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Wayside Inn

3.5 star property
Colonial hotel in Middletown with free parking

Choose dates to view prices

Photo gallery for Wayside Inn

Bar (on property)
15 - Bernstein Suite | Individually decorated, individually furnished, iron/ironing board
Interior detail
Exterior
Lobby sitting area

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Free WiFi
  • Air conditioning
  • Parking included
  • Business services

Explore the area

View in a map
7783 Main St, Middletown, VA, 22645
  • Place, Wayside Theater
    ‪2 min walk‬
  • Place, Cedar Creek Battlefield Foundation
    ‪2 min drive‬
  • Place, Cedar Creek and Belle Grove National Historical Park
    ‪2 min drive‬
  • Airport, Martinsburg, WV (MRB-Eastern West Virginia Regional)
    ‪32 min drive‬

Room options

View all photos for 01 - Jubal Early Stateroom

01 - Jubal Early Stateroom | Individually decorated, individually furnished, iron/ironing board

01 - Jubal Early Stateroom

  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for 02 - Reeves Stateroom

02 - Reeves Stateroom | Individually decorated, individually furnished, iron/ironing board

02 - Reeves Stateroom

  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for 03 - Cedar Creek Guest Room

03 - Cedar Creek Guest Room | Individually decorated, individually furnished, iron/ironing board

03 - Cedar Creek Guest Room

  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for 04 - Wilkenson Guest Room

04 - Wilkenson Guest Room | Individually decorated, individually furnished, iron/ironing board

04 - Wilkenson Guest Room

  • 1 bedroom
  • Sleeps 2
  • 2 Twin Beds

View all photos for 05 - Middletown Guest Room

05 - Middletown Guest Room | Individually decorated, individually furnished, iron/ironing board

05 - Middletown Guest Room

8.0 out of 10
Very good
(1 review)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for 06 - Lincoln Stateroom

06 - Lincoln Stateroom | Individually decorated, individually furnished, iron/ironing board

06 - Lincoln Stateroom

  • Sleeps 2
  • 1 King Bed

View all photos for 07 - Jefferson Guest Room

07 - Jefferson Guest Room | Individually decorated, individually furnished, iron/ironing board

07 - Jefferson Guest Room

8.8 out of 10
Excellent
(3 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for 08 - Taylor Guest Room

08 - Taylor Guest Room | Individually decorated, individually furnished, iron/ironing board

08 - Taylor Guest Room

8.0 out of 10
Very good
(1 review)
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for 09 - Harrison Guest Room

09 - Harrison Guest Room | Individually decorated, individually furnished, iron/ironing board

09 - Harrison Guest Room

  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for 11 - Tyler Guest Room

11 - Tyler Guest Room | Individually decorated, individually furnished, iron/ironing board

11 - Tyler Guest Room

10.0 out of 10
Exceptional
(2 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for 12 - Madison Stateroom

12 - Madison Stateroom | Individually decorated, individually furnished, iron/ironing board

12 - Madison Stateroom

8.0 out of 10
Very good
(1 review)
  • 1 bedroom
  • Sleeps 2
  • 2 Queen Beds

View all photos for 14 - Rhodes Suite

14 - Rhodes Suite | Individually decorated, individually furnished, iron/ironing board

14 - Rhodes Suite

10.0 out of 10
Exceptional
(1 review)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for 15 - Bernstein Suite

15 - Bernstein Suite | Individually decorated, individually furnished, iron/ironing board

15 - Bernstein Suite

10.0 out of 10
Exceptional
(1 review)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for 16 - Washington Stateroom

Individually decorated, individually furnished, iron/ironing board

16 - Washington Stateroom

  • 1 bedroom
  • Sleeps 2
  • 2 Double Beds

View all photos for 18 - Shenandoah Guest Room

18 - Shenandoah Guest Room | Individually decorated, individually furnished, iron/ironing board

18 - Shenandoah Guest Room

10.0 out of 10
Exceptional
(1 review)
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for 20 - Rutherford Stateroom

20 - Rutherford Stateroom | Individually decorated, individually furnished, iron/ironing board

20 - Rutherford Stateroom

  • 1 bedroom
  • Sleeps 2
  • 2 Large Twin Beds

View all photos for 21 - Hite Guest Room

21 - Hite Guest Room | Individually decorated, individually furnished, iron/ironing board

