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
16–23 May
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12–19 Sep
Home in Middletown
4.95 out of 5 average rating, 19 reviewsHot Tub and pool Home away from home
28 Nov – 5 Dec
Home in East Hampton
4.92 out of 5 average rating, 38 reviewsCountry house getaway for relaxing & fun!
6–13 Dec
Home in Wallingford
4.91 out of 5 average rating, 23 reviewsSpacious 4Bd/2Ba Family Friendly Home. Sleeps 10
15–22 Apr
Home in Montville
4.98 out of 5 average rating, 61 reviewsHot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos
5–12 Mar
Home in Wolcott
4.95 out of 5 average rating, 19 reviewsAmazing GParadise w/King Bed, Private Pool and BBQ
13–20 Feb
Home in East Haddam
5.0 out of 5 average rating, 11 reviews5 Bedroom Country Home w. Private Pool!
10–17 Apr
Weekly house rentals
Home in Coventry
5.0 out of 5 average rating, 105 reviewsWaterfront 10 min to Uconn outdoor tv gas fire pit
27 Jan – 3 Feb
Home in Haddam
5.0 out of 5 average rating, 78 reviewsCozy Comforts!
20–27 Aug
Home in Middletown
5.0 out of 5 average rating, 12 reviewsHome with Fiber Optic Internet
25 Sep – 2 Oct
Home in Middletown
4.97 out of 5 average rating, 38 reviewsHome away from home
5–12 Aug
Home in Glastonbury
4.8 out of 5 average rating, 49 reviewsIdyllic Ranch, Centrally Located
17–24 Mar
Home in Southington
4.96 out of 5 average rating, 72 reviewsConnecticut Chalet - Private Pond, Firepit, Views!
22–29 Oct
Home in Southington
4.88 out of 5 average rating, 16 reviewsLarge 2nd floor of duplex in town center
24–31 Aug
Home in Haddam
5.0 out of 5 average rating, 9 reviewsThe Farmhouse Stay
5–12 Oct
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 Oct
Home in Southbury
5.0 out of 5 average rating, 57 reviewsThe Cottage at Cedar Spring Farm
29 Aug – 5 Sep
Home in East Haddam
4.95 out of 5 average rating, 93 reviewsRomantic Getaway at The Lake!
10–17 Oct
Home in Bristol
4.84 out of 5 average rating, 32 reviewsCute Cape Near the Park w/ Gameroom!
25 Nov – 2 Dec
Home in East Hampton
4.99 out of 5 average rating, 92 reviewsClassic Lake House~4 Steps to water_FirePit_kayaks
15–22 Apr
Home in Glastonbury
5.0 out of 5 average rating, 37 reviewsGlastonbury home, Large Porch, Peloton & Pets OK
25 Sep – 2 Oct
Home in West Hartford
5.0 out of 5 average rating, 17 reviewsThe little house that could!
25 Sep – 2 Oct
Home in South Windsor
4.86 out of 5 average rating, 21 reviewsGrampa Potatoes Homestead
25 Aug – 1 Sep
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
1.4K reviews
Nightly prices starting at
€ 28 before taxes and fees
Destinations to explore
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