We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Book On TripAdvisor Bonus Book your hotel on TripAdvisor — then save 20% on things to do for your trip. Use code BOOKTOSAVE.

Wayside Inn

Certificate of Excellence
7783 Main St., Middletown, VA 22645
Hotel amenities
Book on TripAdvisor
Trusted partner. We work with Tingo to make your booking as easy as possible.
Secure payments. We use industry-leading practices to keep your information secure.
Enter dates for best prices
powered by PriceFinder
1 room
Check In Check Out
Please enter your travel dates to continue
Check Availability
Book on
or compare prices from up to 200 sites including:
Management photos
Wayside Inn
View Map
{"widget":{"name":"ibex_photo_carousel","template":"ibex_photo_carousel__widget","dust":{"nav_controls":"ibex_photo_carousel__nav_controls"},"divClasses":"prw_rup prw_ibex_photo_carousel","moduleList":["handlers","shims"],"js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))","shims":"(ta.prwidgets.getjs(this,'shims'))"}},"containerClass":null}
Add Photo Write a Review

47 Reviews from our TripAdvisor Community

Traveler rating
Traveler type
Time of year
Language
Showing 47: English reviews
Los Angeles, California
Level Contributor
5 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 3 helpful votes
4 of 5 stars Reviewed 2 days ago NEW

My travel pal and I needed a short-notice, affordable room on our cross-country road trip, and had little idea what a gem we'd booked until we arrived. What a treat to discover the oldest continuously operating inn in the country, packed with antiques, art, curiosities, and stories, in all its crooked-angle glory. No extra charge for ghosts (we were assured... More 

Helpful?
Thank MischSafariste
Colorado
Level Contributor
39 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 16 helpful votes
5 of 5 stars Reviewed 1 week ago

This place is amazing! Due to the circumstances of my work, I was not able to stay here (it was not on the list of places I could book) but I was able to have an absolutely lovely meal on 6/7/2016. The proprietors were quite gracious and the food was wonderful. I've told my husband we need to stay here... More 

Helpful?
Thank a_searcher
Rockville, Maryland
Level Contributor
8 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed 4 weeks ago

We stayed here for our son & daughter in law"s wedding. We were so delighted by the beauty, history and friendliness of the owners and staff. We had a great room, comfortable and simply beautiful. They have a restaurant and the food and service exceeded our expectations. We only stayed for the weekend, but could not have had a more... More 

Helpful?
1 Thank Jan S
Emporia, Virginia
1 review
5 of 5 stars Reviewed 4 weeks ago

This inn is fascinating due to its age, & its lovely period decor. Our stay was very comfortable, and the innkeepers made us feel right at home. The breakfast included in the price is hearty & delicious. It is easy to find & conveniently located for visiting the many attractions in the area

Helpful?
Thank LXL91
San Francisco, California
Level Contributor
10 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed 4 weeks ago

This historic inn fascinated me with its rooms and wings sprouted like a weed. It's filled with antiques and lots of old wood paneling. It has multiple common rooms and a very spacious dining room and tavern (not open when we were there). We were there mid week when the inn was pretty empty so I was able to see... More 

Helpful?
Thank playajewel
Stafford, Virginia
Level Contributor
10 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed June 18, 2016 via mobile

My wife and I were looking for a place to stay in northwestern Virginia while we checked out wineries and explored Winchester. Bottom line is that we really enjoyed our stay at the Wayside Inn. Located about 10 miles from Winchester, this is one of the oldest continually active inns in the country. Everywhere you turn, there is history, from... More 

Helpful?
Thank Robert C
USA
Level Contributor
42 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 18 helpful votes
5 of 5 stars Reviewed June 12, 2016

We love traveling with our dog, a 35 pound female Border Collie, but not every place understands that she is a better tenant than most humans. Fortunately the innkeepers at Wayside know how to pamper pooches as well as their guests. We received a "treat" from innkeeper Becky Reeves upon checking in and the kind of treatment that you'd expect... More 

Helpful?
Thank Oleguy
1 review
5 of 5 stars Reviewed June 1, 2016 via mobile

We were on the hunt for breakfast after find the Old Mill Grill closed and not wanting fast food fare. While the restaurant was not technically open for people not staying at the inn, we were invited in to eat so we 'wouldn't go hungry'. Next time we are in the area will make a point of actually staying here.

