Wayside Inn

Overview
7783 Main St., Middletown, VA 22645 United States
Near Cedar Creek and Belle Grove National Historical Park
Call to book 1-800-219-2797
Group Sales: 1-800-906-2871
AI Insight

The cool thing about Wayside Inn is its charming colonial atmosphere and its convenient location near historical sites and wineries.

Highlights
Free WiFi
Uncovered parking
Pets allowed
Select your room
4.0
06-Feb-2026
"Just us"

This is a Harvest Host for Spring, summer and fall not Winter. We could make use of the electric as it was off. We knew we were staying at the Wayside Inn for two nights to decompress from New York winter weather, but didn't expect such cold temps here. Staff very friendly and helful. Directed us to Shaffers BBQ and Market. Met a local guy who shared his table with us for a nice chat. BBQ very good, portions large. Next, told us about the Daily Buzz, local coffee shop, about two doors down from the Inn. Great breakfast, large selection of cofffes and teas, plus the menu. Also directed us to theItalian Touch were we shared a pizza and salad. Staff friendly, pizza very good. Finally it was Thursday and the kitchen was open at the Inn (weekends only this time of year. Clem's Kitchen breakfast was super good. Eggs, homemade biscuits were devine, but the potatoes very excellent. Boiled, then smashed, deep fried and then put in a fry pan with evoo, rosemary and garlic. Asfar as the Inn itself, we had it to ourselves the first night. A lot of history here, including that the war between the states shared this Inn! Whoever "won" that day got the Inn. Crazy. Lots of common rooms, lots of bedrooms, lots of antiques, lots to read about and explore here. The second night another couple stayed, but we didn't see them until the next morning and they left without having that grea breakfast. Their mistake. I would stay here again.

(Individual traveler, booked 1 room)
Verified Review, stayed from Tue Feb 03 to Thu Feb 05 2026 at a $84.99 average nightly rate.
5.0
12-Sep-2025
"Charming Inn"

Nice place to stay. Luca at the front desk was so friendly and helpful. Location was perfect!

(Individual traveler, booked 1 room)
Verified Review, stayed from Wed Sep 10 to Thu Sep 11 2025 at a C$179.22 average nightly rate.
4.0
02-Jul-2025
"Brittney was very nice and accommodating."

Would stay there again.

(Individual traveler, booked 1 room)
Verified Review, stayed from Sat Jun 28 to Sun Jun 29 2025 at a $110.99 average nightly rate.
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Check-In 3:00 PM - 9:00 PM

Check-Out 11:00 AM

Check-In Instructions:

  • Extra-person charges may apply and vary depending on property policy
  • Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
  • Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
  • This property accepts credit cards, debit cards, and cash
  • Safety features at this property include a fire extinguisher, a security system, and a first aid kit
  • Ballroom
  • Banquet hall
  • Books
  • Check In: 3:00 PM - 9:00 PM
  • Check Out: 11:00 AM
  • Coffee/tea in common areas
  • Concerts/live shows
  • Couples/private dining
  • Designated smoking areas
  • Evening entertainment
  • Express check-out
  • Fireplace in lobby
  • Free RV, bus, truck parking
  • Free WiFi
  • Free long-term parking
  • Free self parking
  • Front desk (limited hours)
  • Front entrance ramp
  • Garden
  • Handrails in stairways
  • Housekeeping on request
  • Library
  • No cribs (infant beds) available
  • No elevators
  • Number of meeting rooms - 1
  • Number of restaurants - 1
  • Off-street parking
  • Only dogs and cats are allowed
  • Outdoor entertainment area
  • Outdoor furniture
  • Parking (limited spaces)
  • Pets allowed
  • Picnic area
  • Private picnics
  • Professional property host/manager
  • Proposal/romance packages available
  • Reception hall
  • Service animals are allowed
  • Service animals are exempt from fees/restrictions
  • Stair-free path to entrance
  • Stairwell handrail height (centimeters) - 84
  • Stairwell handrail height (inches) - 33
  • Terrace
  • Uncovered parking
  • Upper floors accessible by stairs only
  • Wedding services
  • Well-lit path to entrance
  • Wheelchair accessible – no

Essential workers only - NO

Day 1

Breakfast The Apple House - A local favorite for breakfast and brunch. Enjoy homemade pastries and fresh apple cider. Located 3.5 miles from Wayside Inn.
Lunch Thai Winchester - Authentic Thai cuisine with a variety of options. Located 1.8 miles from Wayside Inn.
Dinner The Red Fox Inn & Tavern - A historic inn serving traditional American cuisine. Located 0.2 miles from Wayside Inn.
Activity Belle Grove Plantation - Explore this historic plantation and learn about its rich history. Located 4.7 miles from Wayside Inn.

Day 2

Breakfast The Daily Grind - A cozy coffee shop serving delicious breakfast sandwiches and freshly brewed coffee. Located 0.5 miles from Wayside Inn.
Lunch Violino Ristorante Italiano - Enjoy authentic Italian dishes in a charming atmosphere. Located 1.2 miles from Wayside Inn.
Dinner The Union Jack Pub & Restaurant - A British-style pub offering a wide selection of beers and classic pub fare. Located 0.3 miles from Wayside Inn.
Activity Cedar Creek and Belle Grove National Historical Park - Visit the site of the historic Civil War battle and explore the museum. Located 5.2 miles from Wayside Inn.

Day 3

Breakfast The Wayside Inn Restaurant - Start your day with a hearty breakfast at the inn's own restaurant. Located on-site.
Lunch The Italian Touch - A family-owned Italian deli offering delicious sandwiches and homemade pasta. Located 0.7 miles from Wayside Inn.
Dinner The Wine and Duck Restaurant - A fine dining establishment known for its exquisite wine selection and gourmet dishes. Located 0.4 miles from Wayside Inn.
Activity Skyline Drive - Drive along this scenic road and enjoy breathtaking views of the Shenandoah Valley. Located 8.3 miles from Wayside Inn.

FAQs about Wayside Inn

What time is check in?

Check in time is 3:00 PM - 9:00 PM based on the hotel's local time. Early check in may be available if requested at the front desk on the day of check-in.

What time is check out?

Check out time is 11:00 AM based on the hotel's local time. Late check out may be available if requested at the front desk during your stay.

Is Wayside Inn pet friendly?

Yes, pets are allowed. Only dogs and cats are allowed

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