Which Way The River
11 guests
4 bedrooms
Shandaken, New York
Have you ever wanted your very own slice of the Catskills? Of course, you have.
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Old Macdonald
5 guests
2 bedrooms
Stamford, New York
Once an 1890s carriage house, this home has been designed for country living for a small family. Low timber ceilings and hardwood floors retain the barn-like element, but instead of hay bales, you’ve got comfortable king-size beds for grown-ups and secret sleeping spots for kids in the mezzanine above the loft.
The Creekside Cabin
2 guests
1 bedrooms
Jewett, New York
Sitting alongside an enchanting creek, this cabin is a tranquil haven with a lot to offer. From the hot tub and wood fired sauna to the beautiful views, this is the perfect setting for a refreshing and romantic retreat.
The Edge
6 guests
3 bedrooms
Ulster County, Rochester
This NYT-featured Catskills home is not quite the cabin it seems to be. What looks like a single storey home from one angle is actually built over a creekside slope, and we think it's one of the most interesting places we've seen for a peaceful stay in the woods.
We selected the top 3% holiday homes in Middletown Vacation Rentals for Winter
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Browse our remarkable collection of luxury Vacation Rentals for Winter in Middletown. As only the top 3% of homes go on to become Plum Award winners, you can be certain that your chosen home will be ideal for you. Each home in our range must pass 3 rounds of testing, and comes fully furnished with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Make the most of the chilly season, and wrap up warm in a comfortable Winter Holiday Rental in Middletown. Reach out to our caring team of experts, who love nothing more than helping you discover the perfect home for your trip.
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