21 - Hite Guest Room

  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for 22 - Byrd Guest Room

22 - Byrd Guest Room | Individually decorated, individually furnished, iron/ironing board

22 - Byrd Guest Room

8.0 out of 10
Very good
(1 review)
  • Sleeps 2
  • 1 Queen Bed

View all photos for 23 - Wilson Guest Room

23 - Wilson Guest Room | Individually decorated, individually furnished, iron/ironing board

23 - Wilson Guest Room

10.0 out of 10
Exceptional
(1 review)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for 24 - Monroe Guest Room

24 - Monroe Guest Room | Individually decorated, individually furnished, iron/ironing board

24 - Monroe Guest Room

10.0 out of 10
Exceptional
(1 review)
  • 1 bedroom
  • Sleeps 2
  • 1 Double Bed

View all photos for 19 - Massanutten

19 - Massanutten | Individually decorated, individually furnished, iron/ironing board

19 - Massanutten

  • Sleeps 3
  • 1 Double Bed

View all photos for 17 - Lee Guest Room

Individually decorated, individually furnished, iron/ironing board

17 - Lee Guest Room

9.0 out of 10
Wonderful
(2 reviews)
  • Sleeps 3
  • 1 Double Bed

About the neighborhood

Middletown

Cedar Creek Battlefield Foundation is within 2 miles (3 km) of Wayside Inn while other popular attractions such as Belle Grove Plantation are within 3 miles (5 km). This 22-room hotel welcomes guests with conveniences like free in-room WiFi, free self parking, and coffee/tea in a common area.

What's nearby

  • Wayside Theater - 2 min walk - 0.1 miles
  • Cedar Creek Battlefield Foundation - 2 min drive - 1.5 miles
  • Cedar Creek and Belle Grove National Historical Park - 2 min drive - 1.5 miles
  • Front Royal Entrance Shenandoah National Park - 17 min drive - 15.4 miles
  • Skyline Caverns - 18 min drive - 16.5 miles

Getting around

  • Washington Dulles Intl. Airport (IAD) - 72 min drive

Restaurants

  • ‪McDonald's - ‬7 min drive
  • ‪Ciro's - ‬8 min drive
  • ‪Starbucks - ‬7 min drive
  • ‪McDonald's - ‬8 min drive
  • ‪Taco Bell - ‬7 min drive

About this property

Wayside Inn

Colonial hotel in Middletown with free parking
Wayside Inn features free WiFi in public areas, coffee in a common area, and a meeting room. You can take advantage of free parking if you drive. Additional amenities include a library, express check-out, and a terrace.
Guests can expect to find free WiFi and TVs with cable channels. Bathrooms have hair dryers and free toiletries. Ironing boards and wardrobes or closets are other standard amenities. Housekeeping is available on request.

Similar properties

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Ramada by Wyndham Strasburg/Shenandoah Valley
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  • Pet friendly
  • Parking included
  • Free WiFi
8.2 out of 10, Very Good, 1,002 reviews
$75 nightly
The price is $83
Nov 23 - Nov 24
Total with taxes and fees
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Property amenities

Internet

  • Available in all rooms: Free WiFi
  • In-room WiFi speed: 100+ Mbps (good for 1–2 people or up to 6 devices)
  • Available in some public areas: Free WiFi

Parking and transportation

  • Free uncovered self parking on site
  • Free extended parking on site
  • Free RV/bus/truck parking on site
  • Limited onsite parking
  • Onsite parking includes off-street options

Food and drink

  • Coffee and tea in common areas
  • Couples/private dining
  • Private picnics

Things to do

  • Books
  • Concerts/live shows
  • Evening entertainment
  • Library

Family friendly

  • High chair

Conveniences

  • Guidebooks

Guest services

  • Housekeeping (on request)
  • Proposal/romance packages
  • Wedding services

Business services

  • Meeting room

Outdoors

  • Garden
  • Outdoor entertainment area
  • Outdoor furniture
  • Picnic area
  • Terrace

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Handrails in stairways (33 inches high)
  • No elevator
  • Stair-free path to entrance
  • Thin carpet in room

More

  • 3 floors
  • Ballroom
  • Banquet hall
  • Built in 1742
  • Colonial architecture
  • Designated smoking areas
  • Fireplace in lobby
  • Reception hall

