Title: Book the Best Hotels with BARS in Old Town Winchester in 2025 | Expedia.ca [Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Old Town Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide)[Old Town Winchester Vacations](https://expedia.ca/Old-Town-Winchester.d6164092.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Bar in Old Town Winchester, VA from CA $101 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Old Town Winchester Hotels with Bar ## Top Old Town Winchester Hotels with Bar ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/bff9ad76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George Washington Hotel, A Wyndham Grand Hotel Old Town Winchester 9.4/10 Exceptional (1008) "Very nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $177 CA $201 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Down comforters, Select Comfort beds, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/cab9baeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/5ea79918.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Winchester Winchester 8.8/10 Excellent (893) "Very friendly staff and clean facilities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patty CA $150 CA $163 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/ad5604d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9cf3d079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/b96d495c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows Front Royal 9.0/10 Wonderful (1002) "Great stay, great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bhargav CA $148 CA $168 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Elevator](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/9fcf0199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/9ef74ac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/e47a228e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Strasburg/Shenandoah Valley Strasburg 8.2/10 Very good (1004) "Our stay was fine, convenient location to our planned activities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mitchell CA $101 CA $113 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/7ff8d7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/b6f40366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/ee4df7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Winchester Se-Historic Gateway by IHG Winchester 9.0/10 Wonderful (1003) "Very clean & comfortable. Staff was very helpful & pleasant." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert E CA $104 CA $117 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/689131eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a7fe3c2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/037b096c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily breakfast for a fee](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a36008d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Winchester Winchester 8.8/10 Excellent (500) "I have stayed here a few times and always enjoyed the stays." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $134 CA $152 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Winchester-Hotels-Hilton-Garden-Inn-Winchester.h2169428.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/eaa4b7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/9aa4d92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/46449a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (The Bamford Suite)](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/50b1e67b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillbrook Inn Charles Town 8.6/10 Excellent (670) "We had an amazing day at the Hillbrook Inn. I recommend this to anybody who would like a quiet serene stay. Staff is wonderful and the food is amazing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karley CA $233 CA $297 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/8c81eb2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Renoir](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/ff749f7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/a0a5a84e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Matisse at The Villa](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/957a1979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L'Auberge Provencale Inn & Restaurant Boyce 9.6/10 Exceptional (172) "Wonderful staff and service!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eliel Constantine CA $381 CA $421 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Winchester-Hotels-LAuberge-Provencale.h15945622.Hotel-Information) ![2 bars/lounges, sports bar](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/b6dd3662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/64e72433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/56958e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/14125876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn & Suites - Charles Town, WV Charles Town 8.6/10 Excellent (1029) "Great for the value!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tabitha CA $89 CA $101 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/fd85fd97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a19abecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a984ecc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/29d89638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Charles Town - Hollywood Casino Charles Town 8.6/10 Excellent (504) "Great place to stay to go to the casino" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $168 CA $202 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18®ionId=6164092&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Old Town Winchester Hotel Reviews ![Hampton Inn Winchester-University/Mall Area](//images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 10/10 Excellent "good breakfast and service. room felt a bit cramped and tv did not work " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Travelodge by Wyndham Winchester](//images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Clean. Comfortable. Nice staff. Breakfast was good. " [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "XXXX" [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Ramada by Wyndham Strasburg/Shenandoah Valley](//images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 10/10 Excellent "Great!" [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Rodeway Inn & Suites - Charles Town, WV](//images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/b6dd3662_y.jpg) ### Rodeway Inn & Suites - Charles Town, WV 10/10 Excellent "The carpet was old and stained up. Low dingy, but the room overall was clean. Bathroom was clean." [](https://expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "Service was great!!" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "We had a pleasant stay, staff was really nice and the room was spotless. Easy check in, the breakfast in the morning was enjoyable. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 10/10 Excellent "Staff were great. Beautiful property. Registration process was hampered by slow computers. Breakfast service was really slow at Houlihans " [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Hampton Inn Front Royal](//images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "The staff was amazing! As we zipped in and out we were always welcomed or wished a good day. Big smiles and just super nice! Loved the coffee/tea area. Talk about coming home. My one comment would be that the trash cans were never emptied in our room or bathroom. And because the cans are so small by end of day two they were overflowing. When the gal came to do our room we were just getting ready to leave and she said she couldn’t come in while guests were in the room. (Think that is a good safety concept for both her and guests.). So we told her we were leaving almost immediately and could she please empty our trash. Never came in as trash remained over flowing. When checking out Monday morning I mentioned this and the woman at the desk said “next time just put the trash outside your room in the hallway.” My comment is “When paying as much as was for stay of three nights - your trash cans should definitely be emptied!” All in all can not say enough about the quality and helpfulness of all the rest of the staff. Excellent group! " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Old Town Winchester? > Though you might not find a hotel in Old Town Winchester well-known for its bar, you will find 12 properties to choose from, some of which will have an onsite bar where you can unwind with an evening cocktail after sightseeing. While you're here, consider a visit to Bright Box Theater and Shenandoah Valley Discovery Museum. ### What are the best hotels with bars in Old Town Winchester? > Here are some favorite hotels with bars in and around Old Town Winchester: [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information): Hotel with 2 restaurants. Enjoy the bar, free WiFi, and full-service spa. [Red Roof Inn Winchester, VA](https://www.expedia.ca/Winchester-Hotels-Red-Roof-Inn-Winchester.h24072.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [La Quinta Inn & Suites by Wyndham Winchester](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [Comfort Inn & Suites Winchester](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information): Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. [Hampton Inn Winchester-University/Mall Area](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information): Enjoy the 2 bars, free breakfast, and free WiFi. ### What is there to do in Old Town Winchester? > To experience the area's highlights, consider visiting Bright Box Theater, Shenandoah Valley Discovery Museum, and Winchester Little Theater, and then find a cozy spot for a nightcap. Other places to see include Handley Regional Library and Old Court House Civil War Museum. Old Town Winchester is popular for its top-notch restaurants. ### How can I get to Old Town Winchester and around the area? > You might want to make the most of these transportation choices in and around Old Town Winchester: Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) away. You can also search for flights into Washington Dulles Intl. 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