Winchester-Frederick County Convention & Visitors Bureau

Bed & Breakfast / Inns

Herds Inn at Hedgebrook Farm

The Herds Inn is a rustic 2-bedroom log cabin located on a working dairy farm, and constructed from two restored 1800's tobacco barns combined with hand hewn logs. The home has a large kitchen, dining area, two bedrooms, 2 full baths, a large living area with a beautiful limestone fireplace, and a sleeper sofa. The farm is home to donkeys, llamas, horses, peacocks, chickens, ducks, and more. The cabin’s front porch is the perfect spot to watch farm animals grazing in the green pastures and views of the large golden sun sliding down behind the North Mountains as it sets in the west.

690 Shady Elm Road
Winchester, VA 22602
(540) 323-1472

The Inn at Vaucluse Spring innatvaucluse manorhouse web

A romantic 15-room bed and breakfast on 100 scenic acres, just 20 minutes south of Winchester. From the elegance of the historic Vaucluse Manor to the warmth of an 1850’s log house, to the privacy of individual cottages, guests may choose from rooms with Jacuzzis, fireplaces, and some with water or mountain views.  A decadently delicious breakfast is included in the room rate. Evening dining featuring outstanding contemporary American cuisine is available by advance reservation only on Tuesday through Saturday nights.

231 Vaucluse Spring Lane
Stephens City, VA 22655
(540) 869-0200
(800) 869-0525 (Toll Free)

Nancy Shepherd House

Built in the late 1700s, this inn is one of several early federal period inns that once lined the streets of downtown Winchester. Enjoy a unique lodging experience in this truly historic early Virginia tavern, located within walking distance of Old Town’s charming shops and numerous restaurants. The home is filled with authentic early American furniture and real artifacts found during its restoration. A hot breakfast is available on-site, and the innkeeper is a court-appointed civil wedding officiant.

618 S. Loudoun Street
Winchester, VA 22601
(540) 247-5073

Old Waterstreet Inn

Old Waterstreet Inn is a grand old home located in the historic district of Winchester, just 2 blocks from the charming walking mall, where you'll find interesting shops, restaurants, galleries, and nightlife. The federal style brick home, which is designated a Winchester Historic Building, was built in 1840-1890. Architectural details enhance the elegance of the inn, with its high ceilings, classic archways and moldings, fireplaces, lovely staircase, and built-in corner cabinets. On winter evenings, guests can enjoy the glowing fireplace in the living room, and in warm months, guests can relax on the terrace garden, or in the yard with its colorful flowerbeds. Included in your stay is a full hot breakfast served in the gracious dining room.

217 W. Boscawen Street
Winchester, VA 22601
(540) 665-6777

Pembroke Springs Retreat

Situated at the base of the Great North Mountain in the Northwestern part of the Shenandoah Valley, Pembroke Springs is located on a 175 acre tract of field and natural forest; with a stream, a pond and numerous springs. There are five guest bedrooms with private individual bathrooms, a meeting room, a common room and traditional Japanese baths fed by a natural spring. Fish in the stocked pond, play tennis on the acrylic tile tennis court, or take nature walks on miles of on-site hiking trails.

6238 Wardensville Grade
Star Tannery, VA 22654
(540) 877-2600

Wayside Inn

The first travelers to the Inn started coming in 1797, pausing for bed and board as they journeyed across the Shenandoah Valley. Today, the tradition continues as each visitor receives a warm welcome back to a bygone era of fine food and lodging. Each of 22 guest rooms and suites is uniquely decorated with antiques, fine art, object d'art and an interesting potpourri of memorabilia. Amenities include an on-site restaurant and tavern serving traditional and regional cuisine, 6 meeting rooms as well as an events room and terrace area.

7783 Main Street
Middletown, VA 22645
(540) 869-1797