
Kid-friendly vacation rentals in Middlesex
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Top-rated kid-friendly rentals in Middlesex
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Popular amenities for Middlesex kid-friendly rentals
Kid-friendly house rentals

Full House 3 Bedrooms/3.5 Baths
very nice spacious home for a family visit.

Cozy Farmhouse Nestled Between Stowe and Waterbury
We loved our stay at Tyler's house. It was beautiful, clean, and well equipped with everything we needed to make meals together. We felt right at home and enjoyed all the light coming in through the windows. We would definitely book again when in the area.

Brand new Beautiful Modern Clean Home On River
Homey open concept home where you van listen to the river while you take a dip in the cedar hot tub. I also enjoyed the deep soaking tub, closeness to the Von Trappe Famiky Lodge, and the milk brother for my morning coffee.

Vermont Getaway Home - Perfect Location
We were two couples who came in for two nights to attend a meeting, and to enjoy some hiking and biking in the local area. Mary Ellen's home provided us with a quiet and comfortable place to start and end our days. The kitchen was well equipped for us to prepare meals, and we had plenty of room both on the back patio and the living room area to relax at the end of the day. We can easily recommend this home to others visiting the Waterbury/Stowe area.

Modern not so tiny house
My stay was exactly what I needed. I would actually say the pictures don’t do the space justice! It’s far bigger than depicted in my opinion. I was very comfortable and felt at home when I was there. It was really nice to enjoy walking around Montpelier with Mary Beth’s home as my access point. Very grateful for my stay in this sweet not so tiny home!

Cozy Vermont Cabin | Ski, Hike & Chef’s Kitchen
We loved our stay at Raquel’s! We had a wedding at Bliss Ridge Farm and the Airbnb was in a very convenient location. We liked being close to Waterbury and Waitsfield, which had great restaurant options. Loved being so close to Red Hen Bakery! We appreciated how clean and well equipped the house was. We especially enjoyed the little play area for our baby boy.

Peaceful setting with Mountain Views
Home away from home! Susan was a fantastic host. She was very responsive and communicated quickly. This home was perfect for our group of 6 and it was extremely cozy! This was our first time in Vermont and it definitely exceeded all of our expectations. If you looking for a pleasant place to stay with amazing views, look no further than this adorable Airbnb! We skied in Stowe, toured the Ben and Jerry’s ice cream factory down the road and enjoyed some live music at the ZenBarn. I would highly recommend this property! We hope to visit again soon :)

Lovely Waterbury Home (Crossroads of Recreation)
We could not have been any happier with this place. The listing did not do this place justice. Beds were comfortable, space was generous and kid amenities galore! The front room gets a little bit noisy at night with street traffic (nothing a deep sleeper or a noise machine can’t fix!) but other than that it was a very pleasant stay! I already hope to book again next Memorial Day! Thank you so much
Kid-friendly apartment rentals

River's Bend NEW 1-bd Apt - 8 Mins to Montpelier
Very tranquil place, very clean shower, comfortable bed, great amenities, lots of magazines and easy to use television. Very short distance from Montpelier. Nice bird variety, lovely flowers, you can hear the river from the apartment. Bridge is cool, river bank is fun, chairs outside.

Studio suite in Barre
Bernadette was extremely wonderful to meet!! It was great having her for our host for our stay! The little balcony is wonderful, great kinda private little space to sit & enjoy the weather! everything was great & as described! Only thing that was a bit difficult was the stand up shower is pretty small. It was a bit tight washing up. Other than that even the traffic from the beltline wasn't bad at all!! when your inside with tv on you can hardly hear it!! Thanks so much for being such a wonderful person & host to us! Absolutely would stay again in the future if we ever need to find something!!

Overlook at the Office
Small but has a fully equipped kitchen, other than the only sink is in the bathroom. The sink is big and it worked fine. The park is 1/2 block away and town is 2 blocks. Comfortable bed and quiet at night. Good restaurants and unique shops in town. Lots of nature trails close by. Be mindful of having the key it could be easy to get locked out. We enjoyed our time in the apartment and definitely would recommend it to anyone who wants to visit Bristol. Thanks for sharing your place with us.

Village Oasis 2 -the crossroads of VT
Great stay with Mike and Amy. Perfect location for us craft beer geeks. 5 min walk to Stowe St and Freak Folk, Reservoir, Blackback, Pro Pig, Hen of the Wood, and Salt and Rind. Stowe St Cafe is a nice breakfast spot and a big breakfast at the Stagecoach Inn is across the street.

