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Find Romantic Hotels in Middletown, VA from $98

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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
$89 nightly
The price is $98
Dec 14 - Dec 15
Total with taxes and fees
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
9.6 out of 10, Exceptional, (777)
"The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. "
United States
Yolanda
$107 nightly
The price is $117
Dec 21 - Dec 22
Total with taxes and fees
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, (1006)
"Great hotel!"
United States
CHARLES
$127 nightly
The price is $143
Dec 18 - Dec 19
Total with taxes and fees
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
$107 nightly
The price is $119
Dec 21 - Dec 22
Total with taxes and fees
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, (1001)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
$98 nightly
The price is $108
Dec 18 - Dec 19
Total with taxes and fees
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)
"Excellent hotel. Rooms were clean, food was good. Staff was great. "
United States
Kathy
$100 nightly
The price is $112
Dec 28 - Dec 29
Total with taxes and fees
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
9.0 out of 10, Wonderful, (508)
"Great hotel"
United States
DONNA D
$95 nightly
The price is $108
Dec 22 - Dec 23
Total with taxes and fees
Hilton Garden Inn Winchester
Terrace/patio
Large Glamper w/ Hot Tub and full bathroom-sleep 6

Large Glamper w/ Hot Tub and full bathroom-sleep 6

Large Glamper w/ Hot Tub and full bathroom-sleep 6
Capon Bridge
9.8 out of 10, Exceptional, (24)
"We absolutely loved this place! The glamper had everything we needed and more! The hot tub was super relaxing and the host is super responsive! Would definitely stay here again in the future."
United States
Anonymous traveler
$169 nightly
The price is $188
Dec 14 - Dec 15
Total with taxes and fees
Large Glamper w/ Hot Tub and full bathroom-sleep 6
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
$342 nightly
The price is $369
Jan 2 - Jan 3, 2026
Total with taxes and fees
White Moose Inn
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
$287 nightly
The price is $317
Dec 15 - Dec 16
Total with taxes and fees
L'Auberge Provencale Inn & Restaurant
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 3 days ago
La Quinta Inn & Suites by Wyndham Winchester

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.

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