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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

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 NZ$372
includes taxes & fees
3 June - 4 June
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
9.8 out of 10, Exceptional, (12 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is NZ$794
includes taxes & fees
31 May - 1 June
Apple Mountain House • Hot Tub • Game Room
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 NZ$732
includes taxes & fees
26 May - 27 May
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Terrace/patio

All-Inclusive 4BR • Mountain Views • Hot Tub

All-Inclusive 4BR • Mountain Views • Hot Tub
Front Royal
The price is NZ$775
includes taxes & fees
14 June - 15 June
All-Inclusive 4BR • Mountain Views • Hot Tub
Outdoor spa tub

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, (35 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.
The price is NZ$1,160
includes taxes & fees
7 June - 8 June
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Exterior

The VUE • Mountaintop 4BR • Hot Tub & Views

The VUE • Mountaintop 4BR • Hot Tub & Views
Front Royal
10.0 out of 10, Exceptional, (21 reviews)
"Good communication from the host, very beautiful home with amazing scenery! Our group had a great time!"
United States
Devin P.
The price is NZ$1,008
includes taxes & fees
2 June - 3 June
The VUE • Mountaintop 4BR • Hot Tub & 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, (22 reviews)
"The house had wonderful spaces to use for our weekend getaway!"
United States
Jessame P.
The price is NZ$615
includes taxes & fees
2 June - 3 June
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, (22 reviews)
"Great view, very secluded"
United States
Matt s.
The price is NZ$644
includes taxes & fees
27 May - 28 May
Cottage w/ Hot Tub and 100-Mile Valley Views!
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, (17 reviews)
"GREAT stay…loved the location, the hot tub, the amenities, and the host."
United States
Domenic E.
The price is NZ$669
includes taxes & fees
25 May - 26 May
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
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)
"The host was prompt with answering any inquiries. The house was well stocked. Great area to visit."
United States
Ellen B.
The price is NZ$998
includes taxes & fees
2 June - 3 June
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
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 NZ$581
includes taxes & fees
8 June - 9 June
Woodsy Retreat with a Hot Tub and Seasonal 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)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is NZ$343
includes taxes & fees
25 May - 26 May
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.
The price is NZ$834
includes taxes & fees
8 June - 9 June
Peaceful Lakefront Cottage with 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, (13 reviews)
"House was great, though a little cold for the winter. Perfect place to get away! "
United States
Krystal A.
The price is NZ$534
includes taxes & fees
26 May - 27 May
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 NZ$632
includes taxes & fees
21 June - 22 June
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (60 reviews)
"Loved out stay! "
United States
Emilee
The price is NZ$674
includes taxes & fees
9 June - 10 June
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, (93 reviews)
"House was cozy and clean and the hosts very helpful. Perfect for our long weekend! "
United States
Kelly J.
The price is NZ$554
includes taxes & fees
28 May - 29 May
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
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

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

6/10 Okay
"We arrived late due to weather and traffic Approximately 12:40am. At 5:30am our smoke detector beeped non-stop as if the battery was dead Because of our exhaustion we did not want maintenance in our room to address it. While checking out I was told they could only offer a 30% discount on our next stay because we booked with you. They would send us an email. We will see. Meanwhile he stated that it happened in a few rooms last night"
Patricia 1-night trip
Posted 2 hours ago
Fairfield Inn & Suites by Marriott Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
460
Accommodation
181 Cottages
Lowest Price
NZ$343
Highest Price
NZ$1,160

Frequently asked questions

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 Harbour 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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