Winchester Vacation Home Rentals from CA $300: Search Top Private Vacation Homes for Rent

Winchester Vacation Homes
Virginia
United States of America
Vacation Homes
Expedia.ca

Hotels in Winchester Vacation Rentals in Winchester Flights to Winchester Things to do in Winchester Winchester Car Rentals Winchester Vacation Packages

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
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 vacation homes

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

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a red chair.

A wooden staircase with white railings, leading to a room with a window.

A modern kitchen with wooden cabinets, a dining area with a glass table, and a living room with a sofa and curtains.

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)

9.8/10

Exceptional

(11 reviews)

"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."

Carolyn F.

The price is CA $277

CA $277

CA $470 total

includes taxes & fees

Nov 12 - Nov 13

Cameron Charmer pristine downtown apt with double master suites

A wooden deck with white railings and a covered porch area.

A bedroom with a bed, a dresser, a window, and a mirror.

A single-story house with a covered porch, white railings, and a chimney.

A modern living room with a blue sofa, wooden flooring, a ceiling fan, a TV, and a bookshelf.

2. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal

Front Royal

10.0 out of 10, Exceptional, (47 reviews)

10/10

Exceptional

(47 reviews)

"Perfect place- would stay here again."

HEMANT S.

The price is CA $189

CA $189

CA $300 total

includes taxes & fees

Nov 8 - Nov 9

Mountain View Bungalow in Front Royal

A garden with a wooden swing set and a circular seating area.

A kitchen with wooden flooring, green cabinets, a microwave, a sink, and a window.

A single-story house with a green door, white exterior, and a small front porch.

A bedroom with a large bed, a ceiling fan, a stained glass window, and a view of the outdoors.

3. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views

Strasburg

10.0 out of 10, Exceptional, (56 reviews)

10/10

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!"

Marsha N.

The price is CA $224

CA $224

CA $458 total

includes taxes & fees

Nov 29 - Nov 30

Newly renovated Farm cottage with Mountain views

A lakeside property with a dock, a wooden deck, and a house surrounded by dense greenery.

A spacious living room with a large window, a fireplace, and a bookshelf.

A modern kitchen with white cabinetry, a central island with stools, a ceiling fan, and a view to the outdoors.

A lakeside view with a wooden dock, two chairs, and a house in the background.

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

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"The gravel road to get to the properly is an adventure. The owner described it perfectly."

Denise A.

The price is CA $193

CA $193

CA $549 total

includes taxes & fees

Nov 3 - Nov 4

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

An outdoor dining area with a wooden deck, a table set for four, and a view of the surrounding greenery.

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.

A modern kitchen with a central island, wooden beams, and a bright teal accent wall.

A living room with a blue sofa, wooden beams, a fireplace, and a kitchen in the background.

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

NEW! Greek Spa - Frisbee Golf - Stonefire Pizza

Front Royal

The price is CA $136

CA $136

CA $427 total

includes taxes & fees

Nov 16 - Nov 17

NEW! Greek Spa - Frisbee Golf - Stonefire Pizza

A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

A house with a wooden deck, a porch, and a grassy yard.

A covered porch with white chairs and a table, large windows offering a view of greenery.

Open floor plan perfect for spending time with family and friends.

6. Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom

Front Royal

9.0 out of 10, Wonderful, (32 reviews)

9.0/10

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!"

Mollie S.

The price is CA $239

CA $239

CA $446 total

includes taxes & fees

Nov 3 - Nov 4

Mountain home w/ hot tub & sunroom

A deck with a table set for two, featuring a bottle of champagne, glasses, and a candle.

A wooden cabin with a front door, two windows, and a small porch with steps.

A living room with a TV displaying Netflix content, a remote control, a candle, and a stack of books on a coffee table.

A modern living room with a sectional sofa, a coffee table, and a TV displaying a Netflix interface.

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

Cozy 3BR Retreat | Perfect for Families & Groups

Apple Mountain Lake

The price is CA $256

CA $256

CA $486 total

includes taxes & fees

Nov 4 - Nov 5

Cozy 3BR Retreat | Perfect for Families & Groups

A modern kitchen with a central island, wooden chairs, stainless steel appliances, and pendant lighting.

A kitchen with white cabinets, a microwave, a coffee maker, a sink, and a window.

