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Wayside Inn (Room #21) Hite Guest Room

Room 21 ~ The Hite Guest Room has a double bed and a bath with a shower (no tub). This room is up the southern staircase on the 2nd floor. The Hite was named for Major Isaac Hite, Jr, who built Belle Grove in 1797 close to the battle site of the Cedar Creek Battle in Middletown, Virginia. Hite was the brother-in-law of James Madison. Thomas Jefferson helped design Belle Grove. Please note: The Wayside Inn 1797 does not have an elevator. Check-in time begins at 3 pm, check-out time is by 11 am.

Wayside Inn (Room # 19) Massanutten Guest Room

Room 19 ~ The Massanutten Guest Room has a double bed and a full bath with a standard tub. This origin of the name for this room has a couple of versions. One is that it was named by the local Native Americans. "Massa" which means ground and "Nutten" means potato. Another version is that the Native Americans named it the Great Lookout Mountain. This room is one of three rooms on the first floor in the south wing. Check-in time begins at 3 pm, check-out time is at 11 am.

Wayside Inn (Room #7) Jefferson Guest Room

Room 7 ~ The Jefferson Guest Room has a full/double bed with a full bathroom. It is located up the main staircase on the 3rd floor. This room also connects to the Taylor Guest Room # 8. (If you are traveling with family, this set of rooms is a great option!) The room was named after Thomas Jefferson, the 3rd president of the United States. Thomas Jefferson was one of the U.S. presidents born in Virginia. Check-in time begins at 3 pm, and check-out time is at 11am.

Wayside Inn (Room #15) Bernstein Suite

The Bernstein Suite has a Queen bed and a full bathroom. This suite has a separate sitting room and a small separate sunroom. This lovely suite is popular choice for a new bride & groom. It is located up the northern staircase and on the 2nd floor. The Bernstein Suite was named after former owner Leo Bernstein. Mr. Bernstein was a banker, investor, developer and philanthropist. He owned Wayside Inn from 1960 to 2008. Wayside Inn 1797 does not have an elevator.

Wayside Inn (Room #20) Rutherford Stateroom

Room 20 ~ The Rutherford Guest Room has 2 three quarter beds (a bed sized between a twin and a double) and a full bathroom. This room is located up the southern staircase on the 2nd floor. This room was named for a local citizen who was the innkeeper and owner of the Hotel Strasburg, previously owned by Leo Bernstein, former owner of Wayside Inn. Please note: The Wayside Inn 1797 does not have an elevator. Check-in begins at 3 pm, check-out time is at 11 am.

Wayside Inn (Room #1) Jubal Early State Room

Room #1 ~ The Jubal Early State Room has a double bed, full bathroom, and bathtub. Please note: the bathroom is uniquely positioned down a couple of stairs. This beautiful room also features a small sitting area. The room is located on the 2nd floor, up the main staircase. It was named for General Jubal Early, who stayed in this room around the time of the Battle of Cedar Creek. Check-in time begins at 3 pm, and check-out time is at 11 am.

Wayside Inn (Room #24) Monroe Guest Room

The Monroe Guest Room has a /double bed with a full bathroom. This room is located up the southern staircase and is on the 2nd floor. This room is not recommended if you are over 5 foot 6 inches tall because of the unique bed frame. This room was named for James Monroe, the 5th president of the United States. Monroe was one of the U.S. Presidents born in Virginia. Please note: The Wayside Inn 1797 does not have an elevator.

Wayside Inn (Room #22) Byrd Guest Room

Room 22 ~ The Byrd Guest Room has a queen bed and a bathroom with a shower (no tub). This room is located up the southern staircase on the 2nd floor. This room was named for the former governor of Virginia, Harry F. Byrd, Sr. He was from nearby Berryville, VA. Please note: The Wayside Inn 1797 does not have an elevator. Check-in time begins at 3:00pm, check-out time is by 11 am.

Wayside Inn (Room #18 ) Shenandoah Guest

Room 18 - The Shenandoah Guest Room has a queen bed and a bath with a shower only (no tub). The Shenandoah Guest Room is in the South wing on the 1st floor. This guest room was named for the Shenandoah Valley. The history of Wayside Inn is very important to the Shenandoah Valley. Check-in begins at 3 pm, check-out time is at 11 am.

Wayside Inn (Room #17) Lee Guest Room

Room 17 ~ The Lee Guest Room has a full/double bed, a bathroom with a shower (no tub). This room is located in the southern wing on the 1st floor. It was named for General Robert E. Lee, who was from Virginia. Lee visited the Shenandoah Valley throughout his lifetime. Check-in time begins at 3 pm, check-out time is at 11 am.

Wayside Inn (Room #5) Middletown Guest Room

The Middletown Guest Room has a queen bed with a full bathroom. This room is located up the main staircase and is on the 2nd floor. This room was named after the town of Middletown, Virginia where Wayside Inn is located. The town was chartered on May 4, 1796. Wayside Inn 1797 does not have an elevator.

King Suite l George Washington l Fireplace Lounge

Set in the heart of Winchester, this iconic Georgian Revival hotel offers elegant comfort and proximity to dining, wineries, and trails. This spacious suite includes a separate living room and gas fireplace for elevated relaxation. A great choice for extended stays or romantic escapes.