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

Magog studio - Waterfront - Cozy and confortable
Great stay! The place was clean, comfortable and in a great location for our activity in the area. I recommend this place without hesitating!

Cozyluxe! Chic and warm condo with hot tubs!
A very good spot close to the mountain. A cute bar across the road, and the hot tubs were a great way to close the day.

3 BDR Mtn Home near wedding barns, Smuggs/Stowe
Samantha and Chris's place was a perfect spot for a Smugglers Notch getaway! it's a beautiful home, perfect for a family of 4. Even in cold temperatures( at -5F and lower) with lots of snow, the place was cozy warm with the wood burning furnace (clean and devoid of smoke) as well a propane heater downstairs. Literally 2 turns from the slopes of a great family ski mountain! But the views and location of the property were amazing for those wanting to do other things than ski. Samantha was responsive and an excellent communicator. I have to throw in that everything in their kitchen was in excellent condition (every appliance) including sharp functional chef knives (an uncommon phenomenon for a renter) Thank you Samantha and Chris! Sharing your home with us was a touch- stone of great new family memories!

Apartment, comfy and cozy with kitchen/gas fire
We really enjoyed this place! The property is beautiful. The pool looked really clean and well cared for (but we didn't have a chance to use it). The supplied linens and especially the bath towels were great. This certainly will be on our list the next time are in VT.

HAVRE DE PAIX cottage on Mont Owl's Head slopes
This spot is amazing and we will probably book again next year.

Chalet Chïc Shack
Maxime was so nice and very quick to reply when we had a question. I was not expecting neighbours so close to the patio and the spa so there was not a lot of privacy when we were sitting outside.

Cozy Country Apartment with private hot tub
Steve's place was great! Reasonably close to Stowe, easy to check in and out, and as described in the listing.

Ruiter Brook House
We stayed at Yohanns as a base for skiing at Jay Peak and Sutton. Everything was great. Comfortable beds, hot shower, lovely setting, great hot tub. The local villages are limited in terms of dining options but the kitchen is well set up for cooking etc… Would certainly stay again.
Family- and pet-friendly home rentals

Private & Intimate Cottage In Eastern Townships
very nice experience at the cottage - kids liked it and we had lots of games and puzzles to do on a rainy day. interior stair will be remebered :) saw lots of deer and two wild turkeys every day on the gravel road to keep in mind when driving. ski is few minutes alway with a car. most of the close by restaurants (30min away) open after thursdays, so we were goint at the owls head hotel restaurant- not bad but need reservation on a busy days. overall excelent 5 day ski vacation. kuddos to the owner.

2 bedroom cottage at Stony Brook Farm- Stowe area
This place was such a great reset from a stressful job. My elderly aunt was easily able to move about the cottage (no steps) and the way the rooms are set up makes the small space feel spacious. There is a deck off the back of the house that overlooks a field (full of what we decided are buttercups) that their goats and horse would graze there. We at breakfast our there both mornings. Really beautiful chickens walking around the property clucking happily. Everything we needed was provided, it was a really nice experience. (There was a pack’n’play and high chair and toys and books for young children. We were both sorry we couldn’t stay longer. Definitely recommend!

Secluded Paradise on the Connecticut River, VT
beautiful property. very private. our dog really enjoyed. the patio had swings with the river view it was gorgeous.

ON THE 3RD
We had a super stay! The house is very well laid out and everything was there for us!!

Pine Cabin, Galusha Hill Farm, incredible view!
We loved our stay and hope to come back again!

Owls Head
My boyfriend and I stayed at the Owl's Head Cabin for a long weekend skiing at Jay. The cabin is small and cozy, very warm, and the right size for two people for a weekend. In addition to the main bed, there's a loft with a sleeping area, but you'd have to be very small to get into it and enjoy it; I'd guess the cabin would be a bit small for a couple with children but maybe if you're out all day it'd be okay. Cooking appliances worked well. The one note of caution is that you have to drive on a somewhat rough, uphill dirt road for at least 3 or 4 miles to reach the cabin. We fortunately did not have to drive during a time when there was actively snow falling on the road, but the 2wd sedan we rented definitely would not have made it in those conditions; it was a little harrowing even with just the slush and ruts left after plowing. So be careful if your trip coincides with nastier weather! Jason was very communicative and left clear instructions. Overall, we had a lovely stay.

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.

