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Check availability on Winchester Romantic Hotels

Our top choices for Winchester romantic hotels

Cookware/dishes/utensils

The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond
Linden
10.0 out of 10, Exceptional, (34 reviews)
"We always love staying here. We have stayed at The Pond Cabin multiple times and will continue doing so as long as it is available!"
United States
Mary S.
The price is AED 878
AED 1,892 total
includes taxes & fees
21 May - 22 May
The Pond Cabin: Hot Tub & Stocked Pond
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (74 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is AED 238
AED 488 total
includes taxes & fees
1 Jun - 2 Jun
❤️ Secluded 1940s Romantic Tiny House on the River
Outdoor spa tub

"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub

"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub
Rileyville
10.0 out of 10, Exceptional, (327 reviews)
"Incredible views!!"
United States
anthony c.
The price is AED 514
AED 927 total
includes taxes & fees
21 May - 22 May
"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub
Property grounds

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Rileyville
9.8 out of 10, Exceptional, (324 reviews)
"Cabin had rustic vibes but is very well taken care of and clean."
United States
Heidi
The price is AED 546
AED 973 total
includes taxes & fees
25 May - 26 May
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Outdoor spa tub

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Rileyville
10.0 out of 10, Exceptional, (361 reviews)
"It was exactly what we needed, out of the way and in nature, but close to beautiful attractions and grocery stores "
United States
Aaron A.
The price is AED 546
AED 973 total
includes taxes & fees
25 May - 26 May
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Pool

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Rileyville
10.0 out of 10, Exceptional, (357 reviews)
"Wonderful getaway!"
United States
Samantha T.
The price is AED 578
AED 1,005 total
includes taxes & fees
25 May - 26 May
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Dining

Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access

Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access
The Woods
9.8 out of 10, Exceptional, (59 reviews)
"The cabin was cozy & clean. Kitchen had all the cooking tools that was needed during my stay. It was a perfect spot for my spouse and I while visiting family in the area. "
United States
Eric S.
The price is AED 611
AED 1,476 total
includes taxes & fees
25 May - 26 May
Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access
Exterior

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Harpers Ferry
10.0 out of 10, Exceptional, (160 reviews)
"Had a great stay at Jay's Spy House. Super location and nicely modernized house in the very heart of Harper's Ferry historic district. Jay was very attentive to anything we needed, which turned out to be very little, since everything was provided. Definitely recommend at stay here if visiting HF. "
United States
Bob S.
The price is AED 698
AED 1,473 total
includes taxes & fees
21 May - 22 May
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Outdoor dining

Cozy Lakeside Homestead

Cozy Lakeside Homestead
Wardensville
10.0 out of 10, Exceptional, (213 reviews)
"Paula was very welcoming and told us everything we needed to know! We had a wonderful and relaxing weekend."
United States
Stephanie H.
The price is AED 826
AED 1,133 total
includes taxes & fees
2 Jun - 3 Jun
Cozy Lakeside Homestead
Outdoor dining

The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (69 reviews)
"Quiet setting and friendly owner."
United States
Helen W.
The price is AED 1,194
AED 1,499 total
includes taxes & fees
21 May - 22 May
The Van Gogh Room in Villa
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

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

10/10 Excellent
"This was the second time I stayed here. Reasonably priced and clean. I feel safe there. Parking is right in front of the entrance. Yes, it’s right off the highway and can be slightly noisy, but that doesn’t bother me. "
Leah 3-night trip
Posted 11 hours ago
Hampton Inn Winchester N/Conference Center, VA

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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 4 hotels and other accommodations in Winchester.
What's the best hotel for a couple visiting Winchester?
Secret Gardens Carriage House is a favorite guesthouse for couples, and features a garden and laundry facilities. Other good choices for a romantic stay include Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed 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, 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.