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12 Dec - 14 Dec
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19 Dec - 21 Dec
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2 Jan - 4 Jan
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30 Jan - 1 Feb

Vacation Homes in Winchester

Smart TV, foosball
3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!

3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!

Stephens City
9.2 out of 10, Wonderful, (7)
"Had a great stay at this property for a girls weekend. Nearby to cute shops, a nice winery, grocery stores and restaurants. Nice amenities with games, entertainment systems, outdoor space, and in a great neighborhood too. Lots of space for families or friend reunions. Will rent again here when staying in the area. "
United States
Maureen W.
The price is SAR 409
SAR 1,094 total
includes taxes & fees
4 Dec - 5 Dec
3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!
Fridge, microwave, oven, stovetop
Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal

Front Royal
10.0 out of 10, Exceptional, (11)
"Excelente propiedad "
Mexico
Miguel
The price is SAR 506
SAR 835 total
includes taxes & fees
11 Dec - 12 Dec
Mountain View Bungalow in Front Royal
Terrace/patio
Historic Bluemont Village Home

Historic Bluemont Village Home

Bluemont
10.0 out of 10, Exceptional, (37)
"No need to look any further! Beautiful, clean,historic home in a perfect location. Close to wineries, breweries, Shenandoah River, hiking and only 45 minutes from DC. The host was very accommodating and friendly as well. We would highly recommend this home for you and your family. "
United States
Brian and Allison W.
The price is SAR 591
SAR 1,606 total
includes taxes & fees
3 Dec - 4 Dec
Historic Bluemont Village Home
Microwave, oven, stovetop, dishwasher
Welcome to the Ladybug Retreat!

Welcome to the Ladybug Retreat!

Boyce
10.0 out of 10, Exceptional, (1)
"This home is lovely and the host has thought of everything. We will definitely stay here again. "
United States
Catherine A.
The price is SAR 657
SAR 1,531 total
includes taxes & fees
15 Dec - 16 Dec
Welcome to the Ladybug Retreat!
Outdoor dining
Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views

Strasburg
10.0 out of 10, Exceptional, (38)
"Fantastic property. Clean, well-stocked, and peaceful. "
United States
Robert M.
The price is SAR 600
SAR 1,200 total
includes taxes & fees
8 Dec - 9 Dec
Newly renovated Farm cottage with Mountain views
Fridge, microwave, oven, stovetop
Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites

Winchester
9.4 out of 10, Exceptional, (6)
"Nice house in a good central location. "
United States
Mitchell V.
The price is SAR 743
SAR 1,310 total
includes taxes & fees
3 Dec - 4 Dec
Cameron Charmer pristine downtown apt with double master suites
Fridge, microwave, oven, stovetop
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

Linden
10.0 out of 10, Exceptional, (20)
"View was great, was pretty isolated from other houses in the area, and cute decor. Very comfortable stay. "
United States
Andrew G.
The price is SAR 550
SAR 1,282 total
includes taxes & fees
9 Dec - 10 Dec
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Exterior
The Apple Mountain House

The Apple Mountain House

Front Royal
9.6 out of 10, Exceptional, (8)
"Amazing place to relax."
United States
Edna K.
The price is SAR 440
SAR 1,395 total
includes taxes & fees
3 Dec - 4 Dec
The Apple Mountain House
Fridge, microwave, oven, stovetop
Big Sunny Family House

Big Sunny Family House

Front Royal
10.0 out of 10, Exceptional, (40)
"Wonderful house and town! Loved every minute of our trip! "
United States
MaryAnn G.
The price is SAR 642
SAR 1,628 total
includes taxes & fees
3 Dec - 4 Dec
Big Sunny Family House
Terrace/patio
Luxury Riverfront Home Getaway with Hot Tub

