Winchester Hotel Guide - Romantic Hotels in Winchester, Virginia

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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 €443
includes taxes & fees
11 May - 12 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 €120
includes taxes & fees
21 May - 22 May
❤️ Secluded 1940s Romantic Tiny House on the River
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, (360 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 €233
includes taxes & fees
14 May - 15 May
"Walden" Modern Cabin on 54 Riverfront 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 €343
includes taxes & fees
25 May - 26 May
Cozy w Fireplace, Fire Pit, Wifi & Pool Access
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 €233
includes taxes & fees
13 May - 14 May
"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub
Terrace/patio

Sunset Mountain Cabin

Sunset Mountain Cabin
Rileyville
9.8 out of 10, Exceptional, (38 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
11 May - 12 May
Sunset Mountain Cabin
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 €238
includes taxes & fees
17 May - 18 May
"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, (322 reviews)
"Cabin had rustic vibes but is very well taken care of and clean."
United States
Heidi
The price is €243
includes taxes & fees
21 May - 22 May
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
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.
The price is €354
includes taxes & fees
11 May - 12 May
Ridgeview Mountain Cabin
Outdoor spa tub

Overlook Mountain Cabin

Overlook Mountain Cabin
Page County
9.8 out of 10, Exceptional, (166 reviews)
"We loved this little cabin. It’s extremely comfortable and the view is spectacular (and you can enjoy it from the hot tub !) Unless you have a4-wheel drive with good clearance, we recommend taking one of the Jeeps the owner offers up to the house. "
United States
sara r.
The price is €368
includes taxes & fees
11 May - 12 May
Overlook 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

8/10 Good
"Bed was extremely comfortable. Linens were clean and of good quality. Breakfast area was clean, well stocked and attended to. Only one staff member during weekend evening but worked hard to satisfy my issue with non-working remote. Should have been spare or extra remotes at front desk. Hall carpeting needs to be replaced."
Anna 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?
Secret Gardens Carriage House 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 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.