Kid-friendly holiday rentals in Middlesex
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Middlesex
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Middlesex family-friendly rentals
Kid-friendly house rentals
Home in Middlesex
4.93 out of 5 average rating, 156 reviewsTrue Mountain House
25 May – 1 Jun
Home in Waterbury Center
4.98 out of 5 average rating, 132 reviewsVermont vacation house
10–17 Jun
Home in Moretown
4.98 out of 5 average rating, 132 reviewsLovely Waterbury Home (Crossroads of Recreation)
19–26 Mar
Home in Montpelier
4.94 out of 5 average rating, 343 reviewsModern not so tiny house
6–13 Feb
Home in Waterbury Center
4.96 out of 5 average rating, 117 reviewsPeaceful setting with Mountain Views
5–12 Jan
Home in Waterbury Center
4.99 out of 5 average rating, 107 reviewsStunning mountain views/Stowe-Waterbury
28 May – 4 Jun
Home in Barre
4.92 out of 5 average rating, 321 reviewsSouth(ern) Comfort
24 Apr – 1 May
Home in Waterbury Center
4.98 out of 5 average rating, 102 reviewsCozy Farmhouse Nestled Between Stowe and Waterbury
19–26 Nov
Family-friendly apartment rentals
Flat in Montpelier
4.89 out of 5 average rating, 112 reviewsThe Studio - in the heart of Montpelier
19–26 Jan
Flat in Waterbury
4.98 out of 5 average rating, 318 reviewsVillage Suite
18–25 Feb
Flat in Montpelier
4.87 out of 5 average rating, 605 reviewsEntire 2nd Floor Walk to Montpelier
29 Nov – 6 Dec
Flat in Waitsfield
4.95 out of 5 average rating, 167 reviewsHistoric District Overlooking the Mad River Studio
15–22 May
Flat in Waterbury
4.78 out of 5 average rating, 156 reviewsModern and Charming Village Apartment
13–20 Mar
Flat in Waterbury
4.9 out of 5 average rating, 308 reviewsWaterbury Village Townhouse
18–25 Feb
Flat in Montpelier
4.89 out of 5 average rating, 257 reviewsSunny, spacious studio apartment in Montpelier, VT
28 Jul – 4 Aug
Flat in Waterbury
4.95 out of 5 average rating, 180 reviews1880 Purple Village Victorian
22–29 Dec
Family-friendly apartment rentals
Apartment in Richmond
4.95 out of 5 average rating, 184 reviewsChic Mountainside Studio at Bolton Valley
19–26 Oct
Apartment in Brownington
4.92 out of 5 average rating, 221 reviewsFaraway Acres. Enjoy country living at it's best!
23–30 Oct
Apartment in Vergennes
4.96 out of 5 average rating, 178 reviewsLittle Brick House Off Main (Apt. B)
6–13 Sep
Apartment in Stowe
4.91 out of 5 average rating, 104 reviewsBlack Bear's Den in Historic Stowe Center
19–26 Mar
Apartment in Waterbury
4.97 out of 5 average rating, 154 reviewsLuxury Treetop Vacation Home in Waterbury Center
26 Sep – 3 Oct
Apartment in Cambridge
4.93 out of 5 average rating, 111 reviewsLovely Ski-in / Ski-out Studio at “Smuggs”⭐️
22–29 Jul
Apartment in Killington
4.95 out of 5 average rating, 131 reviews🎿Cozy Fireplace Condo-Mins. to Everything 🚵
1–8 Sep
Apartment in Warren
4.93 out of 5 average rating, 133 reviewsAnother Day in Paradise at Sugarbush Mountain
29 May – 5 Jun
Quick stats about holiday rentals that are kid-friendly in Middlesex
Total rentals
40 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
3.7K reviews
Nightly prices starting at
$95 SGD before taxes and fees
Destinations to explore
- Sherbrooke Holiday rentals
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- Family-friendly rentals United States
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- Family-friendly rentals Vermont
- Family-friendly rentals Middlesex
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