Find hotels near Wayside Theater, Middletown from $74

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Our top choices for Wayside Theater hotels

Wayside Inn

Wayside Inn
3.5 star property
< 0.1 mi from Wayside Theater
9.2 out of 10, Wonderful, (418)
"Historic inn. "
United States
David
$89 nightly
The price is $98
Dec 28 - Dec 29
Total with taxes and fees
Wayside Inn

Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
0.5 mi from Wayside Theater
5.8 out of 10, (299)
"I loved staying here!"
United States
Whitney
$69 nightly
The price is $76
Dec 25 - Dec 26
Total with taxes and fees
Econo Lodge Inn & Suites Middletown - Winchester South

TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
6.6 mi from Wayside Theater
9.6 out of 10, Exceptional, (556)
"Very good overall experience."
United States
Douglas
$120 nightly
The price is $132
Dec 29 - Dec 30
Total with taxes and fees
TownePlace Suites by Marriott Front Royal

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
7.6 mi from Wayside Theater
9.4 out of 10, Exceptional, (1090)
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
$97 nightly
The price is $106
Jan 5 - Jan 6, 2026
Total with taxes and fees
Comfort Inn & Suites Winchester

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 star property
3.6 mi from Wayside Theater
9.0 out of 10, Wonderful, (1000)
"Great stay."
United States
Kenneth
$113 nightly
The price is $126
Dec 29 - Dec 30
Total with taxes and fees
Fairfield Inn & Suites Strasburg Shenandoah Valley

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
10.4 mi from Wayside Theater
9.6 out of 10, Exceptional, (174)
"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
$211 nightly
The price is $233
Jan 4 - Jan 5, 2026
Total with taxes and fees
L'Auberge Provencale Inn & Restaurant

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
5.9 mi from Wayside Theater
9.0 out of 10, Wonderful, (1000)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
$98 nightly
The price is $108
Dec 31 - Jan 1, 2026
Total with taxes and fees
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
6.6 mi from Wayside Theater
9.0 out of 10, Wonderful, (1000)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
$114 nightly
The price is $127
Jan 11 - Jan 12, 2026
Total with taxes and fees
Hampton Inn Front Royal

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
11.3 mi from Wayside Theater
9.2 out of 10, Wonderful, (2233)
"The place was clean, super friendly front desk staff, SO pet friendly with such a reasonable pet fee, and overall reasonable rate. Would 100% stay here again if I came back through this town. "
United States
Jordyn
$99 nightly
The price is $107
Dec 28 - Dec 29
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
7.8 mi from Wayside Theater
8.8 out of 10, Excellent, (1001)
"Have stayed here multiple times -always good"
United States
Robert
$83 nightly
The price is $90
Jan 18 - Jan 19, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
4.1 mi from Wayside Theater
8.4 out of 10, Very Good, (1000)
"Breakfast was delicious "
United States
Robert
$71 nightly
The price is $79
Jan 1 - Jan 2, 2026
Total with taxes and fees
Ramada by Wyndham Strasburg/Shenandoah Valley

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
10.8 mi from Wayside Theater
9.0 out of 10, Wonderful, (1000)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
$85 nightly
The price is $92
Jan 1 - Jan 2, 2026
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
11.2 mi from Wayside Theater
9.0 out of 10, Wonderful, (1002)
"The place is spotless, comfortable and quiet. Very convenient as well, right off of 81"
United States
Michael
$83 nightly
The price is $94
Dec 31 - Jan 1, 2026
Total with taxes and fees
Spark by Hilton Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
12 mi from Wayside Theater
9.0 out of 10, Wonderful, (919)
"comfortable room, amenities and staff"
United States
Prashant
$107 nightly
The price is $116
Dec 31 - Jan 1, 2026
Total with taxes and fees
Courtyard by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
11 mi from Wayside Theater
9.0 out of 10, Wonderful, (800)
"Quick check in, clean room, friendly staff."
United States
Darcy
$93 nightly
The price is $101
Dec 27 - Dec 28
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
4.9 mi from Wayside Theater
8.2 out of 10, Very Good, (807)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
$74 nightly
The price is $81
Dec 31 - Jan 1, 2026
Total with taxes and fees
Holiday Inn Express Winchester South-Stephens City by IHG

Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG
2.5 star property
11.4 mi from Wayside Theater
8.8 out of 10, Excellent, (545)
"Very clean room, excellent staff!!!"
United States
James
$78 nightly
The price is $85
Jan 3 - Jan 4, 2026
Total with taxes and fees
Candlewood Suites Winchester by IHG

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
11.3 mi from Wayside Theater
9.0 out of 10, Wonderful, (1001)
"Staff, clean room, very comfortable bed!"
United States
Terri
$102 nightly
The price is $115
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn Winchester-University/Mall Area

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
11.2 mi from Wayside Theater
8.8 out of 10, Excellent, (512)
"Great hotel"
United States
DONNA D
$101 nightly
The price is $114
Dec 31 - Jan 1, 2026
Total with taxes and fees
Hilton Garden Inn Winchester

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
11.2 mi from Wayside Theater
8.6 out of 10, Excellent, (1085)
"Hotels well Located off 81 for a nice pull Off and overnight stay. Staff is friendly and helpful and rooms comfortable and quiet. "
United States
Stefanie
$68 nightly
The price is $74
Jan 14 - Jan 15, 2026
Total with taxes and fees
Travelodge by Wyndham Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Wayside Theater Hotel Reviews

Hotels near other Wayside Theater attractions

Frequently asked questions

What hotels are within walking distance to Wayside Theater?
Discover the perfect stay near Wayside Theater with these top-rated options that offer both comfort and charm.

