
Kid-friendly holiday rentals in Wilmington
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Top-rated family-friendly rentals in Wilmington
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Popular amenities for Wilmington family-friendly rentals
Kid-friendly house rentals

Cozy Modern Sugar House with spectacular views.
5 stars all around! The view and the setting are magical. The house is brilliantly appointed and designed. What a dream to stay in this house!! We want to come back for a stay in every season to experience it again and again! The interior is extremely cozy while being beautiful at the same time. One of the best Airbnb homes we've ever stayed in! Book your stay now -- you will love it!!

Vermont Botanical Studio Apartment
The place was quaint and peaceful. It was cleaned after we arrived which was not a problem. Oliver is very friendly. It could use new towels. Coffee and tea would be a nice touch.

Modern 3-bedroom A-frame in Londonderry w/ Pond
We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!

The Gate House--Experience Vermont!
We enjoyed our stay. Peter was a great host. Check in was easy and there were nice welcome touches when we got in. House was clean and in a great location. Will stay again in the future.

June in Vermont! (Pet Friendly)
This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.

FULLY renovated 1 bed/1 bath ski in-out condo!
My husband and I spent a long last winter weekend here. The condo was perfect for ski on/off and we enjoyed a day on the mountain. Though the weather wasn’t great the whole time, Brittany & Jen were quick to send recommendations for things to do, trails to hike and their favorite restaurants. So close to lots of great spots in this little mountain town. We would absolutely stay here again

Cheerful 1 bedroom cottage
Glenn was incredibly kind and responsive, and the cottage was exactly like the pictures. The space was perfect for a couple-day getaway before starting my MFA! Also, if you need good local recommendations, Glenn has you covered.

Steps to MoCA private house + SAUNA!
This beautiful vintage home is well cared for and spotless. A very pleasant and peaceful place to breath easy and rest after seeing the plentiful local sights.
Family-friendly apartment rentals

In town, newly renovated studio with private deck
stayed here the night before my wedding and carrie was such a great host! she was so accommodating and the space was beautiful. there were so many little touches that made our stay amazing! would stay here again!

Private two-bedroom suite within a two-story house
Lovely home in a peaceful secure neighborhood. Very easy to find and the instructions for entering the space were excellent. The apartment was exactly as pictured - very comfortable and spacious. We were there for 1 night - the beds were very comfortable & the space was spotless. Highly recommended if traveling through the area.

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

Contemporary forest eco-retreat, mountain views
We had a great visit! Millicent and Tony were very welcoming and responsive when we had questions, and the space was great—comfortable and a great view (when the weather cooperated). The recycling/composting rules are involved but they provided extensive explanations that made it easy to do the right thing. It was a chilly weekend but we stayed cozy, and the location was great for exploring Brattleboro and the surrounding area. We'll be back!

The Beer Diviner Brewery Apartment
Cindy was great with communications, and gave me all of the instructions I needed to make it a pleasant stay for me, my dog, and the hosts. I stayed Friday and Saturday nights, and enjoyed the craft beer and locally made sourdough pizza in the evenings with a talented musical duo playing on Saturday night. The taproom closes at 8pm, and after closing time the apartment is very quiet and peaceful. The apartment is cozy with attractive furnishings and a comfortable bed, but it is not a place for people with mobility challenges. There are 17 steps up to the apartment, and the shower in a free-standing claw-foot tub doesn't have handrails. I enjoyed my stay, and give it a 5-star review for physically fit singles or a couple!

Cozy Poultney Village Apartment
We had an exceptional stay at this Airbnb! It was perfect for two people with plenty of room. It was so cozy. We loved the Vermont specific decor. The ingredients for pancakes and the basic ingredients in the fridge were a thoughtful touch. I could not recommend staying here more!!!

Cooper's Place
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!

Rock River Retreat: VT Oasis Pet Friendly
It was a wonderful stay. Whether you’re just looking to relax or for a little adventure this stay offers it all. Even though it was a rainy stay they offer plenty of movies, books and games.
Family-friendly apartment rentals

Main St Escape | Explore Downtown Ludlow
Clean, great location, easy check in/out, and friendly host - would definitely stay again.

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.

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.

Okemo Clock Tower Base Ski-in/Ski-out Condo
We loved it. Although it’s not the newest or fanciest condo the location can’t be better right at the Clocktower Base. Our family of for had an amazing time snowboarding and exploring the area. Great restaurants close by and we will definitely be back next year.

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

Lovely 1-Bedroom condo with indoor fireplace!
Such an amazing place. Great location for walking to restaurant. Breath taking views especially the river. Extremely homey feel. We will definitely be back. thank you for your hospitality.

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

Mount Snow Close, Great Price, Lots of Room
Very close to Mount Snow. Walking distance to market, coffee house and Dover Bar and Grill. A dog friendly rental with everything you need for a ski trip.
Quick stats about holiday rentals that are kid-friendly in Wilmington
Total rentals
100 properties
Nightly prices starting at
₹7,721 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
Destinations to explore
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Albany Center Gallery
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Norman Rockwell Museum
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- The Shattuck Golf Club
- Dorset Field Club
- Canterbury Farm
- Otis Ridge
- Pineridge Cross Country Ski Area
- Hildene, The Lincoln Family Home
- Clarksburg State Park
- Ekwanok Country Club