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Find Romantic Hotels in Middletown, VA

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Check availability on Middletown Romantic Hotels

Our top choices for Middletown romantic hotels

Bar (on property)
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (416)
"Historic inn. "
United States
David
The price is NT$2,246
NT$2,789 total
includes taxes & fees
Dec 21 - Dec 22
Wayside Inn
Pillowtop beds, desk, laptop workspace, blackout drapes
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (782)
"The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. "
United States
Yolanda
The price is NT$3,341
NT$3,635 total
includes taxes & fees
Dec 21 - Dec 22
SpringHill Suites by Marriott Winchester
2 restaurants, breakfast, lunch, dinner served; American cuisine
The George Washington Hotel, A Wyndham Grand Hotel

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, (1010)
"Great hotel!"
United States
CHARLES
The price is NT$3,951
NT$4,476 total
includes taxes & fees
Dec 23 - Dec 24
The George Washington Hotel, A Wyndham Grand Hotel
Lobby
Hampton Inn Front Royal

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1002)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is NT$3,344
NT$3,722 total
includes taxes & fees
Dec 22 - Dec 23
Hampton Inn Front Royal
Bar (on property)
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1003)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is NT$3,044
NT$3,357 total
includes taxes & fees
Dec 22 - Dec 23
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Exterior
Holiday Inn Express Woodstock-Shenandoah Valley by IHG

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, (1000)
"Rooms were clean. Pleasant and professional staff. Good breakfast."
United States
Lora
The price is NT$2,792
NT$3,135 total
includes taxes & fees
Jan 11 - 2026/1/12
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
Indoor pool
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (510)
"Great hotel"
United States
DONNA D
The price is NT$2,995
NT$3,393 total
includes taxes & fees
Dec 22 - Dec 23
Hilton Garden Inn Winchester
Terrace/patio
L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
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
The price is NT$9,378
NT$10,344 total
includes taxes & fees
Dec 17 - Dec 18
L'Auberge Provencale Inn & Restaurant
Premier Villa, 1 King Bed, Mountain View | Terrace/patio
White Moose Inn

White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (147)
"Amazing trip! "
United States
Rebecca
White Moose Inn
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Comfortable and clean room."
Linda 1-night trip
Posted 7 days ago
La Quinta Inn & Suites by Wyndham Winchester

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Frequently asked questions

Searching for romantic hotels in Middletown?
If you and your partner need a romantic escape, we've got just the ticket. Our guests also enjoy Middletown for its bars, restaurants, and historic landmarks. If you'd like to explore some of the area's notable sights, you might make a stop by Belle Grove Plantation, Shenandoah River, or Wayside Theater. If you're interested in staying close to a particular destination, you can sort by neighborhood or distance to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Middletown?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Middletown: The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Middletown is 43 inches.
What is there to do in Middletown?
There's nothing better than wandering around a new place with your sweetheart, so consider checking out all that Middletown has to offer. Couples looking for a little of everything will enjoy Middletown for its bars, restaurants, and historic landmarks. You might think about stopping by Belle Grove Plantation, Shenandoah River, or Wayside Theater while you're seeing the sights.
What's the best way to get to Middletown and around town during my romantic getaway?
This information about transportation options in Middletown might help your romantic trip go off without a hitch: The closest major airport is Martinsburg, WV (MRB-Eastern West Virginia Regional), located 30.4 mi (48.9 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.