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Holiday Homes in Winchester

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Our top choices for Winchester holiday homes

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 NZ$576
includes taxes & fees
15 Nov - 16 Nov
Cameron Charmer pristine downtown apt with double master suites

2. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (51 reviews)
"It was great and beautiful place to staying. Thanks for hospitality"
United States
Onon
The price is NZ$378
includes taxes & fees
22 Nov - 23 Nov
Mountain View Bungalow in Front Royal

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

Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
Front Royal
9.4 out of 10, Exceptional, (3 reviews)
"The gravel road to get to the properly is an adventure. The owner described it perfectly."
United States
Denise A.
The price is NZ$681
includes taxes & fees
15 Nov - 16 Nov
Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6

4. NEW! Greek Spa - Frisbee Golf - Stonefire Pizza

NEW! Greek Spa - Frisbee Golf - Stonefire Pizza
Front Royal
The price is NZ$500
includes taxes & fees
17 Nov - 18 Nov
NEW! Greek Spa - Frisbee Golf - Stonefire Pizza

5. 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, (2 reviews)
"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 NZ$848
includes taxes & fees
30 Nov - 1 Dec
Trailside Retreat | Hot Tub + Sauna, Steps to Buzzard Rock | 4BR, Sleeps 8

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

Cozy 3BR Retreat | Perfect for Families & Groups
Apple Mountain Lake
The price is NZ$557
includes taxes & fees
16 Nov - 17 Nov
Cozy 3BR Retreat | Perfect for Families & Groups

7. 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 NZ$686
includes taxes & fees
15 Nov - 16 Nov
Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6

8. 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 NZ$876
includes taxes & fees
15 Nov - 16 Nov
Pool Table, Fireplace & Deck near Shenandoah Park

9. 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 NZ$791
includes taxes & fees
18 Nov - 19 Nov
Mountain Views w/Hot Tub, 95” TV & Trail Access

10. 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 NZ$1,005
includes taxes & fees
17 Nov - 18 Nov
Sunset Haven - 10 min from Skyline Drive. Hot Tub

11. ⭐️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, (17 reviews)
"Quiet and peaceful retreat to watch the wildlife and stars after hiking in SNP. The dome had everything we needed, and Taylor quickly responded to emails."
United States
Mary W.
The price is NZ$1,228
includes taxes & fees
1 Dec - 2 Dec
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!

12. 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, (14 reviews)
"Wonderful location and property."
United States
Helen F.
The price is NZ$490
includes taxes & fees
14 Nov - 15 Nov
Hidden Creekside retreat near 5 national parks, including Harpers Ferry

13. 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, (25 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
The price is NZ$453
includes taxes & fees
18 Nov - 19 Nov
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

14. Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, Winery

Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, Winery
Harpers Ferry
9.8 out of 10, Exceptional, (16 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 NZ$514
includes taxes & fees
15 Nov - 16 Nov
Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, Winery

15. Schilling House

Schilling House
3.0 star property
Bolivar
The price is NZ$560
includes taxes & fees
23 Nov - 24 Nov
Schilling House

16. Cozy house by the lake.

Cozy house by the lake.
Wardensville
10.0 out of 10, Exceptional, (228 reviews)
"Very clean! Great place to stay!"
United States
Sean M.
The price is NZ$582
includes taxes & fees
30 Nov - 1 Dec
Cozy house by the lake.

17. Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.8 out of 10, Exceptional, (16 reviews)
"We had a great stay "
United States
Lauren O.
The price is NZ$866
includes taxes & fees
18 Nov - 19 Nov
Huckleberry Hills | Hot Tub & Fire Pit & Dogs

18. Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (10 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is NZ$529
includes taxes & fees
16 Nov - 17 Nov
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

19. GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV

GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV
Berkeley Springs
9.8 out of 10, Exceptional, (6 reviews)
"Pet friendly, clean, spacious, great communication, all the amenities we could ask for, this place was perfect for our little family get away! The kids loved the glamping dome and we all loved the hot tub! We will keep this place in mind for sure next time we’re in the area! Thank you Priya and Gauthaman!"
United States
Stephanie H.
The price is NZ$596
includes taxes & fees
18 Nov - 19 Nov
GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV

20. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
Shepherdstown
9.4 out of 10, Exceptional, (6 reviews)
"Very nice place, the lay out is perfect for multiple adults, we stayed for 10 night for work and it was perfect, we will be back for another long stay soon. "
United States
Brandon K.
The price is NZ$642
includes taxes & fees
19 Nov - 20 Nov
Walk to Stores: Home in Historic Shepherdstown!
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

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
189
Accommodation
724 Holiday Homes
Lowest Price
NZ$378
Highest Price
NZ$1,228