
Kid-friendly vacation rentals in Wilmington
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Top-rated kid-friendly rentals in Wilmington
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Kid-friendly house rentals

Magical Farm Getaway - a must visit!
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

Clean, Captivating VT Farmhouse near Stratton!
Great house, amazing location near Stratton, and Matthew was just great. He was super communicative, and went above and beyond to make sure we were happy with our stay. We'd love to return again.

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.

Quiet Vermont Home with Amazing View
House was clean, spacious, and conveniently located for our trip to Williamstown. And the hosts were extremely responsive - we had no issues during our stay. Thank you!

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.

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!!

4 Bedroom Family Ski House w/ WiFi, cable!
House was as described, very private and was equal distance between Okemo and Magic Mountain which was what we were looking for which worked out perfect for our ski vacation. Very close to Weston too! As Brian mentioned, definitely suggest 4WD vehicle to access house during snowy winters.

Modern farmhouse close to Montague Retreat Center
We had an incredible stay at this beautiful home in Montague, MA. After two failed bookings due to hosts not updating their availability, we were so relieved to find this gem—especially since we were traveling for a funeral, which was already a stressful experience. The host was incredibly accommodating and allowed us to check in early, which was a huge help. From the moment we arrived, everything was perfect. The check-in process was seamless, and the home itself was immaculate, cozy, and beautifully designed. The steam shower and tub were absolute highlights—such a luxurious touch! I cannot recommend this Airbnb enough. If I find myself back in the area, I would book again in a heartbeat. Thank you to the host for making our stay so comfortable and stress-free!!
Kid-friendly apartment rentals

Charming Art Filled Apartment
Excellent location and decor, responsive host, off street parking, beautiful beds. Lots of art, all genres and media, an eclectic style with loads of personality. Our second time staying and we will be back again.

**Happy Hour! Gorgeous & Modern Downtown Retreat**
Beautiful apartment in the center of Wilmington. We own land and have our camper set up in the next town over, but with the cold weather lately, the camper is still winterized. We wanted to come up and get some yard work done and stay locally, and this apartment was the clear winner! Walking distance to our favorite coffee shop, lots of restaurants, my favorite bookstore (!!) and walking trails. Loved the deck- even though it was April and iffy weather, we were able to have takeout dinner outside one night! So grateful that Jennifer allows pets, as we have two dogs and it’s often hard to find pet friendly Airbnb accommodations that are in a good location and as clean as this place! Jennifer was so kind, accommodating and responsive. She went out of her way to make sure we had a great trip- she’s definitely one of the best hosts we’ve had! Thank you for making this week wonderful! We will be back.

Quiet St in Town, gardens, terrace
We loved Jaki's apartment. It was very clean, neat, beautifully appointed, and convenient. Jaki welcomed us when we arrived and made herself available. She was friendly, warm, and very responsive. I'm returning to the area for business in the future and will book the same apartment again.

Big, sunny 1893 flat steps from Bridge of Flowers
This was our third stay at Susan's place. This stay was great like the others. The apartment is cute and cozy. It's in a perfect location. We love having restaurants, shops and coffee right outside our door.

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.

"Up Top” at Ro & Oak House
Had a great time at Hannah’s place. Excellent location, beautiful space, comfortable beds. No complaints!

Apartment on Main Street
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.

The Carriage House Loft: Seasonal Stays
This property is a very welcome getaway and we felt right at home. Thanks again! I'll be back again. 👍
Kid-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.

Ski In/Out, Cozy 3BR Condo steps to Village
Exactly as described. Beautiful condo, right in the heart of Stratton. Easy ski in/ski out. Excellent proximity to everything the village has to offer. The kitchen is well equipped and the bedrooms are really comfortable. Brian was a great host! We will absolutely book again for future Stratton ski trips!

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!

Great 2 bedroom condo at Stratton Mountain
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!!

Cozy condo within walking distance to the slopes.
You really can’t beat this location. It’s across the steet from the lifts and the village with lots of restaurants/bars/stores. The space was perfect for our family of four. Our two young children stayed on the pullout and we thought the king bed was quite comfy. We would def stay here again!
Quick stats about vacation rentals that are kid-friendly in Wilmington
Total rentals
100 properties
Nightly prices starting at
ﺩ.ﺇ331 before taxes and fees
Total number of reviews
5.5K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
20 properties have a pool
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- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Albany Center Gallery
- Monadnock State Park
- Berkshire East Mountain Resort
- Saratoga Race Course
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Otis Ridge
- Norman Rockwell Museum
- Naumkeag
- Hooper Golf Course
- National Museum of Racing and Hall of Fame
- Peebles Island State Park
- Northern Cross Vineyard
- Pineridge Cross Country Ski Area
- Huck Finn’s Playland, Albany
- Willard Mountain
- Hancock Shaker Village