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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

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.
$199 nightly
The price is $219
Apr 28 - Apr 29
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
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.
$392 nightly
The price is $436
Apr 27 - Apr 28
Total with taxes and fees
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Property grounds

The Vue - Mountain Top hot tub overlooking the Shenandoah River

The Vue - Mountain Top hot tub overlooking the Shenandoah River
Front Royal
10.0 out of 10, Exceptional, (20 reviews)
"Good communication from the host, very beautiful home with amazing scenery! Our group had a great time!"
United States
Devin P.
$430 nightly
The price is $475
May 11 - May 12
Total with taxes and fees
The Vue - Mountain Top hot tub overlooking the Shenandoah River
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, (22 reviews)
"The house had wonderful spaces to use for our weekend getaway!"
United States
Jessame P.
$318 nightly
The price is $354
Apr 29 - Apr 30
Total with taxes and fees
Lake View Retreat - Cottage Near a Peaceful Lake!
Outdoor spa tub

Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets
Fort Valley
9.8 out of 10, Exceptional, (64 reviews)
"We enjoyed the hot tub, the views, and the easy check in/check out."
United States
Dakota B.
$235 nightly
The price is $260
May 1 - May 2
Total with taxes and fees
Cozy Retreat - Hot tub + Mountain Views + Pets
Exterior

18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (58 reviews)
"Loved out stay! "
United States
Emilee
$372 nightly
The price is $399
Apr 27 - Apr 28
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
Exterior

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

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Luray
9.8 out of 10, Exceptional, (91 reviews)
"We loved our stay over NYE and the town of Luray had a great fireworks celebration. The dogs loved the backyard! "
United States
Jacob M.
$276 nightly
The price is $318
Apr 27 - Apr 28
Total with taxes and fees
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Exterior

Peaceful Waterfall House -- 2 bedroom hidden treasure

Peaceful Waterfall House -- 2 bedroom hidden treasure
Berkeley Springs
9.8 out of 10, Exceptional, (11 reviews)
"Absolutely our favorite rental by far! Everything was perfect. So very relaxing"
United States
Christine M.
$286 nightly
The price is $318
Apr 27 - Apr 28
Total with taxes and fees
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, (26 reviews)
"Great house and location! "
United States
Johanna S.
$324 nightly
The price is $362
Apr 29 - Apr 30
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
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, (21 reviews)
"Great view, very secluded"
United States
Matt s.
$340 nightly
The price is $378
Apr 30 - May 1
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
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, (25 reviews)
"Lovely views, very spacious, well appointed in terms of kitchen."
United States
sharyn m.
$419 nightly
The price is $466
May 5 - May 6
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
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
9.8 out of 10, Exceptional, (16 reviews)
"Absolutely amazing place and stay! I could not possibly be more impressed and I look forward to coming back."
United States
Jasmine M.
$347 nightly
The price is $396
Apr 27 - Apr 28
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
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, (47 reviews)
"We enjoyed the stay and it was an easy walk to the places we wanted to go!"
United States
Mike S.
$179 nightly
The price is $199
Apr 27 - Apr 28
Total with taxes and fees
The Carriage House at Carrot Top Cottage
Terrace/patio

Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
10.0 out of 10, Exceptional, (35 reviews)
"The house is lovely and clean, and has a great view of the lake. We reserved during the winter and couldn’t use the lake but would love to return in warmer weather to be able to use more of the outdoors. "
United States
Cathy W.
$355 nightly
The price is $395
Apr 28 - Apr 29
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain 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.
$300 nightly
The price is $334
Apr 27 - Apr 28
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
Exterior

Indoor Sauna, Arcade & Hot Tub - Bryce Resort, Hiking & Shenandoah Wineries

Indoor Sauna, Arcade & Hot Tub - Bryce Resort, Hiking & Shenandoah Wineries
Mount Jackson
10.0 out of 10, Exceptional, (2 reviews)
"The property was clean, well maintained and easily accommodated two families with small children. The kitchen and rooms were equipped with all the essentials. The hosts were pleasant and very responsive. "
United States
Dani A.
$443 nightly
The price is $489
May 5 - May 6
Total with taxes and fees
Indoor Sauna, Arcade & Hot Tub - Bryce Resort, Hiking & Shenandoah Wineries
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)
"Great place to stay! Well decorated, equipped and spacious! Outdoor fire pit and a huge stack of firewood was a nice bonus"
United States
Steve S.
$478 nightly
The price is $550
May 11 - May 12
Total with taxes and fees
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Very clean and up to date. Staff very personable. "
William 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
451
Accommodation
181 Cottages
Lowest Price
$199
Highest Price
$550

Frequently asked questions

Why book your cottage in Winchester with Expedia?
We think that vacations should be simple, so if you're in search of cottages in Winchester at a competitive price, Expedia has got your back. Keep costs down and check in to a cheap option far away from the city rush, or splurge on an upmarket cottage to spoil your favorite people.
How can I find cheap cottages in Winchester?
The easiest way to locate cheap cottages in Winchester is with Expedia's useful filter tool. Narrow your search results by star rating, amenities and budget to snag awesome prices in just a few keystrokes.
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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