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The Carriage Inn B&B
3.5 out of 5
417 E Washington Street, Charles Town, WV
The price is $130 per night from Apr 21 to Apr 22

Situated in the historical district, this bed & breakfast is within 1 mi (2 km) of Zion Episcopal Church Cemetery and Hollywood Casino at Charles Town Races. ...

4.9/5Exceptional! (157 reviews)

"This BB was so beautifully decorated and clean. It had a lot of charm and the owners were extremely friendly. I came in town to visit my college roommate who stayed with me and we had a wonderful experience. I would recommend this BB in a heartbeat."…"

Reviewed on Apr 2, 2021

The Carriage Inn B&B
Hillbrook Inn
4 out of 5
4490 Summit Point Road, Charles Town, WV
The price is $161 per night from Apr 19 to Apr 20

Situated near the airport, this romantic bed & breakfast is 2.8 mi (4.5 km) from Summit Point Raceway and 2.8 mi (4.5 km) from Winchester Visitors Center. Hollywood ...

4.8/5Exceptional! (73 reviews)

"Would be perfect in warmer weather. The areal star was the cuisine. Beautiful presentation fine service along with excellent food. Well worth another visit."…"

Reviewed on Mar 6, 2021

Hillbrook Inn
The Ashby Inn & Restaurant
3.5 out of 5
692 Federal St, Paris, VA
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Situated in the historical district, this bed & breakfast is within a 15-minute walk of Paris Barns and Sky Meadows State Park. Burwell-Morgan Mill and Duvall ...

4.7/5Exceptional! (41 reviews)

"Greater at the door as we were exiting our car. Taken on a brief tour of the facilities as we were shown our room. Great way to start our stay. Breakfast the next.morning was delicious. Our server paid just the right amount of attention as I waited for that first cup.of coffee to kick in. Just a ..."…"

Reviewed on Jun 28, 2019

The Ashby Inn & Restaurant
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L Auberge Provencale Bed and Breakfast
3.5 out of 5
13630 Lord Fairfax Highway, White Post, VA
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Situated in White Post, this bed & breakfast is 3 mi (4.8 km) from Dinosaur Land and within 6 mi (10 km) of State Arboretum of Virginia and Burwell-Morgan Mill. ...

4.7/5Exceptional! (16 reviews)
awesome stay!

"My husband and I celebrated our anniversary here and it was amazing. The staff was great from beginning to end. We enjoyed all the delicious food fro dinner and breakfast. We have decided to make this one of our spots when we need to get away from the kids, city and the everyday hustle."…"

Reviewed on Jul 18, 2016

L Auberge Provencale Bed and Breakfast
Smithfield Farm B&B
3 out of 5
568 Smithfield Lane, Berryville, VA
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Situated in Berryville, this bed & breakfast is within 6 mi (10 km) of Holy Cross Abbey, Veramar Vineyard, and The Fire House Gallery. Barns of Rose Hill and ...

5/5Exceptional! (26 reviews)

"Excellent bed and breakfast! We highly recommend and plan to return. Betsy, the Inn keeper, thought of everything. With our late arrival, she had hot tea, cookies, candy and snacks waiting for us. The Smithfield property is an organic farm so breakfast consisted of fresh eggs, honey, and ham from ..."…"

Reviewed on Nov 12, 2019

Smithfield Farm B&B
Holliday House Strasburg
3.5 out of 5
112 East King Street, Strasburg, VA
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Situated in Strasburg, this bed & breakfast is steps from Strasburg Theater and Strasburg Town Hall. Strasburg Museum and Hupp's Hill Civil War Park are also ...

4.7/5Exceptional! (19 reviews)

"The property is very pretty and well-kept, conveniently located on the historic main street, the neighborhood is very charming."…"

Reviewed on Jan 2, 2019

Holliday House Strasburg
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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.

Other property types in Old Town Winchester

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St, Winchester, VA
The price is $98 per night from May 2 to May 3
4.6/5Exceptional! (982 reviews)

"The renovation of the Hotel was excellent and much of the original hotel was still present."…"

Reviewed on Apr 10, 2021

The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is $94 per night from Apr 21 to Apr 22
4.3/5Excellent! (980 reviews)

"It was ok, they keep up with covid-19 procedures."…"

Reviewed on Apr 12, 2021

La Quinta Inn & Suites by Wyndham Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court, Winchester, VA
The price is $94 per night from Apr 20 to Apr 21
4.5/5Wonderful! (203 reviews)

"Everything was A plus however our key never worked because of computer glitch brought by electrical outage. It did not work the entire stay from evening til 11am. No one ever tried to fix it. Otherwise the stay was great"…"

Reviewed on Mar 31, 2021

TRU By Hilton Winchester
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.

Why Stay at a B&B in Old Town Winchester?