Wayside Inn

Wayside Inn is just a minute's walk from Wayside Theater, with an impressive review rating of 9.2 and a cozy 3.5-star atmosphere. Guests appreciate the beautiful garden and terrace, perfect for relaxation. The inn also features romantic dining options and evening entertainment to enhance the stay. With free self-parking and the option for early check-in, this charming historic hotel is a fantastic choice for travelers wishing to enjoy a unique experience close to the theater.
How much is a hotel near Wayside Theater?
Staying near Wayside Theater is a treat, with plenty of hotels from $74 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, especially in peak season. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a vacation during weekends or around public holidays.
What are the most popular family-friendly hotels near Wayside Theater?
Finding the perfect family-friendly stay near Wayside Theater can enhance your experience in Middletown. Here are some top-rated hotels that cater to families, ensuring a comfortable and enjoyable visit.

Wayside Inn

Wayside Inn is a charming 3.5-star hotel located just a minute's walk from Wayside Theater. With a review rating of 9.2, this hotel is equipped with family-friendly amenities such as free rollaway beds and kids' meals, ensuring a delightful stay for travelers of all ages. Families can enjoy the garden area for picnics and unwind on the terrace after a day of exploring.

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley is a family-friendly retreat just 3.9 miles from Wayside Theater, a review rating of 9.0. Families will appreciate the indoor pool and free buffet breakfast, as well as the convenience of microwaves in the rooms. The hotel also provides spacious suites, ideal for larger families looking for extra comfort.

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley is conveniently situated 4.5 miles from Wayside Theater, offering a solid review rating of 8.2. This hotel features connecting rooms and daily housekeeping, making it an excellent choice for families. Guests can take advantage of the free breakfast and enjoy the arcade game room, perfect for keeping the kids entertained.
What are the best affordable hotels near Wayside Theater?
For those seeking the best affordable hotels near Wayside Theater, there are excellent options that combine comfort with budget-friendly amenities.

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley is a welcoming choice located just 3.9 miles from Wayside Theater. Rated by travelers with an impressive 9.0, this hotel offers free daily breakfast, a refreshing indoor pool, and complimentary WiFi. Guests can also enjoy spacious suites featuring a separate living room and accessible fitness facilities, making it perfect for families and groups.

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley is situated 4.5 miles from Wayside Theater and boasts a solid review rating of 8.2. This hotel is family-friendly, offering free cribs and breakfast on weekends. Additional amenities include free WiFi, ample parking options, and nearby outdoor activities like hiking and skiing, ensuring a memorable stay for adventurers and families alike.
Are there any hotels with pools close to Wayside Theater?
For travelers seeking a refreshing stay near Wayside Theater, there are excellent hotels featuring inviting pools to enjoy during your visit.

Fairfield Inn & Suites Strasburg Shenandoah Valley

Just 3.9 miles from Wayside Theater, the Fairfield Inn & Suites Strasburg Shenandoah Valley is a top choice for those looking for hotels with pools. Rated by travelers at an impressive 9.0, this 3-star hotel offers an indoor pool that is accessible to all travelers, perfect for a relaxing swim after a day of exploring. Guests can also enjoy complimentary breakfast options, including a hearty buffet, as well as amenities like a fitness center, free self-parking, and spacious suites with living areas and microwaves.
What are the best pet-friendly hotels near Wayside Theater?
For travelers seeking pet-friendly accommodations near Wayside Theater, you'll find excellent options that welcome your furry friends while providing a cozy stay.

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley is just 4.5 miles from Wayside Theater and comes highly rated with a review rating of 8.2. This hotel is perfect for pet owners, offering amenities such as in-room pet accommodations and service animal provisions. Guests can enjoy complimentary breakfast and access to fitness facilities, ensuring a pleasant stay. Additionally, the hotel features free self-parking and electric car charging stations, catering to varying travel needs.
Can I book a fully refundable hotel close to Wayside Theater?
Most bookings on Expedia are refundable if canceled within 24-48 hours of arrival, though this depends on the hotel's individual cancellation policy, which you should check in your booking confirmation. If free cancellation is available, you can cancel directly through your Expedia account by going to "My Trips" and selecting your reservation. To find fully refundable hotel options, simply enter "Wayside Theater", set your travel dates, and use the "Fully refundable" filter under "Deals & Discounts" on the results page. Alternatively, explore deals with free cancellation options on Expedia.
Can I find Expedia discounts for hotels near Wayside Theater?
To look for discounts on hotels near Wayside Theater, join One Key™—our free travel rewards program. One Key members always get our best prices and earn OneKeyCash™* on eligible bookings for every dollar spent. Another way to save is by bundling your hotel and flights together on Expedia.

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