Family-friendly holiday rentals in Middletown
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Middletown
Guests agree: these family-friendly homes 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 Middletown family-friendly rentals
Family-friendly home rentals with a hot tub
Guest suite in Mansfield
4.95 out of 5 average rating, 193 reviewsCozy private apt 8 mins from UCONN - solar powered
11–18 Sep
Home in Goshen
4.9 out of 5 average rating, 48 reviewsCharming renovated farmhouse with hot-tub
28 Nov – 5 Dec
Home in Ashford
4.9 out of 5 average rating, 71 reviewsLarge secluded house in the Woods! Bonfires, hikes
18–25 Nov
Home in Milford
5.0 out of 5 average rating, 84 reviewsDirect Waterfront-Best location in Milford-Hot Tub
7–14 Sep
Villa in Guilford
4.91 out of 5 average rating, 11 reviewsPrivate Luxury Waterfront Home
9–16 Apr
Home in New Haven
4.79 out of 5 average rating, 38 reviewsBeautiful barn in New Haven with a hot tub!
8–15 Aug
Flat in Shelton
4.69 out of 5 average rating, 315 reviews1ST FLR APT Your private resort, now FAMILY-ized!
25 Nov – 2 Dec
Flat in New Haven
4.75 out of 5 average rating, 126 reviewsLuxury Penthouse Minutes to Yale
11–18 Aug
Family- and pet-friendly home rentals
Home in East Haven
4.88 out of 5 average rating, 196 reviewsBeach Cottage by the Sea
14–21 Nov
Cabin in Coventry
4.83 out of 5 average rating, 122 reviewsLake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
18–25 Sep
Cottage in Guilford
4.93 out of 5 average rating, 245 reviewsCharm + location. Walk to beach, town, & harbor.
16–23 Dec
Cottage in Branford
4.85 out of 5 average rating, 197 reviewsCozy Home In Short Beach Community
30 Nov – 7 Dec
Flat in Milford
4.89 out of 5 average rating, 238 reviewsThe Farmhouse Estate Apartment
19–26 Oct
Home in East Lyme
4.77 out of 5 average rating, 135 reviewsCharming Black Pt beach house. 2 blocks beach.
17–24 May
Cottage in East Haddam
4.93 out of 5 average rating, 86 reviewsCottage on the hill
19–26 Jun
Flat in Branford
5.0 out of 5 average rating, 69 reviewsTree Fort Suite at Stony Creek Depot
14–21 Feb
Family-friendly home rentals with a pool
Home in Montville
4.91 out of 5 average rating, 234 reviewsCasino Wine Down House***
9–16 Sep
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12–19 Sep
Cottage in Litchfield
4.98 out of 5 average rating, 65 reviewsCottage on Litchfield Farm
21–28 Dec
Home in Fairfield
4.62 out of 5 average rating, 29 reviewsModern artist retreat near beach
26 Oct – 2 Nov
Home in Monroe
4.97 out of 5 average rating, 184 reviewsGarden Level Suite with Beautiful Pool
5–12 Apr
Flat in Old Saybrook
4.99 out of 5 average rating, 111 reviewsConvenient and Cute in Downtown Old Saybrook
17–24 Oct
Guest suite in Guilford
4.96 out of 5 average rating, 151 reviewsBright, Cozy Apartment in Guilford
10–17 Jul
Home in Windham
4.96 out of 5 average rating, 138 reviewsMid Century Ranch House on Farmland
31 Dec – 7 Jan
Quick stats about holiday rentals that are family-friendly in Middletown
Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
2.2K reviews
Nightly prices starting at
€ 93 before taxes and fees
Destinations to explore
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