Winchester Hotel Guide - Romantic Hotels in Winchester, Virginia

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Check availability on Winchester Romantic Hotels

Tonight
25 Mar - 26 Mar
Tomorrow
26 Mar - 27 Mar
This weekend
27 Mar - 29 Mar
Next weekend
3 Apr - 5 Apr

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)
"It was the perfect home away from home in a place that allowed our little family to take a breath of nature and just be. Close enough to many fun adventures. The amenities provided on the property also kept us very busy!"
United States
Brena H.
The price is €437
includes taxes & fees
26 Mar - 27 Mar
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, (72 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is €118
includes taxes & fees
6 Apr - 7 Apr
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

Private Romantic Cabin Retreat w/ Hot Tub

Private Romantic Cabin Retreat w/ Hot Tub
Berkeley Springs
9.8 out of 10, Exceptional, (305 reviews)
"This was so a wonderful cabin with so much privacy!Will be coming back. "
United States
Jamie S.
The price is €325
includes taxes & fees
26 Mar - 27 Mar
Private Romantic Cabin Retreat w/ Hot Tub
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, (358 reviews)
"Great place!"
United States
Donald C.
The price is €229
includes taxes & fees
26 Mar - 27 Mar
"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, (348 reviews)
"Everything was perfect for our stay. "
United States
Debbie O.
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
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, (318 reviews)
"Cabin had rustic vibes but is very well taken care of and clean."
United States
Heidi
The price is €229
includes taxes & fees
26 Mar - 27 Mar
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
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, (324 reviews)
"Incredible views!!"
United States
anthony c.
The price is €242
includes taxes & fees
26 Mar - 27 Mar
"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub
Dining

Cozy w Fireplace, Fire Pit, Wifi & Pool Access

Cozy w Fireplace, Fire Pit, Wifi & Pool Access
The Woods
9.8 out of 10, Exceptional, (59 reviews)
"The host was very responsive whenever I texted about questions and doing a check in the day of and a check in the day of checkout. The house was beautiful and well maintained and any minor issues I had were quickly addressed. I would definitely stay at this house in the future. "
United States
Paula M.
The price is €344
includes taxes & fees
5 Apr - 6 Apr
Cozy w Fireplace, Fire Pit, Wifi & Pool Access
Terrace/patio

Sunset Mountain Cabin

Sunset Mountain Cabin
Rileyville
9.8 out of 10, Exceptional, (37 reviews)
"Absolutely enjoyed our time here! So peaceful and beautiful! The host was amazing and very responsive! Loved the hot tub and how very open the space was. Definitely would come back!"
United States
Kim B.
The price is €342
includes taxes & fees
26 Mar - 27 Mar
Sunset Mountain Cabin
Fireplace, DVD player

Ridgeview Mountain Cabin

Ridgeview Mountain Cabin
Rileyville
9.4 out of 10, Exceptional, (43 reviews)
"We had a great stay at this cabin! Host was responsive and gave many ideas of what to do. The cabin was cozy and it was a perfect stay! A must see is the caverns about 20-30 min away. We drove a Subaru Outback suv and had no problem with the road going up to the cabin, if it snows it can be slippery and icy going down, drive very slow. Overall 5 star stay! Thanks "
United States
Stephanie C.
Ridgeview Mountain Cabin
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"All was good, except on this stay the breakfast was lacking in quality, availability, and assortment. "
PAUL F 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Winchester

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 4 hotels and other accommodations in Winchester.
What's the best accommodation for a couple going to Winchester?
Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed is a favourite guest house for couples, and features a garden and laundry facilities. Other good choices for your romantic getaway include Secret Gardens Carriage House 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 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.