Helpful?
Thank kppaaz
1 review
common_n_hotel_reviews_1bd8 1 helpful vote
4 of 5 stars Reviewed April 24, 2016 via mobile

we stayed two nights there for a weekend. It wasn't super clean, however it worthed every second of it. We only wanted a place to crash for our nights but we ended up spending our mornings there since it was really beautiful. The staff were friendly and the all you can eat breakfast was amazing and cooked specially for our... More 

Helpful?
1 Thank Mehdi K
Belchertown, Massachusetts
Level Contributor
27 reviews
common_n_hotel_reviews_1bd8 11 helpful votes
4 of 5 stars Reviewed April 18, 2016 via mobile

I made this reservation while planning our return from Chattanooga via the Skyline Drive in the Shenandoah National park. As the beginning of our last leg to home was going to be starting in Virginia it made sense to seek accommodation close to the beginning of Rte 81 . after we exited the 105 mile long trip on the Skyline... More 

Helpful?
Thank MrQ129
Questions? Get answers from hotel staff and past guests. Ask a question

84 photos of this hotel

Traveler photos: See what travelers like you saw

Viewed
All Traveler Photos (73)
Viewed
Hotel & Grounds (36)
Viewed
Dining (6)
Viewed
Family/Play Areas (1)
Viewed
Room/Suite (11)
Viewed
Bathroom (1)
Viewed
Other (18)

Management photos: Courtesy of the property manager

Viewed
All Management Photos (11)
Viewed
Hotel & Grounds (2)
Viewed
Dining (8)
Viewed
Other (1)
Check In Check Out
Hotels you might also like...
Also consider these accommodations in or near Middletown
6.6 mi away
Hampton Inn Front Royal
Hampton Inn Front Royal
#1 of 9 in Front Royal
4.5 of 5 stars 665 reviews
7.7 mi away
Country Inn & Suites By Carlson, Winchester
5.4 mi away
Hotel Strasburg
Hotel Strasburg
#2 of 5 in Strasburg
4.0 of 5 stars 192 reviews
Show Prices
Show Prices
Show Prices
3.9 mi away
Fairfield Inn & Suites Strasburg Shenandoah Valley
5.9 mi away
Holiday Inn & Suites Front Royal Blue Ridge Shadows
0.4 mi away
Econo Lodge Inn & Suites
Econo Lodge Inn & Suites
#2 of 3 in Middletown
3.0 of 5 stars 11 reviews
Show Prices
Show Prices
Show Prices
Questions? Get answers from hotel staff and past guests. Ask a question

Amenities

Highlights
  • Free Parking
  • Room Service
  • Restaurant
  • Bar/Lounge
  • Free Breakfast
About the property
  • Wheelchair access
Food & drink at the hotel
Wayside Inn
Wayside Inn
Cuisines: American, Bar, Grill, Pub
Things to do
  • Restaurant
  • Bar/Lounge
Room types
  • Non-Smoking Rooms
  • Family Rooms
  • Accessible rooms
In your room
  • Air Conditioning
Internet
  • Public Wifi
Services
  • Free Parking
  • Room Service
  • Free Breakfast
Official Description (provided by the hotel)
Historic inn that has earned the distinction of being "America's First Motor Inn." ... more   less 

Additional Information about Wayside Inn

Address: 7783 Main St., Middletown, VA 22645
Location: United States > Virginia > Middletown
Price Range: $100 - $127 (Based on Average Rates for a Standard Room)
Hotel Class:3.5 star — Wayside Inn 3.5*
Number of rooms: 24
Reservation Options:
TripAdvisor is proud to partner with Orbitz, Hotels.com, Expedia, Travelocity and Hotwire so you can book your Wayside Inn reservations with confidence. We help millions of travelers each month to find the perfect hotel for both vacation and business trips, always with the best discounts and special offers.
Also Known As:
Wayside Hotel Middletown
Is This Your TripAdvisor Listing?
Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.
Claim Your Listing
Enter dates for best prices
Check In Check Out
Price Your Stay