Find & compare winery hotels in Chester, VA

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

Chester 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.

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Recent Chester hotel reviews by fellow wanderers

The Jefferson Hotel

The Jefferson Hotel

2 out of 5
Posted 1 day ago
Travelocity Verified Review
"1) Dodgy area. not sure I would walk the area at night. View from my room looked out on a graffiti covered building across a parking lot. Be prepared for ambulances and sirens blasting at least 2 or 3 times during the night. 2) rooms are all different, but my room was...less than optimal. The bed was was 9 feet from the door which opened directly into the main part of the room When I lay on my side, bright lights from the hallway shone through the cracks between the door and the frame. It was like staring at bright night light. It's always better when the door does not open directly into the main room, which shields the occupant from light and noise. 3) I did not care for the mattress. I am not a fan of memory foam, even it is only a topper. It's very hot to sleep on. Between the light from the door and the uncomfortable mattress, I did not have a good night's rest. 4) The hotel shuttle does not run often enough. We attended an event at the train station, and when we called the hotel for a pickup, they said they could not be there for an hour. We called an uber instead; I think the room was over-priced. I've stayed in nicer hotels for less. The lobby is impressive, but one doesn't sleep in the lobby. I probably would have given the experience 3 stars instead of 2 if the price were more reasonable. "
A verified traveler stayed at The Jefferson Hotel
The Jefferson Hotel

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