Winchester Hotel Guide - Romantic Hotels in Winchester, Virginia

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Romantic Hotels

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winchester romantic hotels

Pillow-top beds, desk, laptop workspace, blackout curtains
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, (788)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is €99
includes taxes & fees
18 Jan - 19 Jan 2026
SpringHill Suites by Marriott Winchester
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, (1000)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is €108
includes taxes & fees
11 Jan - 12 Jan 2026
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, (1000)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is €91
includes taxes & fees
31 Dec - 1 Jan 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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, (1005)
"Great hotel!"
United States
CHARLES
The price is €122
includes taxes & fees
1 Jan - 2 Jan 2026
The George Washington Hotel, A Wyndham Grand Hotel
Bar (on property)
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (418)
"Historic inn. "
United States
David
The price is €76
includes taxes & fees
28 Dec - 29 Dec
Wayside 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
The price is €214
includes taxes & fees
4 Jan - 5 Jan 2026
L'Auberge Provencale Inn & Restaurant
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, (512)
"Great hotel"
United States
DONNA D
The price is €97
includes taxes & fees
31 Dec - 1 Jan 2026
Hilton Garden Inn Winchester
Exterior
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (95)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is €249
includes taxes & fees
20 Jan - 21 Jan 2026
Glen Gordon Manor
Cookware/dishes/utensils
The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond
Linden
10.0 out of 10, Exceptional, (33)
"It was the perfect home away from home in a place that allowed our little family to take a breath of nature and just be. Close enough to many fun adventures. The amenities provided on the property also kept us very busy!"
United States
Brena H.
The price is €578
includes taxes & fees
7 Jan - 8 Jan 2026
The Pond Cabin: Hot Tub & Stocked Pond
Outdoor dining
Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool
bluemont
9.8 out of 10, Exceptional, (262)
"We had such a wonderful time at this gorgeous house! It was clean, comfortable, spacious and very relaxing. Our group had kids and adults of all ages and everyone had a fantastic time. The brewery next door is an added bonus, and we didn’t have any issues with noise or crowds. We will definitely stay here again."
United States
Laura D.
The price is €1,475
includes taxes & fees
15 Jan - 16 Jan 2026
Breathtaking View with an Indoor Pool
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.
View all properties

Top Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"It would be nice if they had a business center that was actually a business center and not a storage room"
Denise 1-night trip
Posted 3 days ago
The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"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. "
Jordyn 1-night trip
Posted 3 days ago
La Quinta Inn & Suites by Wyndham Winchester

Frequently asked questions

Searching for romantic hotels in Winchester?
If you and your partner need a romantic holiday, we've got just the thing. Couples choose Winchester for its scenic landscape and top-notch restaurants. If you're hoping to explore some cultural attractions while you're in town, Bright Box Theater or Winchester Little Theater make for a fun date night. Whether you'd like to sip a glass of champagne or lounge around in luxurious bedding, there are 4 hotels and other accommodations in Winchester.
What's the best accommodation for a couple going to Winchester?
Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed is a favourite guest house for couples, and features a garden and laundry facilities. Other good choices for your romantic getaway include Secret Gardens Carriage House and ANS Inn has clean, spacious rooms located on 5 acres with little traffic..
When is the best time of year for a romantic getaway to Winchester?
If you're looking forward to lots of outings with your partner, take a look at these details about year-round temperatures in Winchester: The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.
What is there to do in Winchester?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Winchester. If you're hoping to see some of the area's cultural attractions, you and your partner will love Winchester for its interesting historical sites and major shopping area. You might think about stopping by Bright Box Theater, Shenandoah Valley Discovery Museum or Patsy Cline Historic House while you're seeing the sights.
What's the best way to get to Winchester and around town during my romantic getaway?
This information about transportation options in Winchester might help your romantic getaway go off without a hitch: If you're looking to fly to Winchester, the closest major airport is in Martinsburg, WV (MRB-Eastern West Virginia Regional), located 18 mi (28.9 km) from the city centre. If you'd like to venture out around the area, you may want a rental car for your journey.