Find & compare winery hotels in Highland, NY from $110
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Top Highland Winery Hotels

SureStay Plus Hotel by Best Western Highland Poughkeepsie
Highland winery hotels
Drink in the view at a winery hotel
A trip to wine country is a lovely way to bond with your best friends or invigorate your relationship. Plan a group break or a couples getaway with Travelocity, and enjoy great conversation, stunning scenery, and of course, plenty of wine. If you prefer solo travel, a winery trip is also an excellent way to make new friends or spend some reflective time. Highland winery tours keep the pinot flowing and the schedule going, so all you have to do is enjoy the ride. See the best wineries in Highland and soak up vineyard scenes as you learn about varietals. Pick your favorites and purchase a few bottles to savor at home.
Taste the difference at Highland wineries with lodging
When you stay at Highland wineries, half your travel planning is taken care of. No need to worry about where to eat and drink, where to stay, and what to do. Winding through wine country and stopping to taste the best area offerings, you’ll wonder if there’s any other way to live. After all, what’s better than leisurely, flavor-filled travel?
Highland winery hotels let you take every day at your own pace and enjoy the tastes. On a winery trip, the rules are simple: enjoy yourself. There’s no one to say breakfast wine isn’t a thing or that more than two afternoon naps is too many. This is your time to relax and do what you usually only reserve for Saturdays—drink wine, be with loved ones, meet new people, and have a blast.
Highland hotels essential information
Accommodation | 1,530 hotels |
---|---|
Lowest Price | $110 |
Highest Price | $110 |
Popular hotels | SureStay Plus Hotel by Best Western Highland Poughkeepsie, Atlas Motor Lodge |
Recent Highland hotel reviews by fellow wanderers

Hampton Inn & Suites Poughkeepsie
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