summer
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!!

Stylish Mid-century Modern Berkshires Cape
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

Charming 2BD apartment.
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 :)

Big, sunny 1893 flat steps from Bridge of Flowers
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.

Cute, Convenient with Big Backyard
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.

Charming apartment with breathtaking view!
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.

Sunny Peaceful Home
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.

Parkside downtown cozy apartment
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.

Down town Florence Temperance Hall
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.

Sunny Duplex at the old boarding house
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

Mount Snow Ski Chalet
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.

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.

Winter 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.

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.

Walk to Mt. Snow-Spa-Summer Pool
Great little studio spot to use as your Basecamp for activities in the area!

3 Bedroom, 2 Bathroom Condo, 2 Mins to Mount Snow!
Great location and perfect house to stay in

New - walk to Mt Snow w/ Tub & Gym
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!

Cozy Condo @ Jiminy Peak
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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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Monadnock State Park
- Six Flags New England
- TPC River Highlands
- Berkshire East Mountain Resort
- Taconic State Park
- Mount Snow Ski Resort
- Bushnell Park
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Hartford Golf Club
- Douglas State Forest
- Naumkeag
- Beartown State Forest
- Otis Ridge
- Brownstone Adventure Sports Park
- Rockledge Golf Club
- WIckham Park
- Keney Park Golf Course
- Talcott Mountain State Park