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Kid-friendly holiday rentals in Middlesex

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Middlesex family-friendly rentals

Kid-friendly house rentals

Guest favourite
Home in Waterbury Center
4.98 out of 5 average rating, 121 reviews

Cozy Farmhouse Nestled Between Stowe and Waterbury

LukeRating, 5 stars1 month ago
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.
Guest favourite
Home in Stowe
4.92 out of 5 average rating, 106 reviews

Brand new Beautiful Modern Clean Home On River

DoriceRating, 5 stars2 months ago
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.
Top guest favourite
Home in Tunbridge
4.97 out of 5 average rating, 392 reviews

The Barnbrook House

PeterRating, 5 stars5 days ago
The Barnbrook House was like something from a fairytale. It was more spacious than we thought looking at the photos. I loved my stay here, Dana was very communicative and timely. The fireplace was a great feature of the accommodation which we made good use of. I liked how there was an off grid vibe without actually being too far away from modern conveniences like Wifi, TV, AC. I would stay here again.
Top guest favourite
Home in Waterbury Center
4.97 out of 5 average rating, 197 reviews

Vermont Getaway Home - Perfect Location

DaraRating, 5 stars3 weeks ago
The place was very clean and comfortable. Mary-Ellen is easy to work with. Very comfortable-we enjoyed our stay.
Guest favourite
Home in Montpelier
4.94 out of 5 average rating, 372 reviews

Modern not so tiny house

VickyRating, 5 stars1 week ago
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!
Top guest favourite
Home in Moretown
4.98 out of 5 average rating, 116 reviews

Cozy Vermont Cabin | Ski, Hike & Chef’s Kitchen

CarolRating, 5 stars1 month ago
The pictures on the site represent 100% and more! We arrived close to midnight in complete darkness only to wake with the peaceful sounds of nature, surrounded by majestic trees and lush northern foliage. My only regret was that I had to rush back home and not have more time to explore the area. Don’t pass up on an opportunity to stay at Raquel’s gorgeous, warm and inviting woodland cabin, unless you prefer hotel powdered eggs 🤣
Guest favourite
Home in Waterbury Center
4.95 out of 5 average rating, 132 reviews

Peaceful setting with Mountain Views

HallieRating, 5 stars3 months ago
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 :)
Top guest favourite
Home in Montpelier
4.97 out of 5 average rating, 325 reviews

Cozy, sunny apt. in Montpelier, Vt.

LexieRating, 5 stars2 weeks ago
We stayed two nights and wish we had more time. The space is beautiful with really nice decor and the plants are amazing company! Spacious apartment with anything you could need for a relaxing stay. All of the instructions were clear and the hosts even allowed us to check in early! Walking distance to downtown and close to our local family and friends. We’ll definitely be back.

Family-friendly apartment rentals

Superhost
Flat in Northfield
4.84 out of 5 average rating, 110 reviews

River's Bend NEW 1-bd Apt - 8 Mins to Montpelier

NikolasRating, 5 stars2 weeks ago
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.
Superhost
Flat in Barre
4.85 out of 5 average rating, 186 reviews

Studio suite in Barre

CrystalRating, 5 stars1 month ago
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!!
Guest favourite
Flat in Stowe
4.87 out of 5 average rating, 158 reviews

The Nest in Stowe

KeriRating, 5 stars7 months ago
Bottom line: I would stay here again. The place is cozy and tidy. Carmin made obvious efforts to make the place welcoming. It’s a good location that’s removed from the congestion of the village center, but you can get there by car in 5 minutes. You can walk out the door and go for a hike. Water pressure in the shower is good. Carmin provides lots of local recommendations. Netflix readily available. Coffee and welcome snacks given. Heater heats up place quickly. If you’re a light sleeper, bring ear plugs as you can hear any car pass at night. The place is older, and as such has houseflies. They’re being managed, but it’s a little surprising at first. The place is clean. I didn’t find vent fans for the kitchen or bathroom, but there are windows close. The bed is fairly comfortable, on the softer side, but the pillows are noisy. The cookware is a little beat up (missing handles), but functional. We did not use the washer or dryer. Overall good stay.
Guest favourite
Flat in Bristol
4.86 out of 5 average rating, 155 reviews

Overlook at the Office

JillRating, 5 stars4 days ago
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.
Top guest favourite
Flat in Waterbury
4.94 out of 5 average rating, 205 reviews

1880 Purple Village Victorian

GayleRating, 5 stars2 weeks ago
While talking with her, we discovered that my mother was her 2nd grade teacher. Georgeanne was fantastic about giving us our privacy. Our time in her home was very restful and quiet.
Guest favourite
Flat in Montpelier
4.88 out of 5 average rating, 704 reviews

Entire 2nd Floor Walk to Montpelier

CheriRating, 5 stars4 days ago
Will and Patti responded to questions quickly. The apartment was in a great location. We were able to walk to many Montpelier shops and restaurants. The apartment was very comfortable, with old Vermont charm. It had off street parking, a/c (minisplits) for the hot days and windows/screens for the cooler days. We would definitely stay here again!
Top guest favourite
Flat in Waterbury
4.94 out of 5 average rating, 377 reviews

Beautiful Victorian

ChrisRating, 5 stars5 days ago
Pleasure staying at your place as always. Best of luck to you!
Guest favourite
Flat in Waitsfield
4.93 out of 5 average rating, 213 reviews

Historic District Overlooking the Mad River Studio

ChrisRating, 5 stars2 weeks ago
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!

Family-friendly apartment rentals

Superhost
Apartment in Stowe
4.84 out of 5 average rating, 108 reviews

Entire rental unit sleeps up to 6

DanielleRating, 5 stars1 day ago
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!
Guest favourite
Apartment in Stowe
4.93 out of 5 average rating, 168 reviews

Black Bear's Den in Historic Stowe Center

SaraRating, 5 stars1 month ago
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!
Guest favourite
Apartment in Brownington
4.94 out of 5 average rating, 321 reviews

Faraway Acres. Enjoy country living at it's best!

LydiaRating, 5 stars6 days ago
We had a great 1-night stay! The place is very well stocked for short stays, even with an electric two burner cook top, microwave and fridge. Lots of linens and cutlery and cooking utensils and pots and pans. Super clean and more spacious than I was expecting. If you’re lucky you will meet the pups! I hope to come back!
Guest favourite
Apartment in Cambridge
4.94 out of 5 average rating, 154 reviews

Lovely Ski-in / Ski-out Studio at “Smuggs”⭐️

KatherineRating, 5 stars2 months ago
Absolutely love smuggler's notch resort and James was a very good host. Everything went smooth and the condo was perfect.
Top guest favourite
Apartment in Stowe
4.97 out of 5 average rating, 115 reviews

Renovated 4-bedroom House: Hot Tub & Outdoor Space

ToskaRating, 5 stars1 month ago
The condo was excelent. Plenty of space, clean, and well organized. The condo has lots of dishes, pots, pans, cups which made it easy to cook. The grill was in good condition and located perfectly on the balcony. Josh was very responsive and flexible. He gave very clear instructions and the expectations for checkout were very reasonable and easy to complete. Great place to book if you are bringing children and pets! Plenty of yard space for them to play. The location is a close to drive stowe for skiing and to ben and jerrys factory for a fun family acitivty. I highly recommend this location!!
Top guest favourite
Apartment in Waterbury
4.98 out of 5 average rating, 179 reviews

Luxury Treetop Vacation Home in Waterbury Center

Kyra And AdamRating, 5 stars2 months ago
We had a fabulous stay at Chris and Annie's condo in Waterbury. It's a very large and comfortable condo, incredibly clean and tastefully appointed with comfortable beds and linens. Loved the flesh flowers in each room and the Heady Topper in the fridge! Very convenient for skiing and exploring Sugarbush and Stowe. Chris was very easy to communicate with prior to our stay and was kind enough to check in to see that we'd arrived safely. Would highly recommend to anyone looking for a place in Waterbury!
Guest favourite
Apartment in Cambridge
4.92 out of 5 average rating, 115 reviews

Family Friendly Large Condo at Smuggler Notch

JaimeRating, 5 stars5 days ago
Roxy was very responsive. very easy self check in. Great location in Smugglers Notch. loved that the kitchen was fully stocked!
Guest favourite
Apartment in Warren
4.82 out of 5 average rating, 112 reviews

Modest Mountain Dacha

JoanneRating, 5 stars4 months ago
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.

Quick stats about holiday rentals that are kid-friendly in Middlesex

  • Total rentals

    30 properties

  • Nightly prices starting at

    ₹6,025 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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