
Family-friendly vacation rentals in Wilmington
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Wilmington
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Popular amenities for Wilmington family-friendly rentals
Family-friendly home rentals with a hot tub

Secluded Farmhouse Retreat - stunning views
This was a great home away from home. Wish it didn’t rain as much as it did. We really wanted to walk the grounds more. Inside was cozy and warm. Anything you needed it was there. Definitely thinking about coming back in the winter because it would be a perfect winter wonderland. Thanks again Sophon

Okemo Ski Chalet with Hot Tub
Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub
I had an amazing stay at this Airbnb! The space was beautifully decorated and incredibly comfortable, making it feel like a home away from home. The location was perfect, with easy access to local attractions and amenities. Caroline was a fantastic host, always quick to respond and very accommodating. I can't recommend this place enough and can't wait to return in the future!

Okemo-Ludlow, fireplace, hottub, sleeps 13
My friends and I had a great time at this place! The home was beautiful and very spacious - we were able to all hang out in the hot tub, kitchen, living room, and no place felt cramped.

Cozy Award Winning Farmhouse - hot tub and sauna!
Very beautiful home and lovely host! Would recommend!

Peaceful cabin close to skiing & Brattleboro
This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.

Expansive Lakehouse with Jacuzzi
My family and I had a wonderful time! Larry is very sweet, gave us a tour, offered to help with docking our boat and even offered my husband the tools to fix the bunk on our trailer. The house is big and beautiful!! Very clean, the beds are comfortable, the kitchen has everything you need!! The hot tub is definitely a bonus as we used it everyday!! The dock was perfect, we had room for our pontoon boat and jet skis. All around the perfect place for some R&R!!! My family and I love Cossayuna Lake as we are semi local and it was our first experience with an Airbnb. Thank you Larry for sharing your home!! Highly recommend this for your next vacation!!

Private Apt on Farm, Hot Tub with views!
We had an amazing stay! The beds were comfy. There is a local grocery store near by. We went snowboarding at Mt snow which was about a 25 min drive - not bad at all! The hot tub was perfect and the views were stunning. We loved Robert’s Glass blowing class as well.
Family- and pet-friendly home rentals

Cozy Log Cabin near Stratton/Mt. Snow-pet friendly
Christina was an excellent host who ALWAYS responded to any of my questions or concerns immediately and courteously. Her space was exactly as described and very spacious as well as a fantastic environment for a group to get together and have a great time! I highly recommend Christina’s place for a great time with a large group, she is the ideal host who works tirelessly to provide an amazing space for her guests!

Dog Friendly Studio
This was our sixth visit to Maple Hill Farms — we just can’t get enough of it! Philip truly the best host, and his home is pure magic. We’re so grateful to have met him and to experience his incredible hospitality and a property filled with the most amazing creatures.

Walk to Village/Lake Whitingham
We went to Vermont to hike and had a wonderful stay with Emily. The place is very cozy and clean. The ability to walk downtown to shops and trails and around a safe, quiet neighborhood was very much appreciated. Beautiful property. Recommended.

Lilac Ridge Farm House
We had a great stay at Lilac Ridge! The house was near and spacious, plenty of room for our family. We stayed in quite a bit and enjoyed the farm (including a visit with the calves!) and the house. The little farm stand had some nice things, including fresh eggs, maple syrup, honey, and soap, all local. Ross and Amanda were super responsive and took care of all our needs. Thanks so much!

The Carriage Barn
We recently enjoyed a lovely stay at The Carriage Barn in Guilford. Our host, Katherine, was very responsive to everything we might have needed during our visit: a very easy check in and out process, detailed instructions on how everything worked, items for our comfort (a gift of delicious chocolates, many fluffy towels, silky sheets, etc.), and was easily available via texting. The photos of her restored historic barn are very accurate - it's a beautifully designed renovation and is decorated with lovely art pieces, cozy furniture, and a huge library of books for your enjoyment. The tv works great and so does the WiFii. We traveled with our small dog and there is a baby gate available that easily snaps onto the staircase posts so I was not concerned about my dog's safety.. Best of all is the beautiful views of the gorgeous Vermont countryside. You'll see lovely sunsets here and spectacular sunrises. It's a great spot to truly relax.

