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Our top choices for Winchester cottages

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
10.0 out of 10, Exceptional, (34 reviews)
"A very spacious and well equipped home to get away from it all; but, also convenient to Winchester for a night out. The fenced in areas for dogs were lovely."
United States
David A.
$446 nightly
The price is $492
Apr 22 - Apr 23
Total with taxes and fees
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

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 21 - Apr 22
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

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.
$387 nightly
The price is $430
Apr 21 - Apr 22
Total with taxes and fees
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

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.
$476 nightly
The price is $525
Apr 22 - Apr 23
Total with taxes and fees
The Vue - Mountain Top hot tub overlooking the Shenandoah River

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.
$278 nightly
The price is $309
Apr 21 - Apr 22
Total with taxes and fees
Peaceful Waterfall House -- 2 bedroom hidden treasure

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, (20 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!

Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets
Fort Valley
9.8 out of 10, Exceptional, (62 reviews)
"We enjoyed the hot tub, the views, and the easy check in/check out."
United States
Dakota B.
$230 nightly
The price is $253
May 1 - May 2
Total with taxes and fees
Cozy Retreat - Hot tub + Mountain Views + Pets

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
$369 nightly
The price is $396
Apr 21 - Apr 22
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg

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.
$274 nightly
The price is $316
Apr 21 - Apr 22
Total with taxes and fees
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

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.
$463 nightly
The price is $515
May 3 - May 4
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!

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.
$329 nightly
The price is $367
Apr 21 - Apr 22
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

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.
$345 nightly
The price is $393
Apr 21 - Apr 22
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
10.0 out of 10, Exceptional, (34 reviews)
"The hot tub worked well. The place was clean. The location was fantastic. I had no problems but somebody may want to run the blower on wood burner and if I didn’t have 4 wheel drive; I would not get in and out of drive. For me the stay was fantastic "
United States
Greg N.
$327 nightly
The price is $364
Apr 21 - Apr 22
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!

The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (46 reviews)
"Everything was beautiful. Thank you!"
United States
Michael W.
$179 nightly
The price is $199
Apr 26 - Apr 27
Total with taxes and fees
The Carriage House at Carrot Top Cottage

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!

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.
$444 nightly
The price is $489
Apr 21 - Apr 22
Total with taxes and fees
Indoor Sauna, Arcade & Hot Tub - Bryce Resort, Hiking & Shenandoah Wineries
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

Find out more about Winchester

Winchester Cottages information

Number of reviews
418
Accommodation
181 Cottages
Lowest Price
$199
Highest Price
$525

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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