Romantic Hotels & Resorts in Winchester from NZ$243

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Check availability on Winchester Romantic Hotels

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 NZ$877
includes taxes & fees
10 June - 11 June
The Pond Cabin: Hot Tub & Stocked Pond
Smart TV, ping pong, books

Walk to Old Rag | Hot Tub | Mountain Farmhouse

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (21 reviews)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
United States
Mary Margaret R.
The price is NZ$1,016
includes taxes & fees
10 June - 11 June
Walk to Old Rag | Hot Tub | Mountain Farmhouse
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (77 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is NZ$243
includes taxes & fees
29 June - 30 June
❤️ Secluded 1940s Romantic Tiny House on the River
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, (360 reviews)
"Wonderful getaway!"
United States
Samantha T.
The price is NZ$515
includes taxes & fees
25 June - 26 June
"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, (326 reviews)
"Cabin had rustic vibes but is very well taken care of and clean."
United States
Heidi
The price is NZ$515
includes taxes & fees
25 June - 26 June
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
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, (59 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 NZ$684
includes taxes & fees
17 June - 18 June
Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access
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, (107 reviews)
"The house was beyond expectations."
United States
Eddie J.
The price is NZ$688
includes taxes & fees
15 June - 16 June
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Fridge, microwave, oven, stovetop

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, (111 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 NZ$907
includes taxes & fees
15 June - 16 June
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Fireplace, DVD player

Clouds Mountain Cabin

Clouds Mountain Cabin
Rileyville
9.4 out of 10, Exceptional, (16 reviews)
"We had a very quiet nice stay it was nice to have the woods where we could walk the dogs. The drive up was a little difficult even with four wheel drive but definitely worth the view "
United States
Jessica S.
The price is NZ$641
includes taxes & fees
10 June - 11 June
Clouds Mountain Cabin
Outdoor dining

The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.2 out of 10, Wonderful, (71 reviews)
"Quiet setting and friendly owner."
United States
Helen W.
The price is NZ$720
includes taxes & fees
10 June - 11 June
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Breakfast was great and the staff were very nice!"
Madeline 1-night trip
Posted 4 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 Winchester Little Theater 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.