
Family-friendly holiday rentals in Middlebury
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Top-rated family-friendly rentals in Middlebury
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Popular amenities for Middlebury family-friendly rentals
Family-friendly home rentals with a hot tub

Macintosh Hill Farm
A wonderful ski weekend! We spent two nights and spent the day (Saturday) skiing at Killington. Quiet drive there and back so it was a perfect location to come back to a peaceful evening. Hot tub was amazing after skiing and very clean! Laura and Aaron were very helpful and let us know the conditions of the roads prior to our arrival. Flexible, kind and friendly! Would stay again for sure.

Honeymoon Cabin with Jacuzzi Tub
We came up for a few nights to elope in the mountains with our two dogs. Meghan was so accommodating. This is our second time at this cabin but plan on making this our go to vacation spot when we come to Lake Placid!

Charming getaway tucked away in the Green Mtns
I booked a last minute escape from the city and Rob’s mountain getaway was exactly what I needed. The home was both welcoming & comforting with enough blankets to keep me & our furry one warm and cozy. The stocked coffee bar & equipped kitchen made the mornings a breeze. Tucked away in the peaceful mountains of Vermont, stargazing takes on a whole new meaning while in the amazing hot-tub Rob has on the property. The weather was too variable for us to utilize the lovely fire pit but that’s what the winter time is for. Still peaceful to sit up in the ski chairs and enjoy the scenery. We even saw a hummingbird! All in all, Rob is an amazing host with a home filled with so much character and charm. The local restaurant recommendations were all a hit! It’s a quick 30-40 minute drive to Burlington We even extended an extra day because we enjoyed our time so much and Rob was quick to reply and enthusiastic in all communications. 10/10 will stay again and highly recommend!

Lower Yurt Stay on VT Homestead
Beautiful spot to relax, reconnect and leave refreshed! We enjoyed everything about our stay, especially the sauna, living pool, and hike to the yurt! We would love to return, thank you for sharing such a peaceful place with us, it was exactly what we needed.

Hilltop Haven
We had a wonderful stay at the Monty's place -- the apartment was well stocked with many thoughtful items, the area is very peaceful and near to outdoor activities, and the hosts were friendly and responsive. Would definitely stay again! Thank you!

Breathtaking View, Hot Tub, Sauna, Pets Ok!
We completed the lake placid 9er hike on our stay. Great location with all hikes less than 20 min away (some less than 10). Spectacular view and incredible kitchen. Hot tub and sauna were great amenities for recovery from long days hiking. Place is as advertised and you cannot beat the view of the mountains. Highly suggest going to the hungry trout restaurant. Only a few minutes away, much closer than downtown lake placid and the food/service was great. Highly recommend this rental and hope to be back next year to begin the 46er.

#7 - Hemlock Hideaway Cabin
Home now after a couple days at the cabin. Feeling fully rested and can’t express enough how much we needed this getaway. Ago and Marty go above and beyond to make you feel comfortable and provide you with everything you could need to relax and have a great time. We will be coming back here. Hopefully soon.

The Barn at Fielder Farm
What a beautiful place! Sarah and Bert’s place was one of a kind! Superb location with beautiful views of the surrounding mountains! We booked this location for our family snowboarding trip, there was ample space for us to eat and enjoy family time. Great kitchen to cook and socialize with everybody. I can’t say enough about this home. Sarah and Bert were excellent hosts and we communicated effortlessly and they provided a very positive experience. If you’re planning a trip to the area for adventure or just a getaway, I would highly recommend staying at Fielders farm!
Family- and pet-friendly home rentals

Schroon River Cabin
Bob and Joan’s cabin was absolutely spectacular. Overall this place is the perfect mountain getaway! This place has all the amenities you could need, prime commute to surrounding ADK regions, and let’s not forget the breathtaking views. This place exceeded our expectations and was exactly what we needed for a get away to the mountains with the dog. Bob was an amazing host and we look forward to coming back, as well as passing along this gem to friends and family to also book with Bob & Joan!

Tiny House at Camp Comyns
We loved how she had breakfast items stocked for us! The beds were so comfy and the tiny house was so cute! Enjoyed our stay!

Hideaway Cabin by the Stream on 27 Acres
Our stay was incredible! The view by the stream was amazing, everything was so peaceful and perfect. Inside the cabin was exactly what we expected, very homey, everything we needed. We loved the walls lined with books! Kevin was very attentive towards what we needed - it stormed all day Saturday and he brought a second heater for us because the temperature dropped, which with that and the gas fireplace, kept the place perfectly warm and comfortable. He was also very accommodating in allowing us to stay an extra night since our plans of hiking all weekend were thwarted by the rain. We went for my husband's 40th birthday and i couldn't have picked a better place to get away from the stress of life. We plan on going back for sure!

