Holiday Homes in Winchester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winchester holiday homes

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (24 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is €190
includes taxes & fees
11 May - 12 May
Mountain View Bungalow in Front Royal

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (40 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is €264
includes taxes & fees
17 May - 18 May
Newly renovated Farm cottage with Mountain views

Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (31 reviews)
"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "
United States
Elissa S.
The price is €293
includes taxes & fees
10 May - 11 May
Mountain home w/ hot tub & sunroom

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 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is €301
includes taxes & fees
10 May - 11 May
Cameron Charmer pristine downtown apt with double master suites

Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
The price is €396
includes taxes & fees
11 May - 12 May
Bluemont home just minutes to wineries, breweries, hiking and more!

Greek Spa on private acreage! Stonefire pizza oven

Greek Spa on private acreage! Stonefire pizza oven
Front Royal
The price is €275
includes taxes & fees
12 May - 13 May
Greek Spa on private acreage! Stonefire pizza oven

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
Comfy Getaway in Strasburg, VA!

4BR Golf Retreat • 3 Courses • Pool Table

4BR Golf Retreat • 3 Courses • Pool Table
Front Royal
4BR Golf Retreat • 3 Courses • Pool Table

Luxury Riverfront Home Getaway with Hot Tub

Luxury Riverfront Home Getaway with Hot Tub
Warren County
Luxury Riverfront Home Getaway with Hot Tub

Virginia Mirror Cabin

Virginia Mirror Cabin
Linden Virginia
The price is €296
includes taxes & fees
12 May - 13 May
Virginia Mirror Cabin

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
9.6 out of 10, Exceptional, (8 reviews)
"Host and everything was very accommodating! Very nice stay"
United States
James G.
The price is €196
includes taxes & fees
9 May - 10 May
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

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, (71 reviews)
"Amazing location and cute design. Would definitely stay here again. "
United States
Ashley
The price is €214
includes taxes & fees
11 May - 12 May
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4

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, (7 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is €313
includes taxes & fees
8 Jun - 9 Jun
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly

Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
Luray
9.8 out of 10, Exceptional, (44 reviews)
"Amazing stay in Luray, VA. House was very clean and up kept "
United States
Shedrick J.
The price is €286
includes taxes & fees
21 May - 22 May
Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly

Sunset Mountain Cabin

Sunset Mountain Cabin
Rileyville
9.8 out of 10, Exceptional, (38 reviews)
"Absolutely enjoyed our time here! So peaceful and beautiful! The host was amazing and very responsive! Loved the hot tub and how very open the space was. Definitely would come back!"
United States
Kim B.
The price is €343
includes taxes & fees
10 May - 11 May
Sunset Mountain Cabin

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (25 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is €340
includes taxes & fees
10 May - 11 May
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Historical home, walkable to many restaurants and shops.

Historical home, walkable to many restaurants and shops.
Luray
9.8 out of 10, Exceptional, (86 reviews)
"Very cute house with lots of charm. Beds were comfortable. Host responded to messages quickly. "
United States
Nicole G.
The price is €224
includes taxes & fees
19 May - 20 May
Historical home, walkable to many restaurants and shops.

Luray farmhouse on the river

Luray farmhouse on the river
Luray
9.4 out of 10, Exceptional, (46 reviews)
"It was a beautiful place, relaxing, great for a group to cook, sit on a porch, next to the deep water of The Shenandoah River. Great beds, kitchen was easy for several people cooking at the same time"
United States
David S.
The price is €336
includes taxes & fees
11 May - 12 May
Luray farmhouse on the river

Stone Cabin on Valley View: Fire Pit + Hot Tub

Stone Cabin on Valley View: Fire Pit + Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is €337
includes taxes & fees
8 Jun - 9 Jun
Stone Cabin on Valley View: Fire Pit + Hot Tub

Modern, family-friendly, nature packed getaway

Modern, family-friendly, nature packed getaway
Berkeley Springs
8.8 out of 10, Excellent, (25 reviews)
"Great secluded place to unwind!"
United States
Dong Y.
The price is €232
includes taxes & fees
10 May - 11 May
Modern, family-friendly, nature packed getaway
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
323
Accommodation
665 Holiday Homes
Lowest Price
€190
Highest Price
€396