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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Winchester vacation homes

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)
"My husband and I stayed here for a short weekend vacation in Shenandoah. It’s a very cute, clean, and cozy home. We loved the front porch and the view. We had a small mishap with our combination when we first arrived, but the host was very quick to respond and it was resolved in only a few minutes. My husband and I would both stay here again! "
United States
sara h.
The price is AED 496
AED 813 total
includes taxes & fees
10 Dec - 11 Dec
Mountain View Bungalow in Front Royal
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 AED 474
AED 1,163 total
includes taxes & fees
17 Dec - 18 Dec
3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!
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 AED 588
AED 1,187 total
includes taxes & fees
10 Dec - 11 Dec
Newly renovated Farm cottage with Mountain views
Terrace/patio
Historic Bluemont Village Home

Historic Bluemont Village Home

Bluemont
10.0 out of 10, Exceptional, (38)
"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.
Historic Bluemont Village Home
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 AED 727
AED 1,282 total
includes taxes & fees
10 Dec - 11 Dec
Cameron Charmer pristine downtown apt with double master suites
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 AED 643
AED 1,487 total
includes taxes & fees
10 Dec - 11 Dec
Welcome to the Ladybug Retreat!
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 AED 539
AED 1,255 total
includes taxes & fees
10 Dec - 11 Dec
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
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 AED 801
AED 1,731 total
includes taxes & fees
10 Dec - 11 Dec
Luxury Riverfront Home Getaway with Hot Tub
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 AED 638
AED 1,609 total
includes taxes & fees
15 Dec - 16 Dec
Big Sunny Family House
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 AED 622
AED 1,111 total
includes taxes & fees
10 Dec - 11 Dec
Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!
Exterior
The Apple Mountain House

The Apple Mountain House

Front Royal
9.6 out of 10, Exceptional, (9)
"Amazing place to relax."
United States
Edna K.
The price is AED 771
AED 1,782 total
includes taxes & fees
10 Dec - 11 Dec
The Apple Mountain House
Microwave, oven, stovetop, dishwasher
Front royal majestic paradise

Front royal majestic paradise

Front Royal
The price is AED 4,407
AED 5,663 total
includes taxes & fees
10 Dec - 11 Dec
Front royal majestic paradise
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, (3)
"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 AED 1,050
AED 1,993 total
includes taxes & fees
15 Dec - 16 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, (15)
"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 AED 343
AED 764 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 AED 359
AED 1,049 total
includes taxes & fees
10 Dec - 11 Dec
The Blue Pearl by Zen Living
Property grounds
Modern, family-friendly, nature packed getaway

Modern, family-friendly, nature packed getaway

Berkeley Springs
9.2 out of 10, Wonderful, (19)
"Great house! We loved the fire pit outside and the beautiful interior. Host was very responsive and helpful! Would def stay here again. "
United States
Erika R.
The price is AED 459
AED 994 total
includes taxes & fees
10 Dec - 11 Dec
Modern, family-friendly, nature packed getaway
Exterior
Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park

Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park

2.0 star property
Luray
10.0 out of 10, Exceptional, (12)
"Great stay- only one night for a friends wedding in Shenandoah. Nice place to stay, no issues! "
United States
Jacquelin S.
The price is AED 533
AED 1,038 total
includes taxes & fees
10 Dec - 11 Dec
Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park
Terrace/patio
Wooded Nest, Cozy 3BR Chalet Near Spas & Hiking

Wooded Nest, Cozy 3BR Chalet Near Spas & Hiking

Berkeley Springs
10.0 out of 10, Exceptional, (2)
"We had a blast! Great place, stocked with everything you need, hot tub was perfect, safe for small kids and close to town! "
United States
Nicole W.
The price is AED 410
AED 1,357 total
includes taxes & fees
11 Dec - 12 Dec
Wooded Nest, Cozy 3BR Chalet Near Spas & Hiking
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, (64)
"Ideal location "
United States
Jeremiah B.
The price is AED 331
AED 843 total
includes taxes & fees
15 Dec - 16 Dec
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4
TV
Historic Queen Anne Family Home w Modern Comforts

Historic Queen Anne Family Home w Modern Comforts

Harpers Ferry
10.0 out of 10, Exceptional, (3)
"The location was great and the host was very east to communicate with."
United States
Liz B.
The price is AED 585
AED 1,388 total
includes taxes & fees
10 Dec - 11 Dec
Historic Queen Anne Family Home w Modern Comforts
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
"Great hotel!"
CHARLES 1-night trip
Posted 2 days ago
The George Washington Hotel, A Wyndham Grand Hotel