Wayside Inn Middletown

Middletown, United States View on map
Editor's Pick

"Larrick's Tavern serves French Dip with homemade chips. Antique furniture fills the historical common areas. Best for road-trippers, less so for anyone requiring on-site staffing after dark."

From US$ 170 US$ 146 per night
Save 14%
Check-in
24 Sept 2026
Check-out
25 Sept 2026
Guests
2 guests

Adults:

2

Children:

0
  • Free cancellation
    on many rooms
  • No booking fees
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Why guests choose Wayside Inn

  • Historic Inn
    Oldest continuously operating
  • Larrick's Tavern
    Live music & local ingredients
  • Handcrafted Cocktails
    Historic tavern bar
  • Pet-Friendly
    Dogs welcome
  • Shenandoah Access
    2 miles to Skyline Drive
  • Local Breakfast
    Homemade jam from garden

Overview

The 3-star Wayside Inn Middletown offers easy access to the performing arts theater "Wayside Theatre", which is situated approximately 5 minutes' walk away. High-speed Internet access is offered in public areas and a car park is available on site.

Stonewall Jackson Museum is located 3 miles from the hotel, and Cedar Creek Battlefield Foundation is 1.3 miles away. Hupp's Hill Civil War Park Museum is also located about 15 minutes' drive from the Wayside Inn. Guests might as well enjoy proximity to Cedar Creek and Belle Grove National Historical Park, situated 0.4 miles away. The nearby cultural attractions include Belle Grove Plantation, which is 25 minutes' walk from this Middletown hotel.

Guests can unwind at the on-site lounge bar with a favorite drink. You can dine at Wayside Inn, 500 feet away.

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  • Hotel class
    3 stars
Wayside Inn
Our tips

Should you book Wayside Inn?

Perfect if you
  • Want a free breakfast with locally sourced ingredients, including homemade jam from the innkeeper's garden.
  • Are traveling with a pet - the inn accommodates pets, a flexibility not all historic properties offer.
Maybe skip if you
  • Need level floors and standard door angles - the old architecture includes sloped floors and doors cut at angles.
Best for
  • Staying in the oldest continuously operated inn in the U.S., built in 1797.

Facilities of Wayside Inn

General
  • Free Wi-Fi
  • Parking
  • Pets allowed
Dining
  • Breakfast

Policies

Wayside Inn applies these conditions to all bookings.
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Check-in
24 Sept 2026
Check-out
25 Sept 2026
Guests
2 guests

Adults:

2

Children:

0
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