On the Edge of Nature
4 guests
3 bedrooms
Gardiner, New York
It’s the end of the line. Beyond this chalet, there’s nothing but Minnewaska’s protected preserveland.
Middletown Resorts
We selected the 942 homes worth renting in this location
Home spotlights in Middletown
Rise with the Sun
20 guests
8 bedrooms
Pleasant Valley, New York
Nestled within 26 acres of beautiful grounds, this private estate welcomes you to an immersive retreat in Rhinebeck. From the indoor sauna and hot tub to the calm rooms, every detail has been considered to inspire optimum relaxation.
The Great Frontier
4 guests
1 bedrooms
Chatham, New York
Reminiscent of something from a Laura Ingalls Wilder novel, this picturesque cabin is a haven surrounded by peace and quiet and lush woodland. Although you can count on a serene stay here, you’re also just a five-minute drive from the quaint town of Old Chatham where you can find some local amenities, or a ten-minute drive from Chatham Town, which has several excellent restaurants and plenty of charming local shops.
A Summer's Eve
15 guests
7 bedrooms
Greenburgh, Westchester County
If you need a base for a friendly get-together or a family reunion, then look no further than this abode in the heart of Westchester County. Thanks to the games room, gym and cinema room, there’s never a dull moment here – and that’s just what’s inside the home.
We selected the top 3% holiday homes in Middletown Resorts
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Frequently asked questions
Find homes in Middletown with all the luxuries of a resort. Each and every one of our vacation rentals is obsessively checked by our experts, and comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. A stay in one of our homes in Middletown that brings a resort vacation to mind is a stay that guarantees quality, so book your getaway today. And of course, feel free to reach out to our expert team, on hand to assist you 24/7.
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