
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

Quiet neighborhood oasis
This was our first stay in the Leonard Ave location. Kevin met us at the house and showed us everything. There were a few items that were needed and Kevin took care of those immediately. His communication was excellent and we enjoyed our stay. There were 9 of us and the accommodations were exactly what we needed! We will absolutely book again!

Lake Dunmore Home close to skiing & Middlebury
Perfect getaway for our family of 6. It was cold and rainy but plenty to do at the house. Kids loved the game room. We got to take a freezing cold dip in the lake and warm up in the hot tub. Thanks for having us!!!

Duplex in Lyndon - Ground Floor Unit
This is our third experience at Amanda’s Airbnb. As always it’s a cute, beautiful, and clean place. Great location for our pets to be able to run around. Looking forward to staying here again!

Morrisville's Cottage Style Coziness
Sherry's cottage was the perfect place for our family to view the eclipse from! The place was well-equipped with everything we needed and spotless. Would definitely stay again!

Gorgeous 1835 Farmhouse w. Lake/MTN Views!
It is a beautiful house where you can smell the family and we liked that a lot. It is close to the ski slopes, very clean and comfortable. Lidsa and Tom have very good communication, excellent service.

The McKinley House
We had a great stay, lovely welcoming home and great location - short walking distance to nice places in town and 30min drive to either Sugarbush or Killington/Pico. Thank you!

Quiet lakeside retreat with private dock.
This is a lovely place for a get-away time. It's very comfortably furnished, spotless, and in a beautiful area. The kitchen is one of the most adequately equipped of any Airbnb place we have stayed in. The hosts are super responsive and helpful!

Lakefront Peaceful Getaway in Mountain Lakes
Such a beautiful home & only about 15-30 minutes from tourist locations depending on your plans. Lots of room so everyone is comfortable! We had a great time.
Kid-friendly apartment rentals

Central Lair
I've been to Burlington many times to visit my son and Lori's place is my favorite! So cute and comfy, clean and inviting! The charms of an old house but updated for modern convenience. Her attention to detail is quite evident making our experience even better, things like yummy snacks, chocolate on the bed, water filter in the fridge, great towels. I loved the Zebra kitchen so much! It's in a great location, close to downtown. The stairs to access the apartment are quite steep as she shares in her description, something to keep in mind, but we managed fine. Thank you Lori! We will be back!

Quaint NNE Apartment
Our two night stay at Kent’s was absolutely wonderful! Kent was charming, friendly, and gave us great recommendations for places to eat. The apartment was cozy and welcoming, with great attention to meeting guests’ needs. We could not have asked for a better place to spend the weekend and have every intention of going back again!

New Modern Apartment - Woodstock Village on Mt Peg
Sam is a friendly, generous, helpful host! He and his family live upstairs in this fun, modern building; the apartment is on the ground floor/daylight basement, but the house sits on a steep hill so the unit has plenty of natural light and does not feel like a basement. The separate entrance is located at the far end of the structure so it feels like a standalone unit with plenty of privacy. The neighborhood rises steeply from downtown Woodstock, up narrow, steep, windy roads. The streets were pretty consistently plowed, but drive slowly and cautiously, especially with snow. Also, like Sam says, don't just enter the address into Google Maps; it will try to take you elsewhere through someone's house and yard (haha!) Instead, follow Sam's directions. We loved the casual, yet carefully curated decor and found the bedroom super cozy with the most comfortable bed and linens. Our favorite was going on a cross-country ski adventure right out the back! Thank you, Sam, for a great stay!

Lake Champlain and Adirondack Views
June’s place is nice and cozy, great amenities including washer/dryer, beautiful views of Lake Champlain and Adirondack mountains. June was a responsive host and helped us get in to her place last minute with ease.

Funky apartment near Lake Champlain
Cozy space, lovely hosts! Our arrival was perfectly timed with a snow storm. Our hosts were kind, flexible, friendly, and very easy to communicate with. The space is warm and colorful, with a nicely functional kitchen. The area is easily walkable from lakeside to Church St shops, even in snow. As others have mentioned, there is a decent amount of sound bleed between the guest and host spaces, but it was not a problem for us. Pretty typical for an older house, and adds to the coziness. :)

South End Arts & Enterprise District 1BR Apartment
We had a great stay! This Airbnb was extremely well stocked. It was so nice to have coffee in the morning with milk and seltzer as options as well. Wes also set up a pack n play for us when he found out we were bringing our son which was very kind. Its a nice quiet neighborhood but very easy to walk wherever we needed to go in Burlington. We would definitely stay here again!

Walk Downtown | Private Balcony | Parking |Netflix
We greatly enjoyed our second stay here in Burlington at Lea’s place! An easy walk into town to explore the area. We will definitely be back again :)

Quiet & Cozy 2bdrm walk anywhere pet friendly
Erinn was fantastic to work with and super responsive. I sent her a few messages and she respond almost immediately. We asked for an early check in and she was very accommodating! Her home was just as described and spotless. There were clear instructions for both check in and check out which made everything very easy. Her place was walkable to downtown and there were several great places to eat that were dog friendly which was a bonus for us. We would definitely stay again and recommend her!!
Kid-friendly condo rentals

Killington Condo-Indoor Pool/HotTub/FitnessCenter
Great place for our ski weekend! Spacious, clean, super comfortable beds, kitchen had everything needed, even spices! close easy drive to slopes! Great host- it was easy to communicate, we felt really welcome in this beautiful place! Would love to come back again and again!

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

Renovated 4-bedroom House: Hot Tub & Outdoor Space
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!!

Family condo ski in/ski out Bolton main lodge!
Great view of the mountains across from the trails! Beautiful sunset from the balcony. Jetted bathtubs were appreciated too!

Renovated Condo(unit #10) 3 Miles from Mtn
We had a great weekend getaway! Close to Sugarbush for skiing, surrounding towns and restaurants! Would highly recommend a stay here.

Family Friendly Large Condo at Smuggler Notch
We had a great stay. The condo is spacious, and the toys were a big hit with the kids. The location is as advertised - right in the heart of Smuggler's Notch and a short walk to the village and Morse Mountain chairlifts. Getting to / from any part of the resort is a breeze with shuttle service available right outside the building. Having access to the unit's ski locker at the ground level is a big help, and there are plenty of coat hangers as well as ample space to store boots, helmets, etc. It's an ideal place and set-up for a Smuggler's notch ski trip.

*Killington Summer Rental: 3 Bdrm, 2 Bth*
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!

Ski, Ride, Walk On/Off Condo On Pico at Killington
Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.
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
- Spruce Peak
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Jay Peak Resort Golf Course
- Cannon Mountain Ski Resort
- Pump House Indoor Waterpark
- Cochran's Ski Area
- Mt. Eustis Ski Hill
- Country Club of Vermont
- Ethan Allen Homestead Museum
- Fort Ticonderoga
- Northeast Slopes Ski Tow
- Dartmouth Skiway
- Killington Adventure Center
- Cozy Cottages & Otter Valley Winery
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Vermont National Country Club
- Leahy Center for Lake Champlain
- Lincoln Peak Vineyard
- Burlington Country Club