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Wayside Inn

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7783 Main St., Middletown, VA 22645
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Wayside Inn
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24 reviews from our community

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Rating summary
  • Sleep Quality
    5 of 5 stars
  • Location
    4.5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    4.5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
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Annandale, Virginia, United States
Level Contributor
102 reviews
18 hotel reviews
common_n_hotel_reviews_1bd8 52 helpful votes
4 of 5 stars Reviewed 2 days ago NEW

We first visited Wayside Inn about 15 years ago. We decided to return because of such fond memories. This place is definitely worth a visit and makes a perfect location for a weekend get away. Surround the inn are tons of wineries, a farm brewery and lots of hiking. The inn itself is the oldest, continually operating inn in the... More 

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Woodstock, Virginia
Level Contributor
11 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed 2 weeks ago

We stayed here for our 44th Anniversary and it was so relaxing and wonderful. The food was delicious and very generous. They had music in the bar that eveing. Our bedroom was very comfortable and quiet. This historical Inn is outstanding! Right off I-81 in Middletown, VA. Great stay for couples or just to get away. Near attractions as Civil... More 

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Level Contributor
23 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed 3 weeks ago

We were on our way to Washington DC for vacation and thought this would be a great place to stay before heading in to DC. The Owners and Staff were Great!!! The Inn has such Historical Value it is worth visiting. We had two Adjoining rooms #2 and #3. The owners let us have the run of the inn exploring... More 

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Winchester, Virginia
Level Contributor
113 reviews
18 hotel reviews
common_n_hotel_reviews_1bd8 58 helpful votes
2 of 5 stars Reviewed May 19, 2015

This review is of Larrick's Tavern. We decided at the last minute to eat there while nearby. We dined there years ago and our meal was not good at all but new owners could make a difference. We sat at the bar and were the only people at that time on a Saturday afternoon. Our waitress was too busy playing... More 

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Saint Clairsville, Ohio
Level Contributor
6 reviews
4 hotel reviews
5 of 5 stars Reviewed April 16, 2015

What we found was a beautiful historic inn with the most wonderful hosts and staff. Seated in the "slaves kitchen", we enjoyed a first class steak with excellent service. After dinner we had a delightful and informative conversation with George and other guests of the inn. George graciously allowed our ghost hunt and we stayed in room 14, one of... More 

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Chester, Virginia
Level Contributor
6 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed February 22, 2015

My wife and I stayed at the Historic Wayside Inn on Thursday night, February 12, 2015. It was a cold evening but my wife and I were immediately welcomed into the warm Inn, complete with a nice fireplace at checkin. We had a wonderful all you can eat Lasagna dinner buffet, complete with fresh salad and bread. After dinner George... More 

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Middletown, VA
Level Contributor
10 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed January 9, 2015

First time eating back at The Wayside Inn in many years. The new ownes are delightful. The food was great and the atmosphere was quaint and warm. They let us take a tour of the rooms upstairs when we got done eating. I am so glad this is back in operation. We plan to eat there in the near future.... More 

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Falls Church, Virginia
Level Contributor
4 reviews
common_n_hotel_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed December 26, 2014

Had a great stay, comfortable bed, excellent food, outstanding peanut soup and delightful hosts. Couldn't ask for a more enjoyable weekend. Used the Inn as the basis for side trips to Winchester and the country-side.

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Washington DC, District of Columbia
Level Contributor
18 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 8 helpful votes
5 of 5 stars Reviewed December 22, 2014

If you like history, four poster beds, antique furniture, creaky wooden floors, and a friendly staff that treats you like family, this is a place for you. Each room is unique. The halls wander up and down and around. We kept expecting to hear the clip clop of horses outside. For readers there are lots of classic books to pull... More 

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Camden, South Carolina
Level Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed November 12, 2014

Arrived in Middletown in the middle of the night after a long drive from Connecticut. The Wayside Inn jumped out as the place to stay. No corporate script; just great personalized hospitality in a setting that no corporate hotel could ever hope to duplicate. There is nothing like sleeping in a massive early 19th century bed on a modern mattress... More 

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