A forested landscape with a winding dirt road and power lines.

Middletown houses

We found 679 houses — enter your dates for availability

Explore Middletown house rentals

Image of #24 Serenity A Lakefront Cottage Retreat

Premier Host

#24 Serenity A Lakefront Cottage Retreat

Sleeps 4 · 2 bedrooms · 1 bathroom

Image of Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Sleeps 6 · 3 bedrooms · 3+ bathrooms

Image of Lovely Family sized 3 bedroom Colonial home, close to restaurant.

Lovely Family sized 3 bedroom Colonial home, close to restaurant.

Sleeps 6 · 3 bedrooms · 2 bathrooms

Image of Family Stays: Middletown, CT

Premier Host

Family Stays: Middletown, CT

Sleeps 8 · 4 bedrooms · 2 bathrooms

Image of Historic Home 3 Mi to Middletown Main Street

Historic Home 3 Mi to Middletown Main Street

Sleeps 12 · 6 bedrooms · 2+ bathrooms

Image of Cozy newly remodeled home close to major amenities in Connecticut a

Cozy newly remodeled home close to major amenities in Connecticut a

Sleeps 6 · 3 bedrooms · 1 bathroom

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