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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

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.
$201 nightly
The price is $221
May 3 - May 4
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
May 3 - May 4
Total with taxes and fees
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
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

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.
$327 nightly
The price is $364
May 3 - May 4
Total with taxes and fees
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, (21 reviews)
"Great view, very secluded"
United States
Matt s.
$335 nightly
The price is $373
May 4 - May 5
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.
$404 nightly
The price is $450
May 5 - May 6
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Exterior

Peaceful Waterfall House -- 2 bedroom hidden treasure

Peaceful Waterfall House -- 2 bedroom hidden treasure
Berkeley Springs
9.8 out of 10, Exceptional, (12 reviews)
"Absolutely our favorite rental by far! Everything was perfect. So very relaxing"
United States
Christine M.
$283 nightly
The price is $315
May 1 - May 2
Total with taxes and fees
Peaceful Waterfall House -- 2 bedroom hidden treasure
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
$367 nightly
The price is $394
May 6 - May 7
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
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
May 3 - May 4
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Exterior

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

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Luray
9.8 out of 10, Exceptional, (92 reviews)
"Our Host was very responsive and flexible, the home was well equipped, clean, and had plenty of room and conveniences to make our stay excellent."
United States
Joseph S.
$276 nightly
The price is $318
May 4 - May 5
Total with taxes and fees
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
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.
$334 nightly
The price is $372
May 3 - May 4
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
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.
$363 nightly
The price is $405
May 5 - May 6
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!
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.
$180 nightly
The price is $200
May 5 - May 6
Total with taxes and fees
The Carriage House at Carrot Top Cottage
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.
$306 nightly
The price is $341
May 5 - May 6
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
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.
$430 nightly
The price is $494
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

Hampton Inn Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"Excellent place to stay with lots of restaurants and stores nearby"
Robert 1-night trip
Posted 7 hours ago
Hampton Inn Martinsburg

Find out more about Winchester

Winchester Cottages information

Number of reviews
431
Accommodation
181 Cottages
Lowest Price
$200
Highest Price
$494

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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