Search Winchester Cottage Rentals from CA $227

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Winchester cottages

Exterior

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is CA $234
CA $340 total
includes taxes & fees
Jul 20 - Jul 21
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Terrace/patio

Apple Mountain House | Hot Tub | Game Room

Apple Mountain House | Hot Tub | Game Room
Front Royal
9.6 out of 10, Exceptional, (14 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is CA $316
CA $812 total
includes taxes & fees
Jun 23 - Jun 24
Apple Mountain House | Hot Tub | Game Room
Terrace/patio

All-Inclusive 4BR | Mountain Views | Hot Tub

All-Inclusive 4BR | Mountain Views | Hot Tub
Front Royal
The price is CA $354
CA $857 total
includes taxes & fees
Jul 15 - Jul 16
All-Inclusive 4BR | Mountain Views | Hot Tub
Outdoor spa tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (14 reviews)
"Excellent place to stay. Shelly is an excellent host. Nice location "
United States
Lisa H.
The price is CA $414
CA $610 total
includes taxes & fees
Jun 28 - Jun 29
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Terrace/patio

The VUE | Mountaintop 4BR | Hot Tub & Views

The VUE | Mountaintop 4BR | Hot Tub & Views
Front Royal
10.0 out of 10, Exceptional, (23 reviews)
"We loved this home Met our expectations and then some ! We will definitely be back "
United States
Shay B.
The price is CA $478
CA $927 total
includes taxes & fees
Jul 16 - Jul 17
The VUE | Mountaintop 4BR | Hot Tub & Views
Exterior

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Luray
9.8 out of 10, Exceptional, (98 reviews)
"Highly recommend! Great location."
United States
Daren E.
The price is CA $215
CA $452 total
includes taxes & fees
Jun 22 - Jun 23
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Exterior

Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (23 reviews)
"The house had wonderful spaces to use for our weekend getaway!"
United States
Jessame P.
The price is CA $142
CA $516 total
includes taxes & fees
Jul 6 - Jul 7
Lake View Retreat - Cottage Near a Peaceful Lake!
Outdoor spa tub

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (23 reviews)
"Great view, very secluded"
United States
Matt s.
Cottage w/ Hot Tub and 100-Mile Valley Views!
Exterior

Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (26 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is CA $146
CA $493 total
includes taxes & fees
Jun 29 - Jun 30
Woodsy Retreat with a Hot Tub and Seasonal Views!
Exterior

Peaceful Waterfall House -- 2 bedroom hidden treasure

Peaceful Waterfall House -- 2 bedroom hidden treasure
Berkeley Springs
9.8 out of 10, Exceptional, (13 reviews)
"House was great, though a little cold for the winter. Perfect place to get away! "
United States
Krystal A.
The price is CA $316
CA $490 total
includes taxes & fees
Jul 14 - Jul 15
Peaceful Waterfall House -- 2 bedroom hidden treasure
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (27 reviews)
"Great house and location! "
United States
Johanna S.
The price is CA $309
CA $529 total
includes taxes & fees
Jul 2 - Jul 3
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Outdoor dining

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (26 reviews)
"The host was prompt with answering any inquiries. The house was well stocked. Great area to visit."
United States
Ellen B.
The price is CA $337
CA $903 total
includes taxes & fees
Jun 24 - Jun 25
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Exterior

18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (61 reviews)
"Loved out stay! "
United States
Emilee
The price is CA $389
CA $565 total
includes taxes & fees
Jul 2 - Jul 3
18th Century Stone Cottage minutes from historic Middleburg
1 bedroom, WiFi, bed sheets

The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (48 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is CA $175
CA $227 total
includes taxes & fees
Jul 8 - Jul 9
The Carriage House at Carrot Top Cottage
Terrace/patio

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
10.0 out of 10, Exceptional, (21 reviews)
"GREAT stay…loved the location, the hot tub, the amenities, and the host."
United States
Domenic E.
The price is CA $354
CA $608 total
includes taxes & fees
Jul 6 - Jul 7
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

Royal Heritage Home @ Historic Leesburg
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (40 reviews)
"Awesome spot, truly walking distance to all the cool little downtown stuff. Host was kind and there wasn't almost any check out procedure! "
United States
Charles K.
Royal Heritage Home @ Historic Leesburg
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

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"An “Excellent” rating is True for “TRU”. Plenty of parking space, lively staff, vibrant interiors and decor, work space and game options, adequate luggage karts, clean rooms, and hot breakfast. Everything that needs to be in place was in place for a comfortable and peaceful stay. "
Krishna 1-night trip
Posted 1 hour ago
TRU By Hilton Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
448
Accommodation
190 Cottages
Lowest Price
CA $227
Highest Price
CA $927

Frequently asked questions

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What is there to do in Winchester near my cottage?
Winchester has enough activities and sights to keep you on the hop for weeks, starting with Rock Harbor Golf Course. The Kernstown Battlefield, Museum of the Shenandoah Valley and Apple Blossom Mall are other fantastic attractions. If you're in town a while, Jim Barnett Park and Handley Regional Library are nice final touches to your itinerary.

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