Photo by Kelly Godby

Winchester Hotel Guide - Romantic Hotels in Winchester, Virginia

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Check prices for these dates

Our top choices for Winchester romantic hotels

1. 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 €144
includes taxes & fees
7 Dec - 8 Dec
ANS Inn has clean, spacious rooms located on 5 acres with little traffic.

2. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is €90
includes taxes & fees
15 Nov - 16 Nov
❤️ Secluded 1940s Romantic Tiny House on the River

3. Cozy Lakeside Homestead

Cozy Lakeside Homestead
Wardensville
10.0 out of 10, Exceptional, (228 reviews)
"Very clean! Great place to stay!"
United States
Sean M.
The price is €272
includes taxes & fees
16 Nov - 17 Nov
Cozy Lakeside Homestead

4. "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, (391 reviews)
"What a great place they have here."
United States
James W.
The price is €254
includes taxes & fees
15 Nov - 16 Nov
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

5. "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, (378 reviews)
"Amazing location and perfect get away for two"
United States
Heather R.
The price is €247
includes taxes & fees
9 Nov - 10 Nov
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

6. 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, (65 reviews)
"As expected. Very nicely appointed for a cabin in the woods. Did not use the pool or other amenities but they looked nice."
United States
Scott F.
The price is €348
includes taxes & fees
9 Nov - 10 Nov
Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access

7. "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, (345 reviews)
"Balcony, hot tub, and cabin were all very private with great Mountain Views which was exactly what I was looking for"
United States
Elise D.
The price is €250
includes taxes & fees
17 Nov - 18 Nov
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

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

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains
9.0 out of 10, Wonderful, (7 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 €347
includes taxes & fees
12 Nov - 13 Nov
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

9. 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, (332 reviews)
"Very secluded just what we look for."
United States
Tina L.
The price is €766
includes taxes & fees
14 Nov - 15 Nov
Fox Hollow | Romantic Wooded Retreat w/ Fire Pit & Hot Tub

10. "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, (341 reviews)
"We had a great stay at Sundance cabin ! Clean and had alot of nessessities provided . Hot tub was very nice and clean . Can't wait to return and maybe stay in the Walden cabin ."
United States
Joy S.
The price is €296
includes taxes & fees
19 Nov - 20 Nov
"Sundance" Spectacular Views on 54 Acres along Shenandoah River 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.

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 3 hotels and other accommodations in Winchester.

What's the best accommodation for a couple going to Winchester?

Delightful and Serene Hundred Year Old Sweet Space Among the Gardens is a favourite guest house for couples, and features a garden and laundry facilities. Another good option for your romantic getaway 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, 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.