A circular fire pit with six Adirondack chairs arranged around it on a grassy lawn.

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a sofa and coffee tables.

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 $207

CA $550 total

includes taxes & fees

Nov 11 - Nov 12

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

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)

10/10

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."

Nick G.

The price is CA $193

CA $193

CA $666 total

includes taxes & fees

Nov 11 - Nov 12

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.

A modern kitchen with stainless steel appliances, wooden cabinets, and a stone backsplash.

A living room with a flat-screen TV mounted on a white wall, wooden flooring, and a staircase with wooden railings.

A modern kitchen with wooden cabinets, a stone fireplace, and a bar area with stools.

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)

10/10

Exceptional

(2 reviews)

"Great location. Very quiet neighborhood good for walking"

tom c.

The price is CA $251

CA $251

CA $630 total

includes taxes & fees

Nov 3 - Nov 4

Pool Table, Fireplace & Deck near Shenandoah Park

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)

9.6/10

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!"

Laura D.

The price is CA $454

CA $454

CA $786 total

includes taxes & fees

Nov 18 - Nov 19

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.

A spacious loft with a high ceiling, large windows offering a view of the outdoors, a cozy seating area with a sofa and armchairs, and a flat-screen TV mounted on the wall.

A modern kitchen with wooden accents, a dining area, and a laundry room.

A hot tub on a wooden deck with a view of a house and hills.

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)

10/10

Exceptional

(16 reviews)

"Taylor was great to work with! Nice property and wonderful view ."

Christine H.

The price is CA $440

CA $440

CA $905 total

includes taxes & fees

Nov 3 - Nov 4

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

A deck with a hot tub, wooden chairs, and a table.

Local wineries, breweries, and small-town charm in Front Royal

A modern kitchen with green cabinets, a central island, and a dining area with a table and chairs.

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)

9.0/10

Wonderful

(2 reviews)

"Just as described."

Matt F.

The price is CA $352

CA $352

CA $664 total

includes taxes & fees

Nov 3 - Nov 4

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

A cabin with a deck, outdoor seating, and a fire pit.

A bedroom with a bed, bedside lamps, a window, and a hanging light fixture.

A door with a push button lock labeled 'AUTEL' and a key inserted into the lock.

A modern interior with a staircase, grey sofa, dining table, and a fireplace.

14. A-Frame Soak and Cedar near Skyline Drive and Wineries

A-Frame Soak and Cedar near Skyline Drive and Wineries

Front Royal

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"A very clean house with all the amenities you need for a comfortable and enjoyable vacation."

Arman

The price is CA $329

CA $329

CA $746 total

includes taxes & fees

Nov 2 - Nov 3

A-Frame Soak and Cedar near Skyline Drive and Wineries

A deck with outdoor seating and a lake view.

A spacious hallway with a wooden floor, a stone wall, and a dining area with a table and chairs.

A garden with a stone pathway, surrounded by various plants and trees.

A beach with two empty lounge chairs facing a calm lake, surrounded by a chain-link fence and a dock in the background.

15. Mountain Lake Retreat Harpers Ferry:Hot Tub, Firepit, Fenced Yard, Beach, Winery

Mountain Lake Retreat Harpers Ferry:Hot Tub, Firepit, Fenced Yard, Beach, Winery

Harpers Ferry

9.8 out of 10, Exceptional, (16 reviews)

9.8/10

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!"

Dawn S.

The price is CA $91

CA $91

CA $415 total

includes taxes & fees

Nov 5 - Nov 6

Mountain Lake Retreat Harpers Ferry:Hot Tub, Firepit, Fenced Yard, Beach, Winery

A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

A modern kitchen with granite countertops, stainless steel appliances, and pendant lighting.

A spacious kitchen with granite countertops, stainless steel appliances, and wooden cabinets.

A snowy forest scene with a wooden deck in the foreground.

16. 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)

10/10

Exceptional

(12 reviews)

"Wonderful location and property."

Helen F.

The price is CA $157

CA $157

CA $408 total

includes taxes & fees

Nov 13 - Nov 14

Hidden Creekside retreat near 5 national parks, including Harpers Ferry

A hot tub in a forested area with a rocky ground and trees.

