
Family-friendly holiday rentals in Stratton
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Top-rated family-friendly rentals in Stratton
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Family-friendly home rentals with a hot tub

Top of the World! Jacuzzi! Private Hiking Trails!
Nice place thanks Mike

Secluded Farmhouse Retreat - stunning views
We were four retired couples. Worldly travelers used to very comfortable surroundings. No TV was fine for this occasion. The farmhouse is designed with furniture comfortable for all, appointed in a farmhouse motif, of course, but the design aesthetic is of a quality respectful of its guests. "Good enough", never is. Obviously, the quality of consideration our Host has for the farmhouse presentation is treat your guest with respect and it will be reciprocated. One of the individuals commented, prior to even unpacking: "Perfect Place!" While it rained, we did not have the opportunity to enjoy the firepit, but some enjoyed the Hot Tub, as we all talked late into the night. This is located "close enough", 10 min drive to "civilization", to sites and shopping but it's really a more slightly secluded, private environment whereby a large family or, like us, distinct families can share comfortably, "come and go" separately together or stay together, together. We enjoyed ourselves.

Okemo Ski Chalet with Hot Tub
Stop scrolling, you found your next vacation. Bob is a fantastic host with a stunning home. We have stayed with Bob many times and he continues to invest in the property and ensures your stay is nothing short of fantastic. Cannot recommend the ski chalet enough.

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.

Stunning Rustic Apple Barn - hot tub & sauna
We had a wonderful stay! It's such a beautiful and unusual cabin. It would be great for two couples as there are 2 equally great bedrooms that are quite separate, and a very nice sitting area around the amazing wood stove. (Which we didn't use because it's June and not necessary.) The hot tub was such a treat, and the bedroom with the boat was so cool. (OK, so maybe the bedrooms aren't quite equally great.) The kitchen is outstanding! We sat out on the porch a lot looking over the meadow, and I really liked that we were able to bring our dog. About the notes and instructions: they didn't bother us at all. There's a few non-intuitive features of the cabin, and it was useful to have clear guidance on those things. I want to make clear why I gave 4 stars for "cleanliness". I think they do an excellent job cleaning this cabin! But a rustic cabin like this is impossible to make "5-star clean". If you want or need that level of cleanliness, then "rustic" isn't for you! Go find a nice hotel.

Ski Chalet with Hot Tub on Okemo Mountain
Had an awesome weekend here with the family! The cabin had everything we needed, super comfy and well-stocked. The hot tub was a huge bonus, and the hosts were super friendly. Would definitely come back!

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!!

Spacious Renovated Barn Apt on 100 acres!
My wife and I have visited twice already and hope to go back again soon. We met the owner and her wonderful fiancé while we were visiting. Wonderful people. Very private and beautiful location. If you need to unwind and relax this is the location for you. Thank you for hosting us and congratulations..
Family- and pet-friendly home rentals

Walk to Village/Lake Whitingham
Great little studio apartment attached to Emily’s house, very peaceful yet walkable to downtown Wilmington!!! Easy to get to the Hoot and Toot trail, and about a mile from the boat launch/picnic grove at the lake!! Absolutely would recommend and stay again!!

Pinecone Pond
We had the most lovely stay at Pincone Pond. The house is absolutely spotless and well stocked with everything you need in the kitchen, shampoo and condition in the bathrooms and throw blankets for the cool evenings. The house is so homey and comfortable and the grounds are stunning. Beautiful yard and pond which were well cared for. Catherine has thought of everything including chairs for sitting by the pond or fire pit. Just a lovely, peaceful spot.

400+ Airbnb Visits: Incredible Mountain Cabin
We had a wonderful stay at Ali and Carson’s cabin! They were incredibly helpful and welcoming hosts. The Mountain View from the cabin is absolutely stunning, even with the rainy weather, it was breathtaking. We also enjoyed exploring the charming nearby towns, and our two dogs had a great time as well. Despite the rain, we loved our stay and are already looking forward to coming back when the weather is better. Highly recommend!

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER
Wonderful place with great family room with fireplace especially when your weather doesn’t cooperate. The house is well kept and the instructions for everything were placed all around where needed. Fenced yard was great for the dog. The bed in the master is super comfortable with great linens. Loved the house-would live in it in a heart beat. Plenty of games, air hockey table, darts and another game table…grill, firewood- even poop scoops for the dog! Well done!

19th c. Barn in The Berkshires
Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.

Hickory Ridge, Vermont Log Cabin, no cleaning fee
Fantastic and authentic Vermont experience. Top 3 AirB&Bs I’ve stayed in. Off the beaten path, but close enough to everything you need. Rik is great host and makes it easy. Book if you can find availability.

Sunrise Cabin
Susan and Carmen's place was just as advertised. We really appreciated their flexibility on check-in and it was nice meeting Carmen to show us around. The space is very cozy and comfortable. The cabin is well equiped with all the items you need for a stay, as well as some toys that my young daughter enjoyed playing with. There was a sulfur smell with the hot water, but I know Carmen is working to resolve that and we were told the water is safe to drink. Beautiful views and close to Magic MTN and Ludlow. I'd love to stay there again.

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres
Rita’s chalet is really clean and the view around it is amazon. The place is well stocked with games for fun and firewoods for warmth. Upon request, Rita was able to accommodate our late checkout request with a reasonable surcharge. We have enjoyed our stay at Rita’s place and would definitely come back next time when we are around
Family-friendly home rentals with a pool

Magical Farm Getaway - a must visit!
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!

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.

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.

Moon Valley Country Retreat no clean fee pets yes
This is a wonderful place to stay. It’s very clean and the hosts have prepared for everything. It feels like your own cabin in the woods. Plus there are so many activities in a short distance of the place.

Cozy Bear- 1 mile to Mt Snow Ski Home
We really loved staying here. The location was perfect and the accommodations were fantastic. Our host was exceptional in making sure we were comfortable and informed. We will definitely try to book again.

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.

1st Fl Condo 3BR @ Stratton Sleeps 7 Pool Hot Tub
Our stay at Carl’s listing was more than we could ask. The location is perfect to the mountain and the shops and restaurants in the village. Carl was very helpful for the check in process and was very responsive. The space was very large and clean. We had the best time and I would certainly stay here again in the future!! The amenities at the lodge were amazing and the lodge manager was so incredibly helpful and friendly as well. A happy and fun vacation!!

Hollywood Bungalow in the Berkshires #C0191633410
Diana and family were amazing super friendly, accommodating and checked in on use through out. We arrived later than expected but Diana waited for us and showed us around the property. We even got to see her dogs, meet her family, met the horse on the property behind and great conversations with Diana. She made us feel right at home. She prepped the pool for us, left us some good snacks and offered lots of recommendations. When you visit check out the theater set up, it’s pretty cool with insane sound system and clear video. Comfortable beds and all around beautiful property. If you visit in the summer it is a little warm on the second floor but we cooled off in the pool and just made sure to turn the fans on. It was the perfect birthday trip, relaxing, private and homey. My family and I are already looking forward to the next trip. Thank you to Diana for everything and hope we can meet again! 100% recommend.
Quick stats about holiday rentals that are family-friendly in Stratton
Total rentals
150 properties
Nightly prices starting at
₹7,740 before taxes and fees
Total number of reviews
3.9K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- West Mountain Ski Resort
- Saratoga Spa State Park
- Pico Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Stratton Mountain Resort
- The Shattuck Golf Club
- Lake George Expedition Park
- Magic Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Bretwood Golf Course
- Bromley Mountain Ski Resort