Family-friendly vacation rentals in Stratton

We had a great stay at Bob's home in Ludlow. Big house accommodated our group of 7 comfortably. Great dining room and cute decor. TVs in all bedrooms. Very close to Okemo, restaurants and shopping. Hopefully will be back next year.

Nice place thanks Mike

Mark's High Pocket Bed and Barn was absolutely stunning and cozy. My friends and I stayed while attending a wedding nearby, and were so delighted by the home the minute we walked in. Thoughtful furniture and decoration through out the house, as well as beautiful yard and walking paths that were so nice to explore on a sunny spring day. The home was immaculately clean and well stocked. Mark was very communicative and responsive. We would all very happily stay at this home again!

My husband and I loved everything about our stay in the schoolhouse. It was just as adorable as the photos. The property is amazing and the views breathtaking, especially at sunset. The house is very private but you are close to amazing hikes, restaurants and shopping. Caroline had many recommendations but our favorite by far was The Chocolate Barn - the best ice cream ever! The sauna and hot tub was an added bonus. Not something I thought I would use to be honest but I enjoyed it every day of our stay. You won’t regret booking here - you’ll end up falling in love with this schoolhouse just like I did.

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.

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.

Our time at Eric’s chalet was amazing. The place was beautiful, peaceful, and extremely well maintained. It was perfect for a relaxing weekend getaway. We were in town for a wedding a few towns over, and coming back to this cozy spot after a night of celebrating was just what we needed. Eric was a super accommodating host. We had a family emergency that delayed our arrival, and he kindly gave us a few extra hours at checkout, which we truly appreciated. The home was exactly as pictured and very clean, with thoughtful touches throughout. The kitchen had everything we needed, and we loved unwinding in the hot tub. The laundry was also a big plus. We have already recommended Eric’s place to friends and would absolutely stay here again. Highly recommend!

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!!

Denis is a great host . What an amazing family and what an honor you let us stay! 100% will be coming back!

My family and I just returned home from a wonderful ski vacation! The home was just as pictured and the surroundings were absolutely beautiful!The house was immaculate and the ambiance was warm and welcoming. We had a great time skiing at Mt.Snow (30 minutes),exploring Brattleboro (12 minutes),preparing meals together and just spending quality time with each other! On another note….. Cat and Ed were very responsive and were always available if we had any questions! My family and I are already looking forward to returning next year ! Thank you again for EVERYTHING! Carol and Gene

We have family in Springfield so staying at Whitney and Alex’s place is perfect for us. It’s spacious and comfortable. This was our second stay and we will definitely be returning.

Place was clean, responded in a timely matter and looked exactly like the pictures! What a great experience ‼️

Terrific property! Magical landscape with a luxury treehouse at its center.

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.

If you need a small, private and peaceful location to kick your shoes off at the end of the day, this is your place. It was overall clean. The bathroom and kitchen were spotless. A light dusting would have really tied it all together. Linens were clean and there were extra blankets and pillows to choose from. Easy access down a quaint dirt road right off the main highway. We would return again.

Loved staying in this cozy cottage so much that this was our second time visiting. We love the town of Manchester and this place is the perfect balance of proximity to trails and shops/restaurants while still feeling like you’re staying in the woods.

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!

Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.

This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!

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.

What a perfect private getaway! Truly immaculate. Spacious. Comfortable. Peaceful.

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.

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

We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.