A living room with a blue sofa, a coffee table, and artwork on the wall.

A bedroom with a bed, a ceiling fan, two windows, a nightstand, a lamp, and a painting.

A modern kitchen with white cabinets, stainless steel appliances, and a window with a view.

17. 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)

10/10

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 "

Brett D.

The price is CA $140

CA $140

CA $564 total

includes taxes & fees

Nov 12 - Nov 13

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

A spacious living room with a large window, a wooden coffee table, and a sofa.

A two-story house with a porch, a chimney, and a tree in the front yard.

A living room with a television, a sofa, a coffee table, and a fireplace.

A bathroom with a toilet, sink, and shower curtain.

18. Schilling House

Schilling House

3.0 star property

Bolivar

The price is CA $341

CA $341

CA $435 total

includes taxes & fees

Nov 1 - Nov 2

Schilling House

A hot tub surrounded by a wooden deck, with snow on the ground and trees in the background.

A wooden deck with a rope ladder, a tire, and logs labeled "Blazin' Bundle."

A wooden sauna room with a bench, a window with curtains, and a view of a living area with a sofa and a colorful blanket.

A window with a view of a snowy landscape, a black lantern, and some greenery on the windowsill.

19. Cozy Lakeside Homestead

Cozy Lakeside Homestead

Wardensville

10.0 out of 10, Exceptional, (228 reviews)

10/10

Exceptional

(228 reviews)

"Very clean! Great place to stay!"

Sean M.

The price is CA $314

CA $314

CA $422 total

includes taxes & fees

Nov 3 - Nov 4

Cozy Lakeside Homestead

A hot tub with two glasses of red wine on a wooden tray.

A cozy cabin interior with a TV, fireplace, sofa, and large windows.

A kitchen with a coffee machine, microwave, and storage shelves.

A house with a hot tub, a dome structure, and a small shed with lights.

20. 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)

9.8/10

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!"

Stephanie H.

The price is CA $147

CA $147

CA $481 total

includes taxes & fees

Nov 2 - Nov 3

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

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.

View all properties

Find vacation rentals that suit your style

Cabins

search for cabins

Apartments

search for apartments

Private vacation homes

search for private vacation homes

Cottages

Chalets

Villas

Condos

Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

TRU By Hilton Winchester

10/10 Excellent

"This a very nice place to stay. The breakfast hit the spot. We would stay here again."

Betsy 1-night trip

Posted 4 hours ago

TRU By Hilton Winchester

Ramada by Wyndham Strasburg/Shenandoah Valley

10/10 Excellent

"Nice clean hotel. Breakfast was good."

Marybeth 1-night trip

Posted 8 hours ago

Ramada by Wyndham Strasburg/Shenandoah Valley

Quality Inn Winchester

10/10 Excellent

"Very clean and economical"

MARIA CECILIA 7-night trip

Posted 13 hours ago

Quality Inn Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent

"Very nice place, will return!"

Jonathan 1-night trip

Posted 23 hours ago

Microtel Inn & Suites by Wyndham Winchester

Spark by Hilton Winchester

10/10 Excellent

"Excellent stay! Big king room."

angie 2-night trip

Posted 1 day ago

Spark by Hilton Winchester

Skyland

8/10 Good

"The shower had rather low water pressure and it took a couple tries to get the space heater in the bathroom to work. Other than that, clean comfortable room."

Robert 3-night trip

Posted 2 days ago

Skyland

Days Inn by Wyndham Winchester

10/10 Excellent

"Rooms were dated but very clean. Room was quiet and beds were comfortable. Plentiful hot water for showers."

karen 1-night trip

Posted 2 days ago

Days Inn by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent

"Nice clean stay!"

