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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Winchester

RIVERKEEPER INN, Waterfront Property on the Potomac River
Terrace/patio

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (125)
"Riverkeeper Inn is located in a peaceful and quiet area of Harpers Ferry, equally perfect in early mornings and late nights. The check-in and check-out process were very easy, and the property itself had everything we could've asked for, and then some."
RIVERKEEPER INN, Waterfront Property on the Potomac River
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (45)
"This is a nice home near sky meadow park. A great place to see the stars... Very close to DC. "
Historical cottage in the town of Paris
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, (179)
"I loved my stay! The cottage was clean and cozy, and being able to use the hot tub was amazing. Ed and Betsy and all the animals were welcoming. The cottage was especially beautiful during sunrise. A very peaceful environment to stay in. "
Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (15)
"Very nice property with convenient location! Within walking distance of down town. "
The price is NZ$554
includes taxes & fees
17 Aug - 18 Aug
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Outdoor spa tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

9.8 out of 10, Exceptional, (12)
"We loved the property and the access to the river."
The price is NZ$618
includes taxes & fees
24 Aug - 25 Aug
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (46)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is NZ$661
includes taxes & fees
12 Aug - 13 Aug
18th Century Stone Cottage minutes from historic Middleburg
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, (216)
"Amazing and relaxing"
Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns
Wild Hare Cottage
Terrace/patio

Wild Hare Cottage

10.0 out of 10, Exceptional, (7)
"We had just a quick overnight stay, the cottage is cozy, clean, and charming. Communication was easy and clear, we'd love to stay again!"
The price is NZ$398
includes taxes & fees
13 Aug - 14 Aug
Wild Hare Cottage
Raspberry Retreat Cottage
Outdoor dining

Raspberry Retreat Cottage

Raspberry Retreat Cottage
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Terrace/patio

Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.

9.4 out of 10, Exceptional, (11)
"Convenient to where I needed to be. Nice property. Dogs loved the property"
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Secluded, Cozy Cottage in the Shenandoah Valley
Exterior

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (180)
"A real cute place with a cozy layout and amazing bathroom and shower. It was just secluded enough but not overly challenging to get to. The upper porch was great for hanging out and watching the pair of hummingbirds that seem to have made the area home. The bed was comfortable but also a little squeaky and noisy. We really enjoyed our stay and it was just the relaxing getaway we needed. "
Secluded, Cozy Cottage in the Shenandoah Valley
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (39)
"We had a great family trip here! Close to everything that Harper’s Ferry has to offer! Highly recommend this cute cabin for your trip!"
Carrot Top Cottage surrounded by National Park
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Outdoor dining

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (20)
"Loved this house for relaxing, enjoying nature and reconnecting with friends!"
The price is NZ$1,007
includes taxes & fees
28 Aug - 29 Aug
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Cozy Mountain Cottage - Perfect for Friends, Family
Exterior

Cozy Mountain Cottage - Perfect for Friends, Family

10.0 out of 10, Exceptional, (14)
"We had a great time over Thanksgiving. The house , yard and host were all great. I woood definitely stay here again. "
Cozy Mountain Cottage - Perfect for Friends, Family
Lovettsville Cottage in Heart of Wine Country
Outdoor dining

Lovettsville Cottage in Heart of Wine Country

9.8 out of 10, Exceptional, (34)
"We stayed here for a few days over the Thanksgiving holiday. It was cozy, comfortable, and had all the great comforts of a home away from home. "
Lovettsville Cottage in Heart of Wine Country
Lost River Swiss Cottage/10 acres/Private Dog Park/Streams
Exterior

Lost River Swiss Cottage/10 acres/Private Dog Park/Streams

9.8 out of 10, Exceptional, (129)
"Beautiful property Beautiful views It is located down gravel lane Nice beds living space"
Lost River Swiss Cottage/10 acres/Private Dog Park/Streams
Cozy Retreat - Hot tub + Mountain Views + Pets
Outdoor spa tub

Cozy Retreat - Hot tub + Mountain Views + Pets

9.8 out of 10, Exceptional, (47)
"It’s was a beautiful stay for me and my partner we got to spend quality time together "
The price is NZ$476
includes taxes & fees
9 Sept - 10 Sept
Cozy Retreat - Hot tub + Mountain Views + Pets
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

9.8 out of 10, Exceptional, (10)
"Good place for a nice quite weekend."
The price is NZ$594
includes taxes & fees
11 Aug - 12 Aug
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Lake View Retreat - Cottage Near a Peaceful Lake!
Exterior

Lake View Retreat - Cottage Near a Peaceful Lake!

9.6 out of 10, Exceptional, (18)
"Was really able to relax and enjoy during our brief stay. Would come again."
The price is NZ$609
includes taxes & fees
12 Aug - 13 Aug
Lake View Retreat - Cottage Near a Peaceful Lake!
Peaceful Waterfall House -- 2 bedroom hidden treasure
Exterior

Peaceful Waterfall House -- 2 bedroom hidden treasure

9.6 out of 10, Exceptional, (5)
"Very peaceful "
The price is NZ$530
includes taxes & fees
20 Aug - 21 Aug
Peaceful Waterfall House -- 2 bedroom hidden treasure
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

10/10 Excellent
"The property was very clean, in great condition, and quiet. Breakfast was good. Breakfast selections about average for similar hotels. The breakfast host was VERY friendly. "
Michael 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Winchester

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.