Luxury Riverfront Home Getaway with Hot Tub

2.0 star property
Warren County
The price is SAR 818
SAR 1,781 total
includes taxes & fees
15 Dec - 16 Dec
Luxury Riverfront Home Getaway with Hot Tub
Interior
Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

Front Royal
8.8 out of 10, Excellent, (29)
"The cottage was amazing!! The hot tub was great and check in was super easy :) Internet and phone service were very good, and the cottage was stocked with all the kitchen utensils and linens we could have needed!"
United States
Mollie S.
The price is SAR 635
SAR 1,143 total
includes taxes & fees
9 Dec - 10 Dec
Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!
Microwave, oven, stovetop, dishwasher
Front royal majestic paradise

Front royal majestic paradise

Front Royal
The price is SAR 4,502
SAR 5,822 total
includes taxes & fees
3 Dec - 4 Dec
Front royal majestic paradise
TV, fireplace
Jacuzzi • Gym • Deck + Near VA Wineries

Jacuzzi • Gym • Deck + Near VA Wineries

2.0 star property
Warren County
Jacuzzi • Gym • Deck + Near VA Wineries
Terrace/patio
Pirate's Cove River Front Oasis, Group Adventure

Pirate's Cove River Front Oasis, Group Adventure

Warren County
10.0 out of 10, Exceptional, (4)
"The entire property was spectacular!!! We had a fantastic time and Aaron and Melissa were wonderful with communication. We didn't want to leave Pirates Cove and we can't wait to stay again!"
United States
Melany S.
The price is SAR 2,926
SAR 4,895 total
includes taxes & fees
14 Dec - 15 Dec
Pirate's Cove River Front Oasis, Group Adventure
Fridge, microwave, oven, stovetop
Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA

Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA

Linden
10.0 out of 10, Exceptional, (2)
"This place was very nice and well equipped with everything that you would need. It was very clean, quiet and had plenty of space. This is a great place to stay if you're in the area. "
United States
Michael C.
The price is SAR 1,073
SAR 2,061 total
includes taxes & fees
14 Dec - 15 Dec
Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA
Fridge, microwave, oven, stovetop
Peaceful Retreat on Creekside

Peaceful Retreat on Creekside

Edinburg
9.6 out of 10, Exceptional, (14)
"Amazing location that was perfect for a weekend getaway! The creek was so peaceful and water views from the deck were amazing! "
United States
Richard D.
The price is SAR 351
SAR 780 total
includes taxes & fees
1 Jan - 2 January 2026
Peaceful Retreat on Creekside
Outdoor spa tub
The Blue Pearl by Zen Living

The Blue Pearl by Zen Living

Luray
10.0 out of 10, Exceptional, (11)
"The Blue Pearl is a wonderful spot in Luray! It is in a wonderful location just minutes away from Luray Caverns, Shenandoah National Park, wineries, and the Main Street for cafes and restaurants. The home was exactly as pictured, clean, well equipped for all of our needs, and welcoming to our fur-baby. Jason was incredibly kind and communicative. This home will be our stay-of-choice whenever we return to the area! "
United States
Mary S.
The price is SAR 366
SAR 1,076 total
includes taxes & fees
3 Dec - 4 Dec
The Blue Pearl by Zen Living
Property grounds
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Harpers Ferry
9.6 out of 10, Exceptional, (101)
"The house was beyond expectations."
United States
Eddie J.
The price is SAR 417
SAR 1,462 total
includes taxes & fees
3 Dec - 4 Dec
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Smart TV, Hulu, streaming services
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4

Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4

Luray
10.0 out of 10, Exceptional, (63)
"Ideal location "
United States
Jeremiah B.
The price is SAR 338
SAR 861 total
includes taxes & fees
8 Dec - 9 Dec
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4
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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Wonderful stay - staff was friendly and knowledgeable about the goings on in town for the holidays which helped plan our trip can’t wait to go back"
Jeanette 1-night trip
Posted 17 hours ago
The George Washington Hotel, A Wyndham Grand Hotel