A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Check availability on Winchester Romantic Hotels

Our top choices for Winchester romantic hotels

A courtyard with a fountain, tables with white tablecloths, and brick buildings.

1. 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, (1,003 reviews)
"Always great place and the old nostalgic look is the best"
United States
Christophe
The price is ￥20,831
￥23,601 total
includes taxes & fees
Nov 23 - Nov 24
The George Washington Hotel, A Wyndham Grand Hotel
A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".

2. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (1,002 reviews)
"Clean room, great staff, good parking and free breakfast"
United States
Albert
The price is ￥10,388
￥11,770 total
includes taxes & fees
Nov 29 - Nov 30
Spark by Hilton Winchester
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

3. 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, (2,268 reviews)
"Great place to stay the night after a long drive"
United States
lucy
The price is ￥14,803
￥16,475 total
includes taxes & fees
Dec 6 - Dec 7
La Quinta Inn & Suites by Wyndham Winchester
A modern hotel lobby with a central dining area, a reception desk, and a large window providing natural light.

4. Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (964 reviews)
"The breakfast was delicious, it was very welcoming very clean best ever had at motel"
United States
Elizabeth
The price is ￥16,900
￥19,147 total
includes taxes & fees
Nov 21 - Nov 22
Hampton Inn Winchester N/Conference Center, VA
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.

5. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (975 reviews)
"Great place to stay in Winchester."
United States
Thomas
The price is ￥14,803
￥16,476 total
includes taxes & fees
Nov 23 - Nov 24
Fairfield Inn & Suites by Marriott Winchester
A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

6. Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
"We had an amazing stay and will be back! The rooms were clean and comfy and staff were very helpful."
United States
Jessica
The price is ￥17,111
￥19,045 total
includes taxes & fees
Nov 23 - Nov 24
Courtyard by Marriott Winchester
A buffet with multiple self-service stations, including omelets and other prepared foods.

7. Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
2.5 star property
Winchester
9.0 out of 10, Wonderful, (871 reviews)
"Very clean comfortable bed good breakfast"
United States
David
The price is ￥14,870
￥16,551 total
includes taxes & fees
Dec 12 - Dec 13
Holiday Inn Express Hotel & Suites Winchester by IHG
A modern interior with a geometric ceiling design, recessed lighting, and hanging spherical light fixtures.

8. Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (562 reviews)
"Great location."
United States
Mark
The price is ￥18,877
￥21,388 total
includes taxes & fees
Nov 23 - Nov 24
Hilton Garden Inn Winchester
A hotel room with a bed, a desk, a chair, a sofa, a microwave, a refrigerator, and a television.

9. Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG
2.5 star property
Winchester
8.8 out of 10, Excellent, (659 reviews)
"Nice place to stay. Convenient for our travels."
United States
marilyn
The price is ￥12,782
￥14,226 total
includes taxes & fees
Nov 29 - Nov 30
Candlewood Suites Winchester by IHG
A hotel lobby with seating, a reception desk, and a refrigerated display.

10. TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (536 reviews)
"Always a great place to land!! Love the location!! Great walking areas, a grocery store and lots of restaurants within walking distance!! Many many good wineries as well!!"
United States
Lori
The price is ￥18,062
￥20,103 total
includes taxes & fees
Nov 23 - Nov 24
TownePlace Suites by Marriott Winchester
A modern living room with a sofa, armchair, dining table, and chairs. There is a TV mounted on the wall and a small table with a lamp.

11. Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,077 reviews)
"Clean room, good staff, good location"
United States
Gregory
The price is ￥11,184
￥12,336 total
includes taxes & fees
Dec 1 - Dec 2
Travelodge by Wyndham Winchester
A lobby with a green wall, a reception desk, and seating area with sofas and armchairs.

12. Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.6 out of 10, Good, (1,007 reviews)
"I had a good stay and staff was friendly"
United States
Leah
The price is ￥9,458
￥10,526 total
includes taxes & fees
Dec 6 - Dec 7
Sleep Inn & Suites Winchester near University
A hotel room with a bed, a desk, a chair, a TV, and a painting on the wall.

13. Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA
2.0 star property
Winchester
7.4 out of 10, Good, (1,004 reviews)
"great staff"
United States
alias
The price is ￥10,783
￥12,000 total
includes taxes & fees
Nov 30 - Dec 1
Red Roof Inn Winchester, VA
A snack and beverage display area with shelves stocked with various snacks and a refrigerated section with beverages.

14. Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
"I like the cleanliness of the room and the breakfast options."
United States
Henedina
The price is ￥14,678
￥16,631 total
includes taxes & fees
Dec 6 - Dec 7
Hampton Inn Winchester-University/Mall Area
An indoor swimming pool with clear water, surrounded by windows and potted plants.

15. APM Inn & Suites

APM Inn & Suites
2.0 star property
Winchester
7.0 out of 10, Good, (532 reviews)
"Staff was friendly and helpful"
United States
Verna
The price is ￥8,806
￥9,978 total
includes taxes & fees
Dec 6 - Dec 7
APM Inn & Suites
A hotel room with two beds, a nightstand, a lamp, and two framed waterfall paintings on the wall.

16. Super 8 by Wyndham Winchester VA

Super 8 by Wyndham Winchester VA
2.0 star property
Winchester
6.2 out of 10, (674 reviews)
"The “breakfast “ was underwhelming to say the least. Otherwise the staff was pleasant and the room more than adequate."
Canada
Donald
The price is ￥10,225
￥11,380 total
includes taxes & fees
Nov 23 - Nov 24
Super 8 by Wyndham Winchester VA
A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.

17. Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
10.0 out of 10, Exceptional, (99 reviews)
"Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent."
United States
Alexander and Judith
The price is ￥47,771
￥55,080 total
includes taxes & fees
Nov 16 - Nov 17
Glen Gordon Manor
An outdoor seating area with a fire feature, wicker furniture, and a building with multiple windows.

18. TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
Front Royal
9.6 out of 10, Exceptional, (619 reviews)
"Cleaned, maintained hotel near many conveniences."
United States
JoEllen
The price is ￥21,569
￥24,110 total
includes taxes & fees
Nov 17 - Nov 18
TownePlace Suites by Marriott Front Royal
A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.

19. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,153 reviews)
"Convenient to the highway and reasonably priced."
United States
Donna S.
The price is ￥14,803
￥16,475 total
includes taxes & fees
Nov 23 - Nov 24
Comfort Inn & Suites Winchester
A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.

20. Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,004 reviews)
"Great hotel"
Canada
Emmett
The price is ￥12,096
￥13,462 total
includes taxes & fees
Nov 22 - Nov 23
Quality Inn 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.
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Top Winchester Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Winchester?
If you and your partner need a romantic escape, we'd like to help you plan for it. 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 get a couple's massage or watch the sunset from your balcony, there are 3 hotels and other accommodations in Winchester.
What's the best hotel for a couple visiting Winchester?
Delightful and Serene Hundred Year Old Sweet Space Among the Gardens is a favorite guesthouse for couples, and features a garden and laundry facilities. Another good option for a romantic stay is Peaceful Secret Gardens Tiny Home - A space to relax and get away from it all..
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, check out these details about year-round temperatures in Winchester: 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 Winchester is 46 inches.
What is there to do in Winchester?
There's nothing better than wandering around 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 trip get off to a smooth start: If you're looking to fly to Winchester, the closest major airport is Martinsburg, WV (MRB-Eastern West Virginia Regional), located 18 mi (28.9 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.