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

Romantic Hotels & Resorts in Winchester from AU$113

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Check availability on Winchester Romantic Hotels

Our top choices for Winchester romantic hotels

Interior

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 AU$232
includes taxes & fees
21 July - 22 July
ANS Inn has clean, spacious rooms located on 5 acres with little traffic.
Cookware/dishes/utensils

The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond
Linden
10.0 out of 10, Exceptional, (35 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 AU$749
includes taxes & fees
21 July - 22 July
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
9.6 out of 10, Exceptional, (80 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is AU$193
includes taxes & fees
3 Aug - 4 Aug
❤️ Secluded 1940s Romantic Tiny House on the River
Smart TV, fireplace

Fox Hollow | Romantic Wooded Retreat w/ Fire Pit & Hot Tub

Fox Hollow | Romantic Wooded Retreat w/ Fire Pit & Hot Tub
Berkeley Springs
9.8 out of 10, Exceptional, (323 reviews)
"Cute little cabin that had everything we needed for a few days. Loved how secluded it was."
United States
Traci E.
The price is AU$525
includes taxes & fees
27 July - 28 July
Fox Hollow | Romantic Wooded Retreat w/ Fire Pit & Hot Tub
Outdoor dining

Cozy Lakeside Homestead

Cozy Lakeside Homestead
Wardensville
10.0 out of 10, Exceptional, (219 reviews)
"Great place! We enjoyed the large family table, cute rooms, hot tub, and the mountain air! "
United States
Megan M.
The price is AU$483
includes taxes & fees
16 Aug - 17 Aug
Cozy Lakeside Homestead
Smart TV, fireplace, DVD player, books

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (109 reviews)
"Wonderful place to stay. Comfotable beds and big enough for a large crowd. The property owners are incredibly kind and responsive. Our family loved our stay. "
United States
Jenn C.
The price is AU$581
includes taxes & fees
2 Aug - 3 Aug
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Coffee/tea maker, fridge, microwave, oven

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Harpers Ferry
9.8 out of 10, Exceptional, (113 reviews)
"The house was as advertised and served as a great location for our retreat! We had a freak plumbing emergency, and the host fixed it within literally an hour. "
United States
Connie V.
The price is AU$842
includes taxes & fees
26 July - 27 July
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
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, (61 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 AU$552
includes taxes & fees
26 July - 27 July
Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access
Exterior

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains
10.0 out of 10, Exceptional, (6 reviews)
"This was a great place to escape to! Very quiet and peaceful but close to some great restaurants and vineyards."
United States
Jill M.
The price is AU$568
includes taxes & fees
21 July - 22 July
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
Outdoor dining

The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (70 reviews)
"Quiet setting and friendly owner."
United States
Helen W.
The price is AU$594
includes taxes & fees
21 July - 22 July
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

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

10/10 Excellent
"Fancy clean and beautiful"
hongjuan 1-night trip
Posted 6 hours ago
Mimslyn Inn Historic Hotels Of America

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, Winchester Little Theater or Bright Box 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?
Secret Gardens Carriage House A Sweet Space Among the Gardens is a favourite guest house for couples, and features a garden and laundry facilities. Other good choices for your romantic getaway 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, 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 Shenandoah Valley Discovery Museum, Winchester Little Theater 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.