House holiday rentals in Middletown
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Top-rated house rentals in Middletown
Guests agree: these houses 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 house rentals in Middletown
House rentals with a pool
Home in Montville
4.96 out of 5 average rating, 106 reviewsCasino Stay & Play House
3–10 Jun
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12–19 Sep
Home in East Marion
4.95 out of 5 average rating, 104 reviews* Restored Farmhouse on the North Fork
3–10 Jun
Home in Middletown
4.95 out of 5 average rating, 19 reviewsHot Tub and pool Home away from home
31 Jul – 7 Aug
Home in East Hampton
4.92 out of 5 average rating, 38 reviewsCountry house getaway for relaxing & fun!
8–15 Jan
Home in Wallingford
4.91 out of 5 average rating, 23 reviewsPrivate 4Bd/2Ba Family Friendly Home. Sleeps 10
20–27 Dec
Home in Old Saybrook
5.0 out of 5 average rating, 24 reviews3BR Private Cottage w/ Pool in Old Saybrook
28 Feb – 7 Mar
Home in East Haddam
5.0 out of 5 average rating, 11 reviews5 Bedroom Country Home w. Private Pool!
12–19 Apr
Weekly house rentals
Home in Southington
4.85 out of 5 average rating, 105 reviews#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
26 Aug – 2 Sep
Home in New Haven
4.99 out of 5 average rating, 189 reviewsQ River House - 2 bdrm, minutes from Yale/Downtown
12–19 Jan
Home in Haddam
5.0 out of 5 average rating, 78 reviewsCozy Comforts!
14–21 Aug
Home in Middletown
5.0 out of 5 average rating, 12 reviewsHome with Fiber Optic Internet
12–19 Oct
Home in Middletown
4.97 out of 5 average rating, 39 reviewsHome away from home
5–12 Aug
Home in Glastonbury
4.8 out of 5 average rating, 51 reviewsIdyllic Ranch, Centrally Located
6–13 Jan
Home in Southington
4.96 out of 5 average rating, 72 reviewsConnecticut Chalet - Private Pond, Firepit, Views!
14–21 Sep
Home in Southington
4.88 out of 5 average rating, 16 reviewsLarge 2nd floor of duplex in town center
26 Aug – 2 Sep
Private house rentals
Home in East Hampton
4.98 out of 5 average rating, 51 reviewsLake Fun: PingPong, Pool Table, Slide, EV Charger
7–14 Jan
Home in East Hampton
4.95 out of 5 average rating, 21 reviewsWaterfront Lake House
16–23 Feb
Home in Southbury
5.0 out of 5 average rating, 57 reviewsThe Cottage at Cedar Spring Farm
20–27 Oct
Home in East Haddam
4.95 out of 5 average rating, 96 reviewsRomantic Getaway at The Lake!
5–12 Oct
Home in Bristol
4.84 out of 5 average rating, 32 reviewsCute Cape Near the Park w/ Gameroom!
13–20 Dec
Home in Wallingford
5.0 out of 5 average rating, 22 reviewsNew England Charmer
17–24 Aug
Home in Bristol
4.98 out of 5 average rating, 57 reviewsRemodeled Historic Forestville Home w/fire pit
1–8 Jun
Home in West Hartford
5.0 out of 5 average rating, 17 reviewsThe little house that could!
8–15 Jan
Quick stats about house rentals in Middletown
Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.4T reviews
Nightly prices starting at
₹2,502 before taxes and fees
Destinations to explore
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- Rentals with a patio Middletown
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