1 Bedroom apartment. Between Stowe and Waterbury.
We loved Tim’s apartment for our Stowe ski weekend. It was just as described and in a beautiful setting. Tim was also great to communicate with and very accommodating when we had some last minute changes to our plans. Will definitely stay here again on a return trip - highly recommend!

The Hideaway
Great place for a ski vacation. The unit was exceptionally clean and Beverly was extremely responsive and helpful. We would definitely stay here again!

Modern & Charming Waterbury Village Apt - 1
Nice, comfortable, clean space in private location. Close to everything. Easy walk into charming Waterbury, full of restaurants, diners, pubs and more. Plus close to Stowe and lots of other wonderful Vermont destinations. Easy access to I-89. I’d highly recommend this place and would stay again. Jeff and Lisa were proactive in checking in, but we had everything we needed and were very happy.

Historic District Overlooking the Mad River Studio
This was the perfect place for my working-get away weekend. Quiet, picturesque views, great food just a few steps from the door, and the place was immaculate. A great place to come "home" to in the evening. Plus, Kellee was quick to respond when I had questions. Highly recommend!
Kid-friendly condo rentals

Entire rental unit sleeps up to 6
My husband and I stayed in National at 1854 House and we loved it! It was exactly as described, and Sarah was a terrific host. Everything was very clean, she was quick to respond, left detailed instructions about all the unit had to offer, and even gave us some local recommendations. The bed was comfortable, the view was great, and the swing in the living room was a wonderful extra touch. The location was perfect for exploring all of northern Vermont. We couldn’t have asked for a better trip. We would absolutely stay in National again. Definitely recommend!

Black Bear's Den in Historic Stowe Center
Cute little place that was a perfect location for our visit to Stowe. Walkable restaurants and stores and even the places we had to drive weren’t far either. The place was very clean and perfect for our group. Would definitely come again!

Another Day in Paradise at Sugarbush Mountain
What an awesome place!! This is the perfect spot for a great weekend at Sugarbush. I can’t wait to stay here again next year!

Faraway Acres. Enjoy country living at it's best!
Lucy’s farmhouse was tranquil and peaceful. Very clean and well maintained. She was very responsive and friendly and made us feel like home. I would definitely recommend to everyone and will come back again

Luxury Treetop Vacation Home in Waterbury Center
This is the nicest Airbnb I have stayed at. It was peaceful , beautifully decorated but not fussy, and so very well equipped. Even the knife set in the kitchen was outstanding (and actually sharp!). We had everything we needed and more. Chris was an excellent communicator and the perfect host. I hope to stay here again in future.

Family Friendly Large Condo at Smuggler Notch
Roxy was very responsive. very easy self check in. Great location in Smugglers Notch. loved that the kitchen was fully stocked!

Modest Mountain Dacha
Very comfortable stay - convenient to ski wither Sugarbush or Mad River. Philip sent specific instructions for turning the heat up on arrival. It took a little while to warm up, but individual thermostats in LR and BR worked nicely. Local recommendations for restaurants and such were spot on.

Bear Cub Studio on Main St
Want to stay in the heart of the town/Stowe? This is the place! Your own designated parking spot. Very close to many eating/drinking establishments...did I say VERY close? Sure, this may equate to as mentioned low-level early-morning sounds from the Bakery/Cafe below so simply rise and shine or pack accordingly! I didn't mind it at all and even if I did, one bite of their maple syrup croissant and all is forgiven! Affordable and Jesse's refund "peace of mind" policy were surely deal makers. BTW, The Black Cap Coffee & Bakery folks and their offerings rule! Actual DARK ROAST coffee...I made sure to purchase a bag of those beans to take home. The restaurant directly out our bathroom window, Cork, was superb in all aspects. Glad we decided to go there the first night.
Quick stats about vacation rentals that are kid-friendly in Middlesex
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
Total number of reviews
3.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Sugarbush Resort
- Jay Peak Resort
- Smugglers' Notch Resort
- Bolton Valley Resort
- Jay Peak Resort Golf Course
- Spruce Peak
- Pico Mountain Ski Resort
- Dartmouth Skiway
- Cannon Mountain Ski Resort
- Cochran's Ski Area
- Pump House Indoor Waterpark
- Autumn Mountain Winery
- Fort Ticonderoga
- Mt. Eustis Ski Hill
- Country Club of Vermont
- Northeast Slopes Ski Tow
- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Vermont National Country Club
- Burlington Country Club
- Killington Adventure Center
- Lincoln Peak Vineyard
- Montshire Museum of Science
- Lucky Bugger Vineyard & Winery