Peaceful Log Cabin in the Woods
Can’t say enough how wonderful our stay at this adorable cabin was. We had the most relaxing, peaceful weekend spent close to nature. Highlight was the little frog pond on the property which made for some fantastic frog watching. Emily’s cabin has absolutely everything you could ever ask of an airbnb. Can’t wait to book again someday!
Family-friendly home rentals with a pool

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!

Cozy two-bedroom cabin near Smugglers Notch
We could not have asked for a better place for our eclipse adventure. The two bedroom cabin was spotlessly clean, well-appointed, cute and plenty of space for the 4 of us. We loved being out in the woods and enjoyed our walks around the pond enormously. Easy to get to restaurants and other activities, but away from the hustle and bustle. The staff were super friendly and very helpful. Not a thing to complain about, and would definitely recommend to anyone!

Hilltop View Lodge - White Mountains, NH
Our stay was wonderful at the cabin. The cabin was clean and centrally located to winter activities. Andrea was very responsive. Cant wait to go back again

Sunset Cottage on the Richelieu River CITQ#302701
We can’t thank Lisa enough for sharing her home with us, even though our stay was fairly short. Lisa was a very gracious host, very responsive, and very friendly. The cottage (and backyard) looks like it’s from a postcard - very picturesque. The surroundings are extremely calm and relaxing. The entire home was well equipped with everything we needed (cleaning supplies, condiments, towels, kitchen utensils etc.) and very clean. The beds were super comfortable and the pillows even better. Also, having the pool clean and the water nice and warm was the cherry on top! We look forward to visiting Lisa’s home again, and fully take in what the area has to offer. Thank you very much Lisa!

Ski in Ski out - fantastic location on the trail
Just awesome. Slopeside access, close to Tram Side and right on Grammy Jay which was easy for the littles to get the day started on the way to the double. When it was cold (once) we used the fireplace and the condo warms up quickly. Plenty of hot water. A near perfect stay. Fantastic!

Secluded Lumberjack Cabin w/ Hot Tub, Pool & Lake
This was such a perfect cabin for a weekend getaway with my husband. it was perfect and we hope to be back again in the near future. thank you f9r sharing this space with us. we loved it

Gorgeous panoramic views - 4 miles to the mountain
Absolutely wonderful stay! As a family of five, we couldn't have asked for a better place. The unit was incredibly spacious, comfortable, and had such a warm, homey feel—it truly felt like a home away from home. The mountain view from the living room window was beautiful, a perfect backdrop for our mornings and evenings. Jeff, the host was exceptional—extremely responsive, thoughtful, and helpful throughout our stay. Every question or request was handled quickly and kindly, which made our experience stress-free and enjoyable. We had some wifi issues which took time to resolve but Jeff helped and made sure it is taken care of. The apartment was impressively well-equipped with everything we needed, clearly a lot of care went into preparing the space for guests. The location was perfect for us— surrounded by beautiful trails that we explored as a family. If you are into skiing, the ski tracks are short drive away. It was the ideal base for both adventure and relaxation. Highly recommended

EPIC Stowe Getaway - Great For Families & Friends
weekend family trip for 6 of us and our dog(4 adults and 2 kids), plenty of space for everyone, and much larger than I expected! we enjoyed cooking in the well stocked kitchen, playing board games on the large dining room table, swimming in the pool and soaking in the hot tub, wrapping the nights up with a movie on their Roku TV! Kristin was very responsive in her communication, we had a lovely time and would love to plan future trips here again!
Quick stats about vacation rentals that are family-friendly in Montgomery
Total rentals
50 properties
Nightly prices starting at
G$27,168 GYD before taxes and fees
Total number of reviews
3K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
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- Jay Peak Resort
- Smugglers' Notch Resort
- Owl's Head
- Mont Sutton Ski Resort
- Ski Bromont
- Parc Safari
- Amazoo Park
- Bolton Valley Resort
- Jay Peak Resort Golf Course
- Spruce Peak
- Sherbrooke Golf Club
- Cochran's Ski Area
- Pump House Indoor Waterpark
- Le Vignoble du Ruisseau - Winery & Cidery
- Country Club of Vermont
- Val Caudalies - Vignoble & Cidrerie
- Vermont National Country Club
- Leahy Center for Lake Champlain
- Ethan Allen Homestead Museum
- Le Club De Golf Memphrémagog
- Domaine Cotes d'Ardoise - Winery & Cidery
- Burlington Country Club
- Pinegrove Country Club