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Top Chesapeake Bay Winery Hotels

Kilmarnock Inn $165
Kilmarnock Inn

Kilmarnock Inn

34 East Church Street, P.O.Box 1479, Kilmarnock, VA
     
    5.0
    of 5, from 1 reviews
    3.5 out of 5.0 Stars

    A restaurant, free self parking, and a garden are among this bed & breakfast's amenities. Guests will appreciate free perks like daily breakfast and WiFi in public areas. A library, a computer station, and wedding services are also on offer.

    Wedmore Place $144
    Wedmore Place

    Wedmore Place

    5810 Wessex Hundred, Williamsburg, VA
       
      4.8
      of 5, from 5 reviews
      3.5 out of 5.0 Stars

      An attached winery and a fitness center are featured at this boutique hotel. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking.

      Greensprings Vacation Resort by Diamond Resorts $78
      Greensprings Vacation Resort by Diamond Resorts

      Greensprings Vacation Resort by Diamond Resorts

      3500 Ludwell Pkwy, Williamsburg, VA
         
        4.4
        of 5, from 57 reviews
        3.0 out of 5.0 Stars

        This resort features an outdoor pool and an indoor pool. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Enjoy the outdoor tennis court and perks like free self parking and free WiFi.

        Kingsmill Resort $179
        Kingsmill Resort

        Kingsmill Resort

        1010 Kingsmill Rd, Williamsburg, VA
           
          4.2
          of 5, from 25 reviews
          4.0 out of 5.0 Stars

          This smoke-free resort features a golf course, a full-service spa, and a marina. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 2 outdoor pools and perks like free self parking and a free beach shuttle.

          The Historic Powhatan Resort by Diamond Resorts $58
          The Historic Powhatan Resort by Diamond Resorts

          The Historic Powhatan Resort by Diamond Resorts

          3601 Ironbound Rd, Williamsburg, VA
             
            3.8
            of 5, from 105 reviews
            3.5 out of 5.0 Stars

            This smoke-free resort features 2 outdoor tennis courts, an outdoor pool, and a restaurant. Bring the family and enjoy the free kid's club, mini golf, and playground. Enjoy the indoor pool and perks like free self parking and free WiFi.

            Best Western Kilmarnock Hotel $100
            Best Western Kilmarnock Hotel

            Best Western Kilmarnock Hotel

            599 N Main St, Kilmarnock, VA
               
              3.4
              of 5, from 5 reviews
              2.5 out of 5.0 Stars

              This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

              The Holidays in Irvington - A Page out of Norman Rockwell! And Great Shopping! Get Rates
              The Holidays in Irvington - A Page out of Norman Rockwell! And Great Shopping!

              The Holidays in Irvington - A Page out of Norman Rockwell! And Great Shopping!

              Irvington, VA
                 
                0.0 out of 5.0 Stars

                An outdoor tennis court is featured at this cottage, along with a garden.

                Exquisite Waterfront Beach House $99
                Exquisite Waterfront Beach House

                Exquisite Waterfront Beach House

                Scotland, MD
                   
                  0.0 out of 5.0 Stars

                  A garden is available at this cottage.

                  Here is Your Summer Beach Cottage With all Anemities, Eastern Shore, Virginia Get Rates
                  Here is Your Summer Beach Cottage With all Anemities, Eastern Shore, Virginia

                  Here is Your Summer Beach Cottage With all Anemities, Eastern Shore, Virginia

                  Cape Charles, VA
                     
                    0.0 out of 5.0 Stars

                    A garden is available at this cottage.

                    Bay Chalet Get Rates
                    Bay Chalet

                    Bay Chalet

                    71 Holly Creek Dr., Heathsville, VA
                       
                      0.0 out of 5.0 Stars

                      This vacation home features barbecue grills.

                      The Tides Inn $176
                      The Tides Inn

                      The Tides Inn

                      480 King Carter Dr, Irvington, VA
                         
                        4.0 out of 5.0 Stars

                        This smoke-free hotel features a private beach, a golf course, and 4 restaurants. Families will appreciate the children's club, kid-friendly dining, and supervised childcare. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like valet parking and an area shuttle.

                        The Whispering Pines Motel-whitestone Get Rates
                        The Whispering Pines Motel-whitestone

                        The Whispering Pines Motel-whitestone

                        226 Methodist Church Rd, White Stone, VA
                           
                          2.5 out of 5.0 Stars

                          This motel features a seasonal outdoor pool and a spa tub. Guests will appreciate free perks like free self parking and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.

                          Travelers Like You Recently Booked These Chesapeake Bay Hotels

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                          Chesapeake Bay 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. Chesapeake Bay 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 Chesapeake Bay 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 Chesapeake Bay wineries with lodging
                          When you stay at Chesapeake Bay 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?

                          Chesapeake Bay 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.

                          Recent Chesapeake Bay Hotel Reviews By Fellow Wanderers

                          *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.