Are you on the hunt for a place to stay with a hearty breakfast and a comfortable setting? If you're hoping to find a B&B for your stay in Old Town Winchester but can't find one right in town, there are other options in the surrounding area that may also have what you're looking for. When you want to explore the surroundings in Old Town Winchester, Old Court House Civil War Museum and Shenandoah Valley Discovery Museum are a couple notable museums worth checking out.

B&Bs Near Old Town Winchester

Every B&B has its own unique feel— whether it's a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts the perfect escape. Below are some well-liked B&Bs in the area:

Holliday House Strasburg: 3.5 stars, 3 rooms

  • 17.1 mi (27.5 km) from the heart of Old Town Winchester
  • Cooked-to-order breakfast
  • In-room fireplace

The Carriage Inn B&B: 3.5 stars, 7 rooms

  • 18.2 mi (29.2 km) from the downtown core
  • Library
  • In-room fireplace

Hillbrook Inn: 3 stars, 9 rooms

  • Situated 13.4 mi (21.6 km) from the city center
  • Full breakfast
  • In-room jetted tubs

The Ashby Inn & Restaurant: 3.5 stars, 10 rooms

  • 16.9 mi (27.1 km) from the heart of downtown
  • Full breakfast
  • Restaurant on site

Smithfield Farm Bed and Breakfast: 3 stars, 5 rooms

  • Located 14.2 mi (22.9 km) from the city's core
  • Full breakfast
  • Individually decorated rooms

How to Pack for the Weather in Old Town Winchester

If you're trying to figure out the optimal time to vacation in Old Town Winchester, we've collected some useful weather info to help you plan your getaway:

  • The hottest months are typically July and June, while January and February are the coldest months
  • Average rainfall is 38.39 inches in a year
  • January-March: Daytime temperatures average 58° F and nighttime temperatures average 23° F
  • April-June: 85° F is the daytime average and 37° F is the nighttime average
  • July-September: Daytime averages are around 86° F and nighttime averages are around 49° F
  • October-December: The average temperatures are 71° F during the day and 24° F at night

Sightseeing In and Around Old Town Winchester

Travelers enjoy Old Town Winchester for its array of dining options and interesting historical sites. When you want to explore some cultural attractions on your trip, Bright Box Theater and Old Court House Civil War Museum are worthy sites to check out. You might put Shenandoah Valley Discovery Museum and George Washington's Office on your list if you want to see more of the area.

Travelers also enjoy Old Town Winchester for its:

  • Shopping
  • Cafés
  • Bars
  • Live music
  • Tours

Transportation Options In and Around Old Town Winchester

Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the heart of the city. You can also search for flights into Washington, DC (IAD-Washington Dulles Intl.), which is 41.6 mi (67 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

Frequently asked questions

Searching for B&Bs in Old Town Winchester?
If you want to find an accommodation with fewer rooms than the traditional hotel and a more personalized environment, a bed and breakfast may be the perfect thing for your trip to Old Town Winchester. When you want to venture out to explore Old Town Winchester, consider browsing the exhibits at Old Court House Civil War Museum.
Are you thinking about B&Bs over traditional hotel rooms?
Every B&B has a unique charm— whether it’s a picturesque garden or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts a fun place to get away.
What are the top B&Bs in Old Town Winchester?
Below are some well-liked B&Bs in the area: The Carriage Inn B&B: 3.5 stars, 7 rooms. 18.2 mi (29.3 km) from the heart of Old Town Winchester. Enjoy the unique décor and in-room fireplace. Hillbrook Inn: 4 stars, 9 rooms. 13.5 mi (21.7 km) from the downtown core. Enjoy the free full breakfast and bar/lounge. L Auberge Provencale Bed and Breakfast: 3.5 stars, 14 rooms. Situated 8.8 mi (14.1 km) from the heart of Old Town Winchester. Enjoy the free full breakfast and onsite dining. The Ashby Inn & Restaurant: 3.5 stars, 10 rooms. 16.9 mi (27.2 km) from the heart of downtown. Enjoy the free full breakfast and onsite dining. Smithfield Farm B&B: 3 stars, 3 rooms. Located 14.3 mi (23 km) from the core of Old Town Winchester. Enjoy the arcade game room and library.
What's the best time of year to stay at a B&B in Old Town Winchester?
When you’re planning your trip to Old Town Winchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and June with an average temp of 71°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Old Town Winchester is 38 inches.
What is there to do in Old Town Winchester?
Travelers enjoy Old Town Winchester for its array of dining options and interesting historical sites. When you want to explore some cultural attractions on your trip, Bright Box Theater and Old Court House Civil War Museum are worthy sites to check out. You might put Shenandoah Valley Discovery Museum and George Washington’s Office on your list if you want to see more of the area.
How can I get to and around Old Town Winchester?
Planning your excursions in and around Old Town Winchester is easier with these transportation options. Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) away from the city center. If you’d like to venture out around the area, you may want to rent a car for your trip.

More trip options