Middletown Vacation Rentals

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Make Middletown your next getaway

Middletown NY

Top Middletown property types

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House rentals

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Studios

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Popular amenities for Middletown vacation rentals

Popular
Dog-friendly Internet Pool
Cozy Catskills Vacation Rental with Deck!
0 Bedroom | 1 Bath | Sleeps 3

Cozy Catskills Vacation Rental with Deck! - Middletown, NY

$118 avg / night
(excludes fees and taxes)
Catskills Mountain Casita: Ski, Hike, Fish & Golf!
3 Bedroom | 2 Bath | Sleeps 10

Catskills Mountain Casita: Ski, Hike, Fish & Golf! - Middletown, NY

$224 avg / night
(excludes fees and taxes)
5.0 (3)
'Bearpen Lodge' on 125 Acres - Near Belleayre Mtn!
3 Bedroom | 2 Bath | Sleeps 8

'Bearpen Lodge' on 125 Acres - Near Belleayre Mtn! - Middletown, NY

$318 avg / night
(excludes fees and taxes)
5.0 (8)
Brushridge Mountain House: Ski, Hike & Fish
3 Bedroom | 2.5 Bath | Sleeps 8

Brushridge Mountain House: Ski, Hike & Fish - Middletown, NY

$323 avg / night
(excludes fees and taxes)
5.0 (1)
Walk to Vly Creek: Catskills Getaway w/ Porch
4 Bedroom | 1.5 Bath | Sleeps 8

Walk to Vly Creek: Catskills Getaway w/ Porch - Middletown, NY

$211 avg / night
(excludes fees and taxes)

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Recent Middletown guest reviews

This house was even more beautiful, clean, and comfortable than we could have imagined. We were so happy to have found this gem to stay in to attend our nephew's nearby wedding. Everything is there for a guest to use and you have thought of the tiniest details that anyone needs in a house that is not their own. The decor is beautiful, the views are beyond amazing and having thermostats in every room was terrific for those who like different temperatures in order to sleep well. We were 4 adults (40's, 50's & 60's) and we all wished we lived in a house this gorgeous. Two nights of peace and serenity was perfect and we all hope to be back someday. I've already told others about this beautiful house ~ especially our friends who ski. We all loved staring at those slopes from the living room and balcony ~ it was truly gorgeous.
Jane . | Nov 2025
We had a wonderful Columbus Day weekend. The home was comfortable & cozy. Had everything we needed. Gracious Host. Beautiful setting. 👍😍
Edna . | Oct 2025
Bearpen lodge was exactly what we needed! The house is immaculate and has everything you need. The views are breathtaking in every direction. It is such a quiet, serene comfortable place to be. We didn’t want to leave a we will definitely be back. Adina is amazing….very kind and responsive. If you need to step away from the noise of everyday life, this is the place!
Jennifer . | Sep 2025
Middletown vacation rental FAQ

Yes. 14 of our Middletown vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Middletown vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Middletown team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Middletown, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning