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
9 – 16 Sept
Cabin in Colebrook
4.94 out of 5 average rating, 197 reviewsAdorable, storybook log cabin
25 Jan – 1 Feb
Home in Goshen
4.9 out of 5 average rating, 48 reviewsCharming renovated farmhouse with hot-tub
30 Dec – 6 Jan
Home in Ashford
4.9 out of 5 average rating, 71 reviewsLarge secluded house in the Woods! Bonfires, hikes
15 – 22 July
Villa in Guilford
4.91 out of 5 average rating, 11 reviewsPrivate Luxury Waterfront Home
5 – 12 Mar
Home in New Haven
4.79 out of 5 average rating, 38 reviewsBeautiful barn in New Haven with a hot tub!
11 – 18 Aug
Home in East Lyme
4.9 out of 5 average rating, 42 reviewsDowntown Niantic Home with Hot Tub.
30 July – 6 Aug
Apartment in New Haven
4.75 out of 5 average rating, 126 reviewsLuxury Penthouse Minutes to Yale
25 Nov – 2 Dec
Family- and pet-friendly home rentals
Home in East Haven
4.88 out of 5 average rating, 196 reviewsBeach Cottage by the Sea
27 Mar – 3 Apr
Guest suite in Fairfield
4.94 out of 5 average rating, 361 reviewsPrivate Studio Apartment; Kitchen; Fully Furnished
21 – 28 Mar
Guest suite in Goshen
4.75 out of 5 average rating, 215 reviewsRural Litchfield County Apartment Goshen CT
17 – 24 Apr
Cabin in Coventry
4.83 out of 5 average rating, 122 reviewsLake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
11 – 18 Mar
Cottage in Guilford
4.93 out of 5 average rating, 245 reviewsCharm + location. Walk to beach, town, & harbor.
29 Jan – 5 Feb
Home in Fairfield
4.96 out of 5 average rating, 290 reviewsLuxurious Barn With New England Charm
1 – 8 Dec
Cottage in Branford
4.85 out of 5 average rating, 197 reviewsCozy Home In Short Beach Community
19 – 26 Dec
Guest suite in Greenport
4.94 out of 5 average rating, 141 reviewsGREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH
26 Mar – 2 Apr
Family-friendly home rentals with a pool
Home in Montville
4.91 out of 5 average rating, 234 reviewsCasino Wine Down House***
25 June – 2 July
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12 – 19 Sept
Cottage in Litchfield
4.98 out of 5 average rating, 65 reviewsCottage on Litchfield Farm
24 – 31 Dec
Home in Washington
5.0 out of 5 average rating, 9 reviewsPoshPadsCT "Senff 8-BR" Pool Trampoline 5*Lux Town
18 – 25 May
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
18 – 25 Jan
Home in Fairfield
4.62 out of 5 average rating, 29 reviewsModern artist retreat near beach
27 Nov – 4 Dec
Home in Greenport
New place to stayQuaint Chalet w/Salt-heated Pool
28 May – 4 June
Home in Monroe
4.97 out of 5 average rating, 184 reviewsGarden Level Suite with Beautiful Pool
3 – 10 Sept
Quick stats about holiday rentals that are family-friendly in Middletown
Total rentals
30 properties
Wi-Fi availability
30 properties include access to Wi-Fi
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
$152 AUD before taxes and fees
Destinations to explore
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