House in beautiful rural Plainfield
My daughter and I had a wonderful stay. Gail and her husband were the nicest hosts. We had some great chats. The area is absolutely beautiful and peaceful.

Wilmington Range Log Cabin on the AuSable River
Beautiful cabin in the woods that isn’t too far from anything but feels isolated just the same. Terrific base of operations to access many trailheads, Lake Placid and Saranac Lake. Restful and low maintenance stay. We would recommend and visit again.

Secluded Waterfront Chalet Near Whiteface
We had a great time at Still Point & the surrounding areas. The house was well stocked with supplies. It was clean (keep in mind you are in the woods & mountains) & well maintained. Michael & Isabelle were easy to communicate with & quick to respond. The scenery around the house was beautiful & relaxing. Listening to the Loons just about every day & watching the beavers frolic one night was amazing. The surrounding areas & attractions were easily accessible & just a short drive. Yet, you felt like you were all alone & secluded when at Still point. Our kids had so much fun at the house & on all the adventures we took. The only downside was leaving! Thank you, Michael & Isabelle, for sharing your home & providing lasting memories for our family!!!

Stetson Hollow Cabin by Stetson Brook
Adorable, cozy cabin 10 minutes from Sugarbush ski resort. Very relaxing atmosphere. Well stocked with linens and firewood. Jill left us a little delicious treat. Would stay here again

19th Cty Vt Farmhouse 100+ Acres
Beautiful property and views. Great for family attending wedding nearby. Bonus was we were able to rent the house across the street for additional family & friends. Would rent again.
Family-friendly home rentals with a pool

Chilson Brook Alpacas
Beautiful stay with incredibly kind hosts! Pool was lovely and the alpacas were so much fun to pet. Would love to return

Ski In/Ski Out with upgrades!
My husband and I stayed here to do a few days of spring skiing at Sugarbush. The location is perfect, a short walk to the slopes when there's snow. Two-minute drive to resort if snow is sparse. Sugarbush is a huge resort and has many options for all skills of skiing. The condo was spotless and had a full kitchen with plenty of pots and pans, etc. It was very comfortable and also had a selection of books and games to choose from. Host was very responsive and gave perfect instructions. Thank you!

Relax in Recreation Paradise!
Chad was an incredible host! He was extremely accommodating with any requests we had. The views from his place are breath-taking! We enjoyed snowshoeing from the backyard onto trails in the woods. I fell in love with his cat who visited daily! He kept the driveway plowed and salted in a timely fashion. We enjoyed our stay and would highly recommend his place!

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO
Extremely nice cabin, very recently renovated. The owner has a keen eye for organization, everything is neatly placed where it should be. Linens are clean, beds were super comfortable. Amazing stay, thank you Cathy

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.

Gorgeous panoramic views - 4 miles to the mountain
We had a great stay! The place is 4 different levels with plenty of room for the 5 of us. The kids loved the loft bedroom and they all had their own comfortable bed to sleep in. The views are amazing and it was so quiet! I could have lived in the hammock on the deck!

Cute Cottage - Poolside - Minutes To Activities
Linda was a fantastic host, and her home was even better than listed. The cabin was a good size for our family of four + dog; the 2 bed / 2 bath arrangement allowed for good privacy when needed. The fireplace was great for apres and winding down at night. Location is a nice mix of seclusion (off the Mountain Rd), but close to everything.

Hike bike golf 1 bedroom 1 nght Ok Aug is open
We enjoyed the stay. Good weather so did not need AC. Good thick towels.
Quick stats about holiday rentals that are family-friendly in Middlebury
Total rentals
40 properties
Nightly prices starting at
$149 NZD before taxes and fees
Total number of reviews
2.2K reviews
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
40 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
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- Sugarbush Resort
- Okemo Mountain Resort
- Smugglers' Notch Resort
- Gore Mountain
- Bolton Valley Resort
- Spruce Peak
- Pico Mountain Ski Resort
- Cochran's Ski Area
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Fox Run Golf Club
- Country Club of Vermont
- Northeast Slopes Ski Tow
- Ethan Allen Homestead Museum
- Vermont National Country Club
- Leahy Center for Lake Champlain
- Lucky Bugger Vineyard & Winery
- Montshire Museum of Science
- Burlington Country Club
- Killington Adventure Center
- Adirondack Extreme Adventure Course
- Lincoln Peak Vineyard