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Compare 156 Cottages in Winchester with updated reviews, rates, and availability.

Secluded, Cozy Cottage in the Shenandoah Valley
Quiet nights and so many stars.

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (163)
"It's the perfect cozy place for two for Thanksgiving. The indoor fireplace has plenty of firewood, and the outdoor firepit has a grill plate, perfect for making smores. We started our mornings having coffee in the hot tub. We will stay here again! "
Secluded, Cozy Cottage in the Shenandoah Valley
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Living area

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

9.8 out of 10, Exceptional, (44)
"I loved this property! The inside was so cute and clean, and the property managers were very responsive to any questions we had. "
The price is AED 588
AED 1,203 total
includes taxes & fees
6 Jan - 7 January 2025
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (38)
"What a lovely and comfortable cottage! "
Historical cottage in the town of Paris
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Fire pit w/custom Adirondack chairs, solar Tiki torches, grapevine arbor

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

9.8 out of 10, Exceptional, (21)
"We enjoyed our stay at the cottage. We were 15-20 minutes away from lots of breweries and outdoor dining places yet felt like we were staying in the country. Enjoyed the hot tub and basketball hoop and the fire pit was ready for us when we arrived. Our little dog was welcomed and enjoyed the yard too. Great communication with the owner. There is some noise from the train and road nearby but it did not bother us."
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Cozy Retreat - Hot tub + Mountain Views + Pets
Exterior

Cozy Retreat - Hot tub + Mountain Views + Pets

10.0 out of 10, Exceptional, (24)
"This cottage is so cute and it fit the four of us just right. Very comfortable beds, lots of pillows and nice living room furniture. There are great views of the mountains and big fields with cows on the other side of the fence. You felt like you were far away from the ruckus of everyday life. It was bright and cheery with beautiful wall paper and lots of windows. A hot tub and screened porch was also there to enjoy. We had a wonderful time and will go back again. "
The price is AED 295
AED 945 total
includes taxes & fees
6 Jan - 7 January 2025
Cozy Retreat - Hot tub + Mountain Views + Pets
Quiet tiny home. Dog-friendly. Private fenced yard
Terrace/patio

Quiet tiny home. Dog-friendly. Private fenced yard

9.6 out of 10, Exceptional, (5)
"I stayed for a few nights over Thanksgiving and this was the perfect place for my dog and I! She loved the backyard and it was walking distance to Jefferson Rock and other trails snd things to see in Harpers Ferry. It was clean and in a very safe and quiet neighborhood. Would definitely come back!"
Quiet tiny home. Dog-friendly. Private fenced yard
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (34)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is AED 1,010
AED 1,446 total
includes taxes & fees
5 Jan - 6 January 2025
18th Century Stone Cottage minutes from historic Middleburg
Bear Chase Cottage
Living area

Bear Chase Cottage

10.0 out of 10, Exceptional, (32)
"The cabin was perfect! Clean and cozy. We wish we could have extended our stay! We will definitely come back! "
Bear Chase Cottage
Lost River WV-Relaxing 3br/2bath farmhouse-dog friendly- treetop deck-workspace
Front of the farmhouse

Lost River WV-Relaxing 3br/2bath farmhouse-dog friendly- treetop deck-workspace

9.8 out of 10, Exceptional, (55)
"We had a great stay! The house was fully loaded with everything we needed and the location was great! Would definitely stay again!! "
Lost River WV-Relaxing 3br/2bath farmhouse-dog friendly- treetop deck-workspace
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
Exterior

Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery

10.0 out of 10, Exceptional, (13)
"The house was super cute and the location was perfect!"
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
Lovettsville Cottage in Heart of Wine Country
Lovettville Vacation Rental | 1BR | 2BA | 2 Stories | 3 Steps Required

Lovettsville Cottage in Heart of Wine Country

9.8 out of 10, Exceptional, (31)
"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
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (30)
"Wonderful "
Carrot Top Cottage surrounded by National Park
Hunt Country cottage in Upperville!
Living area

Hunt Country cottage in Upperville!

10.0 out of 10, Exceptional, (14)
"This adorable home was the perfect stay during our visit to Middleburg which was a quick drive from upperville. We'll be back!"
Hunt Country cottage in Upperville!
Riversong Luxe Cabin w/ Fire Pit on North River
Exterior

Riversong Luxe Cabin w/ Fire Pit on North River

3.0 star property
Riversong Luxe Cabin w/ Fire Pit on North River
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Terrace/patio

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

The price is AED 918
AED 1,558 total
includes taxes & fees
6 Jan - 7 January 2025
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
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, (8)
"Place was clean ..had all the necessary bath and kitchen items. Very convenient to historic part of Harpers Ferry.. Large fenced backyard for our dog… Would give it 5 stars but winding , circular metal stairway was very tight.Fortunately both of us are slim so was manageable. Plan on staying here again if visiting Harper’s Ferry/Charles Town area.."
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
COZY CABIN. One room cottage with loft.
Exterior

COZY CABIN. One room cottage with loft.

10.0 out of 10, Exceptional, (3)
"My friend and I came up to do some biking on the C&O and western Maryland rail trail, and to also do some hiking! Weather was perfect and the cozy cabin fit all our needs perfectly!. Very cutely decorated…Clean…Beautiful views. The host even invited us for dinner one night if we wanted to join them! Check in was easy and there was even a few snacks and waters provided. All very thoughtful gestures. We were warned that there was a two mile stretch of rougher road leading up to the cabin but...
COZY CABIN. One room cottage with loft.
Close to Hiking | Hot Tub | Fire Pit | Pets OK
Our deck is great for relaxing and enjoying the outdoors

Close to Hiking | Hot Tub | Fire Pit | Pets OK

Close to Hiking | Hot Tub | Fire Pit | Pets OK
The Winemakers Cottage at Barrel Oak Winery & Brewery
Exterior

The Winemakers Cottage at Barrel Oak Winery & Brewery

2.0 star property
The Winemakers Cottage at Barrel Oak Winery & Brewery
Pet-friendly Virginia Cabin: 3 Mi to Luray Caverns
Property grounds

Pet-friendly Virginia Cabin: 3 Mi to Luray Caverns

3.0 star property
10.0 out of 10, Exceptional, (1)
Pet-friendly Virginia Cabin: 3 Mi to Luray Caverns
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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Other property types in Winchester

Secluded, Cozy Cottage in the Shenandoah Valley
Quiet nights and so many stars.

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (163)
"It's the perfect cozy place for two for Thanksgiving. The indoor fireplace has plenty of firewood, and the outdoor firepit has a grill plate, perfect for making smores. We started our mornings having coffee in the hot tub. We will stay here again! "
Secluded, Cozy Cottage in the Shenandoah Valley
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Riverview from covered deck area

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.4 out of 10, Exceptional, (329)
"Amazing!!!"
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Living Room

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (88)
"Great year round location. Owners are nearby if issues occur. HIGHLY RECOMMENDED. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
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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