Apple Blossom Cottage: A Tiny House
I found this listing years ago while scrolling for tiny houses and it stayed in the back of my mind. I finally had the opportunity to visit as a getaway for my birthday. It was SO peaceful and lovely. I really enjoyed walking the grounds with my dog in lieu of taking a hike nearby, since there was so much rain during my stay. Dominic even let me take a walk to his other property, which was so spacious and pretty as well! I spent most of my time journalling and getting clarity while sitting in the swing on the porch, listening to the rain. I also took a brief voyage to Manchester Center, which was a darling town with lots to explore. I recommend Depot 62 for super tasty Turkish food. The cottage had all the essentials and clear instructions. It could use a deep clean in some of the nooks and crannies, but was overall very tidy and well-kept. I would 100% come back. The vibe up there in the misty mountains of VT is just so high and so freeing. Such a re-aligning stay.

Stone n' Sky Lodge
I genuinely don't know what to say other than the fact that this may be one of the greatest places I've had the honor to lodge at. I did a lot of vetting across New England to find a wonderful place that could sleep a decent amount of people, provide a scenic and comfortable escape, and keep us entertained. Sarah's wonderful Stone and Sky Lodge exceeded every expectation I just listed. It's cozy, warm, and feels like a hidden nook! The scenery and nature couldn't be more beautiful. I never got the pleasure to meet Sarah, though I wish I did. Over messages and from what my friends told me, I just know that Sarah is the most hospitable and kind host that I've talked with in a while, and I hope that next time I can thank her personally. From my friends and I, we thank you for sharing your home with us. If you think that the excellent reviews are too good to be true, don't. This IS the truth, and I can't wait to have another reason to come back to this wonderful treasure of a place.

Rock River Retreat: VT Oasis Pet Friendly
Truly a magical place… the views are amazing. We actually frolicked in the river a bit even though it’s only April and there was small amount of snow on the ground… it was surprisingly refreshing for a feet dip… as far as the unit there was so much charm and care put into this place… we had a snack and beverage awaiting us and Carmella the cat had a snack and toy with a little pillow bed by the window and food dishes ready to use. These extra little touches are special ❤️ The inside is super cute and charming, I loved the bath tub…. I stayed 2 nights and took 3 baths 😂 after our 5 hr drive my daughter needed to use facilities but it took her a good 10 minutes because she loved every detail of the space. I hope to return in summer! Book this space if interested, I promise you will not be disappointed!
Family-friendly home rentals with a pool

Bear's Den - Mt Snow Townhome w/ Heated Pool!
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.

Rustic Sunny Vermont Home near Mount Snow
Couldn't say enough great things about both the hosts and the property. Just lovely home - very spacious, and clean and cosy. The area is gorgeous, with a lot to do. Mt. Snow and Hermitage skiing are very close, and Wilmington and the area are charming. Host was very gracious and kind..thank you!

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.

6 BR Perfect Private Retreat in Vermont!
Large house in a very remote area. Approximately 70 acres. It was very relaxing and was nice to enjoy the pool which was professionally cleaned before arrival. The master bath has an incredible view of the mountains and an enormous shower. Pool table was fun and well taken care of. We stayed on probably one of the hotter weekends and the house cooled down at night pretty well just by opening the windows. Most rooms had ceiling fans if no other fans were provided. I can imagine this house would be amazing in the winter or fall too. With the screened in fireplace room and additional fire place inside the main house. You’re also close to 2 ski mountains each about 18 miles away. I could see myself renting again in the future. Thanks again

The Villa - Industrial Farmhouse with Hot Tub
We absolutely loved staying here- beautiful and laid out perfectly for 2 families, each with 2 little kids. Super convenient location to Mt. Snow. We look forward to staying here again!

Bright, Large, Spacious Family Home
We had a very relaxing stay. Plenty of space to stretch out. Located within 10-15 min. of Keene State activities, the purpose of our trip. Bryan was a wonderful host. Very responsive. Instructions were clear, directions very helpful. Everything we needed!!

One Bedroom Suite Near Okemo
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.

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.
Quick stats about vacation rentals that are family-friendly in Wilmington
Total rentals
260 properties
Nightly prices starting at
$125 CAD before taxes and fees
Total number of reviews
9.9K reviews
Pet-friendly rentals
110 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
120 properties have a dedicated workspace
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- Stratton Mountain
- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Saratoga Race Course
- Saratoga Spa State Park
- Albany Center Gallery
- Berkshire East Mountain Resort
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Pineridge Cross Country Ski Area
- Naumkeag
- Otis Ridge
- Ekwanok Country Club
- The Shattuck Golf Club
- Hooper Golf Course
- Bousquet Mountain Ski Area
- National Museum of Racing and Hall of Fame
- Northern Cross Vineyard
- Huck Finn’s Playland, Albany