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

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Winchester romantic hotels

A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.

1. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,147 reviews)
"Nice hotel. I would stay here again."
United States
Kenneth
The price is ￥15,818
￥17,605 total
includes taxes & fees
Nov 22 - Nov 23
Comfort Inn & Suites Winchester
A courtyard with a fountain, tables with white tablecloths, and brick buildings.

2. 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, (1,000 reviews)
"Always great place and the old nostalgic look is the best"
United States
Christophe
The price is ￥20,534
￥23,265 total
includes taxes & fees
Nov 8 - Nov 9
The George Washington Hotel, A Wyndham Grand Hotel
A room with a dining table and chairs, a bed, and a kitchen area visible through an open doorway.

3. ANS Inn & Suites

ANS Inn & Suites
2.0 star property
Winchester
7.4 out of 10, Good, (77 reviews)
"Lola e to cook dinner and eat it! Nice staff"
United States
Christopher
The price is ￥10,465
￥12,483 total
includes taxes & fees
Oct 29 - Oct 30
ANS Inn & Suites
A cozy living room with a fireplace, patterned chairs, and a dining area with wooden furniture.

4. Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (458 reviews)
"We very much enjoyed our night at the Inn. Historic, charming, unique. The people we met were attentive and friendly. Our room was clean and quiet throughout the night. The onsite restaurant served delicious food both at dinner and breakfast."
United States
Susan
The price is ￥10,066
￥12,676 total
includes taxes & fees
Nov 28 - Nov 29
Wayside Inn
A room with a dining table and chairs, a bed, and a kitchen area visible through an open doorway.

5. ANS Inn has clean, spacious rooms located on 5 acres with little traffic.

ANS Inn has clean, spacious rooms located on 5 acres with little traffic.
Winchester
The price is ￥9,527
￥25,293 total
includes taxes & fees
Oct 29 - Oct 30
ANS Inn has clean, spacious rooms located on 5 acres with little traffic.
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

6. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.4 out of 10, Very good, (6 reviews)
"Loved being so close to the old town; was able to walk to a lot of places. Great to have an assigned parking spot in a lot behind the building. Enjoyed staying here a lot!"
United States
Leslie L.
The price is ￥21,803
￥37,054 total
includes taxes & fees
Nov 15 - Nov 16
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A covered porch with white columns, a bench, and hanging flower baskets.

7. L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.4 out of 10, Exceptional, (180 reviews)
"Restaurant and bar are closed Mondays and Tuesdays. Expect barebones staffing and no food or drinks. Felt like staying at a strangers empty house."
United States
Henry
The price is ￥45,501
￥50,188 total
includes taxes & fees
Nov 2 - Nov 3
L'Auberge Provencale Inn & Restaurant
A hotel room with a large bed, a bathroom with a bathtub, and a framed picture on the wall.

8. Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 star property
Front Royal
6.4 out of 10, (1,001 reviews)
"Great breakfast nice room"
Netherlands
pieter
The price is ￥9,266
￥10,314 total
includes taxes & fees
Nov 15 - Nov 16
Baymont by Wyndham Front Royal Near Shenandoah National Park
A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.

9. Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 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 ￥44,079
￥50,824 total
includes taxes & fees
Nov 16 - Nov 17
Glen Gordon Manor
A spacious living room with a fireplace, a dining area with a bench, and a large sliding glass door leading to an outdoor patio.

10. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.6 out of 10, Exceptional, (8 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
The price is ￥22,119
￥61,342 total
includes taxes & fees
Nov 3 - Nov 4
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

8/10 Good
"There was no hot water in the sink after running for several minutes. Black long hairs left in the sink. Breakfast was below expectations. Staff was great!"
Kyle 1-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Winchester, VA

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.