Hotel Event venue

Wayside Inn

Experience historic charm at Wayside Inn, a refined 1797 hotel with period-inspired rooms, a cozy tavern, and a quaint wood-beamed restaurant. Ideal for history lovers and event seekers near Middletown, VA.

7783 Main St, Middletown, VA 22645, United States 4.4/5 (562 reviews)
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Quick Match

Is this stay right for your trip?

Discover if Wayside Inn fits your travel needs and style.

Best for

History enthusiasts Event celebrations Families

Travel style

Cultural trips Leisure & relaxation

Stay vibe

Historic atmosphere Charming & cozy Period-inspired decor

Good to know

No pool or fitness center Kid-friendly Free Wi-Fi & parking Check-in 15:00 / Check-out 11:00

About this stay

Nestled just off Route 11, the Wayside Inn stands as a refined reminder of 18th-century charm, dating back to 1797. This historic hotel offers period-inspired rooms filled with antiques that whisper stories of days gone by, blending comfort with a genuine sense of place. Visitors seeking a stay steeped in character will find solace in the carefully curated décor and inviting wood-beamed restaurant that invites relaxation and connection over thoughtfully crafted meals and drinks.

The inn’s quaint tavern and restaurant spaces present a range of atmospheres—from casual gatherings to intimate dinners—set against the backdrop of exposed beams and warm, historic textures. While there is no pool or fitness center, amenities such as free Wi-Fi, air conditioning, and accessible facilities ensure a practical and comfortable visit. Families are welcomed here, while pet owners will note the property does not accommodate pets.

Beyond the inn’s storied walls, the location offers rich exploration opportunities. Just a short drive away lies the Belle Grove Plantation with its grand manor house and sprawling grounds, and the Museum of the Shenandoah Valley, showcasing regional history and artistry. Golf enthusiasts can enjoy nearby courses like Blue Ridge Shadows Golf Club, while local wineries and historical tours provide enriching day trips.

Whether hosting an event or seeking an evocative base to explore Virginia’s landscapes and heritage, the Wayside Inn balances historic allure with warm hospitality and a relaxed pace.

Historic 1797 inn with period antiques Free Wi-Fi & air-conditioned comfort Wood-beamed restaurant & tavern ambiance Family-friendly with event venue spaces Near Belle Grove Plantation & cultural sites

What makes this stay special

A few reasons this stay stands out from the others.

Living History

Every corner reveals stories dating back over two centuries, from antique furnishings to the original wood beams, forging a genuine connection with the past.

Period-Inspired Rooms

Comfortable guest rooms thoughtfully furnished with timeless antiques transport visitors to another era without sacrificing modern conveniences.

Atmospheric Event Spaces

Quintessential historic charm meets diverse indoor and outdoor settings to create memorable celebrations—from weddings to intimate celebrations.

Gateway to Historic Exploration

Within easy reach of renowned regional attractions, this inn serves as a serene base for discovering plantations, museums, and scenic landscapes.

Amenities that matter

A full view of what's available — and what's not — so you can decide with confidence.

  • Free Wi-Fi
  • Free parking
  • Accessible
  • Air-conditioned
  • Business center
  • Kid-friendly
  • Restaurant
  • Bar
  • Smoke-free
  • Pool
  • Pet-friendly
  • Airport shuttle
  • Fitness center

Room photos

A look at the rooms you'll find at this stay.

Hotel room photo 1 Hotel room photo 2 Hotel room photo 3 Hotel room photo 4 Hotel room photo 5 Hotel room photo 6 Hotel room photo 7 Hotel room photo 8 Hotel room photo 9 Hotel room photo 10

Location and nearby places

Historic charm and convenient access to top attractions and airports in Middletown, VA.

  • Cedar Creek and Belle Grove National Historical Park 4.6 rating · 642 reviews
  • Belle Grove Plantation 2.2 miles away · 4.7 rating · 436 reviews
  • Museum of the Shenandoah Valley 4.8 rating · 1494 reviews
  • Dulles International Airport 1 hr 19 min by car
  • Ronald Reagan Washington National Airport 1 hr 20 min by car
  • Baltimore/Washington International Thurgood Marshall Airport (BWI) 1 hr 47 min by car
  • Laurel Ridge Community College 15 min walk
Located on Route 11, Wayside Inn offers easy access to historic sites, local dining, and major airports within a two-hour drive.

