Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Tonight Apr 3 - Apr 4
This weekend Apr 3 - Apr 5
Next weekend Apr 10 - Apr 12

Top Middletown Winery Hotels

Get Rates
Wayside Inn

Wayside Inn

3.5 out of 5.0 7783 Main St, Middletown, VA
4.5/5
(4 Reviews)
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
$63
Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2.0 out of 5.0 91 Reliance Road, Middletown, VA
2/5
(1 Reviews)
This hotel features an indoor pool and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Map

Recent Middletown Hotel Reviews By Fellow Wanderers

Middletown 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. Middletown 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 Middletown 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 Middletown wineries with lodging
When you stay at Middletown 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?

Middletown 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.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.