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Dec 12 - Dec 14
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Inns in Middletown

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Recommended hotels in Middletown

Bar (on property)
Wayside Inn

Wayside Inn

3.5 star property
Middletown
9.2 out of 10, Wonderful, (416)
"Historic inn. "
United States
David
$89 nightly
The price is $98
Dec 8 - Dec 9
Total with taxes and fees
Wayside Inn
Breakfast area
Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2.0 star property
Middletown
5.8 out of 10, (299)
"I loved staying here!"
United States
Whitney
$62 nightly
The price is $68
Dec 14 - Dec 15
Total with taxes and fees
Econo Lodge Inn & Suites
Lobby
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1374)
"Excellent accommodations"
United States
Loretta
$72 nightly
The price is $78
Jan 5 - Jan 6, 2026
Total with taxes and fees
Microtel Inn & Suites by Wyndham Winchester
Snack bar
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (765)
"The hotel was clean and the staff was pleasant."
United States
Sherri
$81 nightly
The price is $88
Dec 24 - Dec 25
Total with taxes and fees
TRU By Hilton Winchester
Lobby
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
Winchester
8.8 out of 10, Excellent, (1002)
"Have stayed here multiple times -always good"
United States
Robert
$81 nightly
The price is $88
Jan 4 - Jan 5, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA
Lobby
Spark by Hilton Winchester

Spark by Hilton Winchester

3.0 star property
Winchester
9.0 out of 10, Wonderful, (1001)
"Great location close to restaurants "
United States
SILVIA
$75 nightly
The price is $85
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spark by Hilton Winchester
Exterior
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 star property
Winchester
9.4 out of 10, Exceptional, (1075)
"Very clean, helpful staff"
United States
Kathleen
$100 nightly
The price is $109
Dec 22 - Dec 23
Total with taxes and fees
Comfort Inn & Suites Winchester
Elevator
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 star property
Strasburg
8.2 out of 10, Very Good, (1005)
"Friendly Staff, clean room."
Canada
Frank
$71 nightly
The price is $79
Dec 23 - Dec 24
Total with taxes and fees
Ramada by Wyndham Strasburg/Shenandoah Valley
Lobby
Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal

2.0 star property
Front Royal
7.6 out of 10, Good, (1001)
"The staff was friendly and attentive. The room was clean. The breakfast was good, with pancakes, toast, cereal, juice, and coffee. Good location for visiting Shenandoah National Park."
United States
Teresa
$59 nightly
The price is $66
Dec 8 - Dec 9
Total with taxes and fees
Super 8 by Wyndham Front Royal
Exterior
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3.0 star property
Winchester
9.2 out of 10, Wonderful, (2217)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
$105 nightly
The price is $114
Dec 16 - Dec 17
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester
Exterior
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3.0 star property
Winchester
9.0 out of 10, Wonderful, (1004)
"Clean room, nicely furnished."
United States
Marilyn
$77 nightly
The price is $84
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
Exterior
Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

2.5 star property
Woodstock
9.0 out of 10, Wonderful, (1001)
"Rooms were clean. Pleasant and professional staff. Good breakfast."
United States
Lora
$82 nightly
The price is $92
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
2 restaurants, breakfast, lunch, dinner served; American cuisine
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1009)
"Wonderful stay - staff was friendly and knowledgeable about the goings on in town for the holidays which helped plan our trip can’t wait to go back"
United States
Jeanette
$127 nightly
The price is $143
Dec 14 - Dec 15
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel
Restaurant
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

3.0 star property
Winchester
9.0 out of 10, Wonderful, (912)
"comfortable room, amenities and staff"
United States
Prashant
$107 nightly
The price is $116
Dec 14 - Dec 15
Total with taxes and fees
Courtyard by Marriott Winchester
Pillowtop beds, desk, laptop workspace, blackout drapes
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 star property
Winchester
9.4 out of 10, Exceptional, (773)
"Clean room, courteous and professional staff. Great breakfast selections"
United States
Lauris
$107 nightly
The price is $117
Dec 14 - Dec 15
Total with taxes and fees
SpringHill Suites by Marriott Winchester
Lobby
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 star property
Winchester
7.8 out of 10, Good, (1000)
"The rooms were clean and the facility seemed safe and well maintained. The room had seen many patches and repairs and had a distinct smell. The indoor pool, “gym” and breakfast were a plus. "
United States
tyshia
$59 nightly
The price is $64
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sleep Inn & Suites Winchester near University
Lobby
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 star property
Winchester
8.6 out of 10, Excellent, (1078)
"Good price, good location "
United States
George
$68 nightly
The price is $74
Dec 22 - Dec 23
Total with taxes and fees
Travelodge by Wyndham Winchester
Exterior
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

2.5 star property
Winchester
9.0 out of 10, Wonderful, (797)
"Quick check in, clean room, friendly staff."
United States
Darcy
$93 nightly
The price is $101
Dec 11 - Dec 12
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester
Exterior
Quality Inn Winchester

Quality Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1006)
"Great stay"
United States
Jaron
$76 nightly
The price is $82
Dec 15 - Dec 16
Total with taxes and fees
Quality Inn Winchester
Suite, 1 Bedroom | In-room safe, desk, laptop workspace, blackout drapes
Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

2.5 star property
Winchester
8.8 out of 10, Excellent, (542)
"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
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.
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Top Middletown Hotel Reviews

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"Staff is fantastic and breakfast is always great. "
LESLIE 3-night trip
Posted 2 days ago
Holiday Inn Winchester Se-Historic Gateway by IHG

Find out more about Middletown

Middletown Inns information

Number of reviews
19,256
Accommodation
0 Inns
Lowest Price
$64
Highest Price
$143

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