Room amenities

Bathroom

  • Bathtub or shower
  • Free toiletries
  • Hair dryer
  • Towels provided

Entertainment

  • TV with cable channels

More

  • Air conditioning
  • Heating
  • Individual decor
  • Individual furnishings
  • Iron/ironing board

Policies

Check-in

Check-in start time: 3:00 PM; Check-in end time: 8:00 PM
Early check-in subject to availability
Early check-in fee: USD 50.00
Minimum check-in age: 18

Check-out

Check-out before 11:00 AM
Late check-out subject to availability
Late check-out fee: USD 50.00
Express check-out available

Special check-in instructions

The front desk is open Monday to Thursday (9:00 AM – 8:00 PM), Friday to Saturday (9:00 AM – 9:00 PM), and Sunday to Sunday (9:00 AM – 8:00 PM)
Guests planning to arrive outside of normal check-in hours must contact the property in advance for check-in instructions and an access code; front desk staff will greet guests on arrival at the property
To make arrangements for check-in please contact the property at least 72 hours before arrival using the information on the booking confirmation
Prior to arrival, you must complete online registration via a secure link
If you are planning to arrive after 3:00 PM please contact the property in advance using the information on the booking confirmation

Access methods

Access code, staffed front desk

Pets

  • Service animals exempt from fees

Children and extra beds

  • Rollaway/extra beds are available for USD 25.0 per day

Property payment types

Important information

Fees

You'll be asked to pay these charges at the property:

  • Cleaning fee: USD 5.00 per accommodation, per night
  • Bed sheets fee: USD 5.00 per accommodation, per night

These are all of the charges provided to us by the property.

Optional extras

These fees and deposits will be charged at check-in, check-out, or the time of service.

  • Early check-in fee: USD 50.00 (subject to availability)
  • Late check-out fee: USD 50.00 (subject to availability)
  • Housekeeping fee: USD 5.00 per night
  • Rollaway bed fee: USD 25.0 per day

This list may not be comprehensive. Fees and deposits might not include tax and are subject to change.

You need to know

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
  • Check-in: 3:00 PM—-8:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 18
Driving? This property offers free self parking, along with free RV, bus, and truck parking.

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards, debit cards, and cash.
  • Onsite safety features include a fire extinguisher, a security system, and a first aid kit.

Additional information about polices, regulations, and more:

  • There are no elevators.
  • No cribs or infant beds are available.

Property is also known as

Wayside Inn Middletowne
Wayside Middletowne
Wayside Inn Middletown
Wayside Middletown
Wayside Inn Middletown
Wayside Middletown
Inn Wayside Inn Middletown
Middletown Wayside Inn Inn
Wayside Inn Middletowne
Inn Wayside Inn
Wayside
Wayside Inn Hotel
Wayside Inn Middletown
Wayside Inn Hotel Middletown

Frequently asked questions

What's there to see around Wayside Inn?

This hotel is located in Middletown, just steps from Wayside Theater. You'll also find Cedar Creek Battlefield Foundation and Shenandoah River within a short drive.

How much does it cost to stay at Wayside Inn?

As of Nov 19, 2025, prices found for a 1-night stay for 2 adults at Wayside Inn on Nov 23, 2025 start from $120.49, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Will I be able to park at Wayside Inn?

Yes, self parking and long-term parking are offered for free at the hotel. Though parking is limited, free RV/bus/truck parking is also available.

Does Wayside Inn include a casino on the premises?

No, Wayside Inn doesn't have a casino.

Will I find an indoor pool at Wayside Inn?

No, there is no indoor pool at this hotel.

What will couples enjoy most about a stay at Wayside Inn?

There are plenty of amenities for couples at this hotel, including private dining, proposal/romance packages, and private picnics.

Are there hot tubs at Wayside Inn?

No, there isn't a spa tub at this hotel.

Does Wayside Inn have a restaurant that serves breakfast?

No, Wayside Inn doesn't have a restaurant that serves breakfast.

Will Wayside Inn allow pets to stay for free?

No, pets aren't allowed at Wayside Inn though service animals are welcome.

Are there connecting rooms at Wayside Inn?

No, this hotel doesn't feature connecting guestrooms.

Are there rooms with balconies that I can book at Wayside Inn?

No, there aren't any guestrooms with balconies at Wayside Inn.

Does Wayside Inn host weddings?

There are wedding services available at Wayside Inn if that's in your vacation plans.

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