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
19–26 Sept
Cabin in Colebrook
4.94 out of 5 average rating, 197 reviewsAdorable, storybook log cabin
24–31 Jan
Home in Goshen
4.9 out of 5 average rating, 48 reviewsCharming renovated farmhouse with hot-tub
30 Nov – 7 Dec
Home in Ashford
4.9 out of 5 average rating, 71 reviewsLarge secluded house in the Woods! Bonfires, hikes
27 Aug – 3 Sept
Home in Branford
4.95 out of 5 average rating, 55 reviewsAmazing Waterfront, Private Beach + Hot Tub
4–11 Oct
Villa in Guilford
4.91 out of 5 average rating, 11 reviewsPrivate Luxury Waterfront Home
12–19 Mar
Home in New Haven
4.79 out of 5 average rating, 38 reviewsBeautiful barn in New Haven with a hot tub!
10–17 Aug
Flat in Shelton
4.69 out of 5 average rating, 316 reviews1ST FLR APT Your private resort, now FAMILY-ized!
27 Nov – 4 Dec
Family- and pet-friendly home rentals
Cabin in Coventry
4.83 out of 5 average rating, 122 reviewsLake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
6–13 Jan
Cottage in Guilford
4.93 out of 5 average rating, 245 reviewsCharm + location. Walk to beach, town, & harbor.
8–15 Oct
Cottage in Branford
4.85 out of 5 average rating, 197 reviewsCozy Home In Short Beach Community
30 Nov – 7 Dec
Guest suite in Greenport
4.94 out of 5 average rating, 141 reviewsGREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH
20–27 Nov
Flat in Milford
4.89 out of 5 average rating, 238 reviewsThe Farmhouse Estate Apartment
28 Dec – 4 Jan
Home in East Lyme
4.77 out of 5 average rating, 135 reviewsCharming Black Pt beach house. 2 blocks beach.
8–15 Oct
Cottage in East Haddam
4.93 out of 5 average rating, 86 reviewsCottage on the hill
21–28 Jun
Flat in Branford
5.0 out of 5 average rating, 70 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***
25 Jun – 2 Jul
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12–19 Sept
Home in East Marion
4.95 out of 5 average rating, 104 reviews* Restored Farmhouse on the North Fork
3–10 Jun
Cottage in Litchfield
4.98 out of 5 average rating, 65 reviewsCottage on Litchfield Farm
23–30 Dec
Home in Fairfield
4.62 out of 5 average rating, 29 reviewsModern artist retreat near beach
6–13 Aug
Home in Greenport
New place to stayQuaint Chalet w/Salt-heated Pool
5–12 Nov
Home in Monroe
4.97 out of 5 average rating, 184 reviewsGarden Level Suite with Beautiful Pool
6–13 Sept
Flat in Old Saybrook
4.99 out of 5 average rating, 111 reviewsConvenient and Cute in Downtown Old Saybrook
19–26 Oct
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
£80 before taxes and fees
Destinations to explore
- New City Holiday rentals
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