What the stay feels like

A short editorial tour through a typical day at Ocean View Resort.

Morning Calm

Soft light filters through antique windowpanes as the scent of fresh brewed coffee drifts from the cozy self-serve nook—a gentle start embraced by history’s embrace.

Afternoon Stories

Guided tours reveal hidden secrets: trap doors, original brickwork, and tales of spirited pasts, while warm conversations spill into the inviting tavern.

Evening Warmth

Gather around glowing tables beneath exposed beams to share a meal rich with local flavor and heartfelt hospitality, as soft music blends with laughter and candlelight.

Night Whispers

The quiet historic inn holds a mysterious allure—echoes of the past mingle with the night’s calm, inviting reflection and a touch of wonder before rest.

Traveler reviews

What recent guests say about their stay.

4.4
562 reviews
5
396
4
91
3
29
2
18
1
33
M
Michael Enders
May 21, 2026

"WOW WOW WOW! We have stayed in old Inns all over the world, and this may have been our BEST experience! The host Brittany and her staff were TOP NOTCH! They went out of there way to show us the history and details of the building and grounds! The place is UNREAL! We loved the room decor, comfort, history and location! We will be back MANY MANY more times, TRUST ME! 10 STARS!!"

M
Mike S
May 01, 2026

"This is an absolutely amazing. very old inn that is full of charm, character and a long history!! They will be reopening the restaurant in October. There are 5 separate dining areas from casual to formal. Two sitting rooms, a wedding venue and several outside seating areas. There are 21 rooms all with period antiques. The staff are just wonderful! Jessica gave us the full tour which we so appreciated. There are about 20 wineries within 30 minutes of here..."

R
Radley Kave
Apr 27, 2026

"My wife and I held a celebration dinner for our wedding here. The food was absolutely amazing! The best steak iv ever had! Environment is wonderful and friendly staff. Looking forward to returning."

P
P M
Apr 06, 2026

"We recently celebrated our wedding reception at the Wayside Inn, and it was nothing short of magical. This beautiful historic inn is full of character, charm, and timeless elegance—every corner of the property tells a story, and it provided the perfect setting for our special day. What truly set the experience apart was the amazing staff, especially Brittany, the property manager. From the very beginning, Brittany was attentive, organized, and incredibly kind. She guided us through the planning process with..."

F
Faye Cloven
Mar 25, 2026

"The Wayside Inn is a gem. From the warm, accommodating staff to the incredible atmosphere, it offers an experience unlike anything else in the area. Every corner of the inn feels special, with a real “if these walls could talk” kind of charm. That said, if you’re looking for perfectly uniform guest rooms, oversized TVs, or instant hot water the second you turn on the shower, this may not be your style. But if you appreciate character, history, and genuine..."

N
NYC Dapper Dan
Mar 06, 2026

"Came for the Ghost Tour. Jessica was great! Shared with us the rich history and paranormal experiences. Saw the prohibition speakeasy, trap door, original brick and wood, and even got goosebumps in the dining room. Felt like electricity..like I was being watched."

S
Stargazer (Night Sky)
Feb 17, 2026

"This is a lovely old historic inn. It is furnished with antiques and unique items. There are several rooms to hang out in and a cute little self-serve coffee/tea bar. The staff was super-friendly, helpful, and informative. The seasonal decorations were festive and spirited. Taking a point off for the room because there were some issues with the bedding. There was food stuck to the bedskirt, stains on the coverlet and crumbs on the night table - otherwise the room..."

A
Abror Kaiumov
Feb 15, 2026

"Thank you so much for the wonderful stay. The atmosphere of the hotel is truly historical, with very beautiful décor and pictures that reflect the charm of old times. The design is unique and full of character. The staff are extremely friendly and welcoming, the service is excellent. I am very, very happy that I had the chance to be your guest and truly enjoyed my stay."

Frequently asked questions

Quick answers to things travelers often ask about this stay.

Check-in is at 15:00 and check-out is at 11:00.
Yes, free parking and free Wi-Fi are available for guests.
No, the property does not allow pets.
Yes, the inn features an on-site restaurant and bar, plus nearby family restaurants like Clem's Kitchen.
Yes, Wayside Inn offers accessible facilities.
No, the hotel does not have a fitness center or pool.
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