Middletown cottage rentals
We found 147 cottage rentals — enter your dates for availability
Explore Middletown cottage rentals
Hello Small Stone
Sleeps 4 · 2 bedrooms · 2 bathrooms
Cozy Haven: A Romantic Retreat in our Tiny House!
Sleeps 2 · 1 bedroom · 1 bathroom
Huguenot Retreat w/ Screened Porch & Lake Access!
Sleeps 8 · 3 bedrooms · 1 bathroom
Secluded Cabin in the Southern Catskills Less than 2 Hours from NYC
Sleeps 4 · 2 bedrooms · 1 bathroom
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Sleeps 5 · 2 bedrooms · 1 bathroom
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Sleeps 4 · 1 bedroom · 1 bathroom
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value