A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winchester vacation homes

A two-story house with a front porch, a mailbox, and a number plate.

1. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.8 out of 10, Exceptional, (11 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
United States
Carolyn F.
The price is CA $277
CA $495 total
includes taxes & fees
Oct 26 - Oct 27
Cameron Charmer pristine downtown apt with double master suites
A wooden deck with white railings and a covered porch area.

2. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (46 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is CA $189
CA $313 total
includes taxes & fees
Oct 29 - Oct 30
Mountain View Bungalow in Front Royal
A garden with a wooden swing set and a circular seating area.

3. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (56 reviews)
"We enjoyed our stay here. The property was lovely and the house was nicely stocked and decorated. We will definitely stay again when in the area!"
United States
Marsha N.
The price is CA $224
CA $459 total
includes taxes & fees
Oct 28 - Oct 29
Newly renovated Farm cottage with Mountain views
A lakeside property with a dock, a wooden deck, and a house surrounded by dense greenery.

4. Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6

Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
Front Royal
The price is CA $194
CA $554 total
includes taxes & fees
Oct 29 - Oct 30
Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
A modern kitchen with white cabinets, a central island with stools, a dining area with a wooden table and chairs, and a large window with blinds.

5. Greek Spa - Frisbee Golf - Stone fire Pizza Oven

Greek Spa - Frisbee Golf - Stone fire Pizza Oven
Front Royal
The price is CA $141
CA $448 total
includes taxes & fees
Nov 16 - Nov 17
Greek Spa - Frisbee Golf - Stone fire Pizza Oven
A fire feature with a glass enclosure, a wicker sofa with cushions, and a wooden deck with string lights.

6. Cozy 3BR Retreat | Perfect for Families & Groups

Cozy 3BR Retreat | Perfect for Families & Groups
Apple Mountain Lake
The price is CA $217
CA $424 total
includes taxes & fees
Oct 26 - Oct 27
Cozy 3BR Retreat | Perfect for Families & Groups
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

7. Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (32 reviews)
"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 CA $225
CA $429 total
includes taxes & fees
Nov 3 - Nov 4
Mountain home w/ hot tub & sunroom
A compact kitchen with white cabinets, a black refrigerator, and a dining area with a round table and chairs.

8. Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6

Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6
Front Royal
The price is CA $207
CA $570 total
includes taxes & fees
Oct 26 - Oct 27
Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6
Living area

9. Trailside Retreat | Hot Tub + Sauna, Steps to Buzzard Rock | 4BR, Sleeps 8

Trailside Retreat | Hot Tub + Sauna, Steps to Buzzard Rock | 4BR, Sleeps 8
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Matt is an awesome host! This place is perfect for 2 families traveling together (fully furnished upstairs & downstairs), or 1 family wanting extra space. The hot tub is an absolute must in the fall/winter for maximum relaxation. LOVED the fire table & Blackstone grill. Very nice remodeling & appliances. Cool arcade console! Could not manage to get the fireplaces to work however."
United States
Nick G.
The price is CA $208
CA $709 total
includes taxes & fees
Nov 4 - Nov 5
Trailside Retreat | Hot Tub + Sauna, Steps to Buzzard Rock | 4BR, Sleeps 8
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

10. Pool Table, Fireplace & Deck near Shenandoah Park

Pool Table, Fireplace & Deck near Shenandoah Park
Front Royal
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Very quiet neighborhood good for walking"
United States
tom c.
The price is CA $300
CA $726 total
includes taxes & fees
Oct 28 - Oct 29
Pool Table, Fireplace & Deck near Shenandoah Park
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11. Sunset Haven - 10 min from Skyline Drive. Hot Tub

Sunset Haven - 10 min from Skyline Drive. Hot Tub
Front Royal
9.6 out of 10, Exceptional, (8 reviews)
"Really enjoyed our stay. The house was lovely with amazing views. The bar and game room were fun. Lots of detail and thought were put into making this house feel like home. We will definitely be back!"
United States
Laura D.
The price is CA $410
CA $770 total
includes taxes & fees
Oct 27 - Oct 28
Sunset Haven - 10 min from Skyline Drive. Hot Tub
A spacious loft bedroom with a large window, a cozy seating area, and a flat-screen TV.

12. ⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!

⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
Front Royal
10.0 out of 10, Exceptional, (16 reviews)
"Taylor was great to work with! Nice property and wonderful view ."
United States
Christine H.
The price is CA $441
CA $953 total
includes taxes & fees
Nov 4 - Nov 5
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
A deck with a hot tub, wooden chairs, and a table.

13. Mountain Views w/Hot Tub, 95” TV & Trail Access

Mountain Views w/Hot Tub, 95” TV & Trail Access
Shenandoah Farms
9.0 out of 10, Wonderful, (2 reviews)
"Just as described."
United States
Matt F.
The price is CA $363
CA $658 total
includes taxes & fees
Oct 28 - Oct 29
Mountain Views w/Hot Tub, 95” TV & Trail Access
A house with a well-lit entrance, a small garden, and a gravel driveway.

14. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (24 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
The price is CA $120
CA $362 total
includes taxes & fees
Oct 26 - Oct 27
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
A deck with outdoor seating and a lake view.

15. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
10.0 out of 10, Exceptional, (14 reviews)
"We had a lovely stay and it was so nice for our dog as well. The Mountain Lake Cub had a doggy beach day on Saturday morning and it was a super fun experience. The host was friendly and responsive!"
United States
Dawn S.
The price is CA $49
CA $368 total
includes taxes & fees
Oct 26 - Oct 27
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A hot tub in a forested area with a rocky ground and trees.

16. The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (6 reviews)
"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "
United States
Brett D.
The price is CA $140
CA $519 total
includes taxes & fees
Oct 29 - Oct 30
The Blue Jay | New House in the Woods w/ Hot Tub
A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

17. Hidden Creekside retreat near 5 national parks, including Harpers Ferry

Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Martinsburg
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful location and property."
United States
Helen F.
The price is CA $175
CA $432 total
includes taxes & fees
Nov 13 - Nov 14
Hidden Creekside retreat near 5 national parks, including Harpers Ferry
A kitchen with white cabinets, a black refrigerator, a wooden table, and a ceiling fan.

18. Schilling House

Schilling House
3.0 star property
Bolivar
The price is CA $326
CA $419 total
includes taxes & fees
Nov 24 - Nov 25
Schilling House
A hot tub surrounded by a wooden deck, with snow on the ground and trees in the background.

19. Cozy Lakeside Homestead

Cozy Lakeside Homestead
Wardensville
10.0 out of 10, Exceptional, (227 reviews)
"Very clean! Great place to stay!"
United States
Sean M.
The price is CA $315
CA $444 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Lakeside Homestead
A small, single-story wooden cabin with a white-framed door and a small porch.

20. Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Rixeyville
9.8 out of 10, Exceptional, (16 reviews)
"Very comfortable and clean space. Plenty of room for 1 or 2 people. Check in and out instructions were very detailed. Price was very affordable compared to the nicer hotels in town who were charging $200 to $300 a night. Kind of out in the country but its easy to get to and from town, pretty straight stretch. I was only there in the evenings and everything was very quiet and peaceful."
United States
emily
The price is CA $125
CA $314 total
includes taxes & fees
Oct 26 - Oct 27
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
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

Skyland

Skyland

8/10 Good
"Servers had to many tables, resulting in very slow service. Not any fault with servers, they just had to many tables."
James 2-night trip
Posted 5 hours ago
Skyland

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
473
Accommodation
729 Vacation Homes
Lowest Price
CA $313
Highest Price
CA $953

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