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Next weekend
3 Oct - 5 Oct
In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
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21 Nov - 23 Nov

Featured Cottages in Winchester

Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!
Exterior

Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!

10.0 out of 10, Exceptional, (184)
"Very peaceful place only 2.5 miles from Luray. Everything you need to cook a meal, a very comfortable bed, and a great view. I will most likely stay here again when I travel this way in the future. "
Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Exterior

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

10.0 out of 10, Exceptional, (75)
"Perfect for hiking trails along Skyline Drive. Luray is a cute town with plenty to do nearby."
The price is NZ$603
includes taxes & fees
9 Oct - 10 Oct
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Secluded, Cozy Cottage in the Shenandoah Valley
Exterior

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (185)
"Great place to get away for the weekend! Very private and quiet! "
Secluded, Cozy Cottage in the Shenandoah Valley
Hunt Country cottage in Upperville!
Exterior

Hunt Country cottage in Upperville!

10.0 out of 10, Exceptional, (22)
"Beautiful cottage!! Incredibly comfortable! Loved it!!"
Hunt Country cottage in Upperville!
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Exterior

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

10.0 out of 10, Exceptional, (14)
"extremely quiet cabin in the woods"
The price is NZ$695
includes taxes & fees
30 Sept - 1 Oct
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (48)
"we enjoy our stay everytime"
Historical cottage in the town of Paris
Cozy Retreat - Hot tub + Mountain Views + Pets
Outdoor spa tub

Cozy Retreat - Hot tub + Mountain Views + Pets

9.8 out of 10, Exceptional, (51)
"We loved our stay! The house was perfect and my girls just loved all the charm and little touches. The views on the property were gorgeous and it was a perfect location."
The price is NZ$531
includes taxes & fees
5 Oct - 6 Oct
Cozy Retreat - Hot tub + Mountain Views + Pets
CEDAR LANE - Private Cottage, Sophisticated Country Charm
Terrace/patio

CEDAR LANE - Private Cottage, Sophisticated Country Charm

10.0 out of 10, Exceptional, (150)
"We have stayed here before and love it so much! Perfectly appointed, idyllic setting!"
CEDAR LANE - Private Cottage, Sophisticated Country Charm
Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond
Exterior

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond
Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns
Exterior

Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns

9.6 out of 10, Exceptional, (219)
"After several weeks of camping in the cold and rain, we looked forward to a quiet and comfortable stay and we found it on Old Mine Road."
Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns
Quaint Mini Cottage in Shepherdstown - Walking Distance
Dining

Quaint Mini Cottage in Shepherdstown - Walking Distance

8.0 out of 10, Very good, (3)
"Great, easy to find location. Nancy was a great communicator A wonderful option for us, as we were in the area for a wedding in Sharpsburg where overnight accommodations were a bit slim. Shepherdstown was a cute town with lots of cute local shops and places to eat. Would stay here again! "
Quaint Mini Cottage in Shepherdstown - Walking Distance
Cottage w/ Hot Tub and 100-Mile Valley Views!
Property grounds

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

10.0 out of 10, Exceptional, (19)
"Pretty cabin with a wonderful view, especially from the hot tub. We will return!"
The price is NZ$649
includes taxes & fees
2 Oct - 3 Oct
Cottage w/ Hot Tub and 100-Mile Valley Views!
LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!
Terrace/patio

LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!

10.0 out of 10, Exceptional, (168)
"We enjoyed ourselves "
LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Property grounds

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

9.8 out of 10, Exceptional, (6)
"It was a great place to starve whole experience was perfect. "
The price is NZ$680
includes taxes & fees
28 Sept - 29 Sept
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Cozy retreat near Old Rag
Property grounds

Cozy retreat near Old Rag

9.8 out of 10, Exceptional, (40)
"Our stay was beautiful in this mountain cabin! Jerry was a very accommodating and polite host. The cabin was beautiful and clean. We were close to wineries and hiking in Shanendoah National Park. We will be sure to look back here for our next vacation!"
Cozy retreat near Old Rag
Peaceful Waterfall House -- 2 bedroom hidden treasure
Exterior

Peaceful Waterfall House -- 2 bedroom hidden treasure

9.6 out of 10, Exceptional, (9)
"What a nice, history rich house to stay in. You can tell it has old bones but has been maintained and is full of character. Loved the relaxing setting with the river running around the house. Plenty to explore on the property down by the water and in the woods. Exactly what’s needed for a relaxing get away. Close to town as well for anything needed. Kirsten was a great host. "
The price is NZ$543
includes taxes & fees
1 Oct - 2 Oct
Peaceful Waterfall House -- 2 bedroom hidden treasure
The Vue - Mountain top hot tub overlooking the Shenandoah River
Property grounds

The Vue - Mountain top hot tub overlooking the Shenandoah River

2.0 star property
9.8 out of 10, Exceptional, (7)
"Love the view and beautiful appointed decor throughout the home…"
The price is NZ$851
includes taxes & fees
13 Oct - 14 Oct
The Vue - Mountain top hot tub overlooking the Shenandoah River
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (45)
"The home was impeccably clean, quiet, comfortable, and homey. We enjoyed our stay so much. The home was wonderfully decorated. "
Carrot Top Cottage surrounded by National Park
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Property grounds

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

9.8 out of 10, Exceptional, (7)
"Our rental space was on the top floor and the area was nice for our getaway. Host was quick to reply when we had a question. I would stay here again."
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Raspberry Retreat Cottage
Outdoor dining

Raspberry Retreat Cottage

10.0 out of 10, Exceptional, (3)
"Cute property. Beautiful scenery. This property worked well for our family."
Raspberry Retreat Cottage
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

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

10/10 Excellent
"Very friendly staff and clean facilities."
Patty 1-night trip
Posted 1 day ago
Courtyard by Marriott Winchester

Find out more about Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
1,232
Accommodation
192 Cottages
Lowest Price
NZ$531
Highest Price
NZ$851

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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