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Check availability on Winchester Romantic Hotels

Tonight
19 Sep - 20 Sep
Tomorrow
20 Sep - 21 Sep
Next weekend
25 Sep - 27 Sep
In two weeks
2 Oct - 4 Oct

Our top choices for Winchester romantic hotels

DVD player, books, video library
3 bedrooms, WiFi (free), bed sheets
Outdoor spa tub
Cookware/dishes/utensils

1. The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond
Linden
United States
Mary S.
AED 926
AED 1,977 total
includes taxes & fees
29 Sep - 30 Sep
The Pond Cabin: Hot Tub & Stocked Pond
Terrace/patio
Coffee/tea maker, fridge, microwave, oven
1 bedroom, iron/ironing board, WiFi, bed sheets
Coffee/tea maker, fridge, microwave, oven

2. Large Glamper w/ Hot Tub and full bathroom-sleep 6

Large Glamper w/ Hot Tub and full bathroom-sleep 6
Capon Bridge
United States
Mary
AED 413
AED 889 total
includes taxes & fees
21 Sep - 22 Sep
Large Glamper w/ Hot Tub and full bathroom-sleep 6
Exterior
Property grounds
Dining
WiFi (free), bed sheets

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
United States
Joseph
AED 152
AED 392 total
includes taxes & fees
1 Oct - 2 Oct
❤️ Secluded 1940s Romantic Tiny House on the River
Dining
Property grounds
Exterior
Coffee/tea maker, fridge, microwave, oven

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

Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access
The Woods
United States
Eric S.
AED 611
AED 1,434 total
includes taxes & fees
21 Sep - 22 Sep
Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access
Pool
Exterior
Smart TV, fireplace, stereo
Indoor spa tub

5. "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
United States
Dave A.
AED 578
AED 1,022 total
includes taxes & fees
24 Sep - 25 Sep
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Property grounds
Coffee/tea maker, fridge, microwave, oven
Smart TV, fireplace, books, stereo
Exterior

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

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Rileyville
United States
Elise D.
AED 544
AED 970 total
includes taxes & fees
22 Sep - 23 Sep
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Outdoor spa tub
Property grounds
Smart TV, fireplace, stereo
Smart TV, fireplace, stereo

7. "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
United States
Scott C.
AED 544
AED 940 total
includes taxes & fees
23 Sep - 24 Sep
"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub
Outdoor spa tub
Smart TV, fireplace, stereo
Exterior
Smart TV, fireplace, stereo

8. "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
United States
Bernard L.
AED 578
AED 1,022 total
includes taxes & fees
24 Sep - 25 Sep
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Exterior
Property grounds
Dining
Terrace/patio

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

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains
United States
Jill M.
AED 909
AED 1,480 total
includes taxes & fees
24 Sep - 25 Sep
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
View all properties

Top Winchester Hotel Reviews

Skyland

Skyland

10/10 Excellent
"Wonderful location and amenities Great view 👌"
SARI 1-night trip
Posted 6 hours ago
Skyland
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"Great stay."
Allen 3-night trip
Posted 13 hours ago
Country Inn & Suites by Radisson, Winchester, VA
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Loved the room set up"
Tracy 1-night trip
Posted 22 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 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 3 hotels and other accommodations in Winchester.
What's the best hotel for a couple visiting Winchester?
Delightful and Serene Hundred Year Old Sweet Space Among the Gardens is a favorite guesthouse for couples, and features a garden and laundry facilities. Another good option for a romantic stay 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, 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.