Pamela 1-night trip

Posted 2 days ago

Travelodge by Wyndham Winchester

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews	217
Accommodation	729 Vacation Homes
Lowest Price	CA $300
Highest Price	CA $905

Explore a world of travel with Expedia

Lodging
Flights
Cars
Other
More ways to book

Gateway Inn
Cheap Hotels in Winchester
Towneplace Suites by Marriott Front Royal
Aparthotels in Prince William County
B&B in Potomac Falls
Berryville Hotels
Hotels with Kitchenettes in Winchester
Apartments in Millwood
Condo Rentals in Stephens City
Luxury Hotels in Gore
Lodges in Riverton
Condo Rentals in Skyland
Hampton Inn Front Royal
Historic Hotels in Stephens City
Hotels near Washington Dulles Intl.
Strasburg Hotels
4 Star Hotels in Winchester
Front Royal Hotels
Ramada by Wyndham Strasburg/Shenandoah Valley
Middletown Hotels
Quality Inn Stephens City
Apartments in Skyland
Pet-Friendly Hotels in Winchester
Motels in Gore
Breathtaking View with an Indoor Pool
Hotels near Bluemont Vineyard
Gainesboro Hotels
Cabin Rentals in Paris
Blue Ridge Motel
Vacation Homes in Luray
Baymont by Wyndham Front Royal Near Shenandoah National Park
Doubletree by Hilton Front Royal Blue Ridge Shadows
Relax Inn Motel
Twi
Cabin Rentals in Northern Virginia
B&B in Boyce
5 Star Hotels in Middletown
Hygge River House • Hot Tub
Old Town Winchester Hotels
Motels in Casanova
Motels in Warrenton
Apartments in Sterling
Villas in Orlean
Cabin Rentals in New Market
Cozy Mountain Retreat with Pickle
Rv Parks in Woodstock
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Hotels with a Pool in Winchester
L'auberge Provencale Inn & Restaurant
Best Western Hotels in Winchester
Cottages in Forestville
Pet-Friendly Hotels in Strasburg
Motels in Winchester
Resorts in Airlie
B&B in Bristow
Spark by Hilton Winchester
Winchester Hotels
Vacation Homes in Casanova
Holiday Inn Express Winchester South
Motels in Northern Virginia
5 Star Hotels in Strasburg
Cheap Hotels in Stephens City
Resorts in Sterling
Apartments in Winchester
Farmstay in Bristow
Farmstay in Woodville
Farmstay in Paeonian Springs
Sean's Bar Cozy Irish Retreat
Linden Hotels
Apartments in Huntly
Secluded River Cabin Getaway (Masten Cabin)
Front Royal Hilltop Cabin w/ Panoramic Views!
Paris Hotels

Flights to Boyce
Flights from Mesa (AZA) to Winchester (WGO)
Flights from El Paso (ELP) to Winchester (WGO)
Flights from Toronto (YYZ) to Winchester (WGO)
Flights from Vancouver (YVR) to Washington (IAD)
Flights from Star Tannery
Flights from Winchester Regional
Flights from Hartford (BDL) to Winchester (WGO)
Flights from Syracuse (SYR) to Winchester (WGO)
Flights from Dallas (DFW) to Winchester (WGO)
Flights to Front Royal
Flights from Fort Lauderdale (FLL) to Winchester (WGO)
Flights from Denver (DEN) to Winchester (WGO)
Flights from Montreal (YUL) to Washington (IAD)
Flights from Calgary (YYC) to Winchester (WGO)
Flights from Washington Dulles Intl.
Flights to Millwood
Flights from Greenville (GSP) to Winchester (WGO)
Flights from New York (LGA) to Winchester (WGO)
Flights to Winchester
Flights to Syria
Flights from Toronto (YYZ) to Washington (IAD)

Rental cars Washington Dulles Intl. airport
Car rental Front Royal
National Car Rental Rental Cars in Winchester

Things to do in Winchester
Things to do in Bluemont

Book Vacation Homes in Winchester on Expedia.com

Winchester Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester vacation homes

1. Cameron Charmer pristine downtown apt with double master suites

2. Mountain View Bungalow in Front Royal

3. Newly renovated Farm cottage with Mountain views

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

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

6. Mountain home w/ hot tub & sunroom

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

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

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

10. Pool Table, Fireplace & Deck near Shenandoah Park

11. Sunset Haven - 10 min from Skyline Drive. Hot Tub

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

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

14. A-Frame Soak and Cedar near Skyline Drive and Wineries

15. Mountain Lake Retreat Harpers Ferry:Hot Tub, Firepit, Fenced Yard, Beach, Winery

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

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

18. Schilling House

19. Cozy Lakeside Homestead

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

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

TRU By Hilton Winchester

Find out more about Winchester

Winchester Vacation Homes information

Explore a world of travel with Expedia