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Secluded, Cozy Cottage in the Shenandoah Valley

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (162)
"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*
Smart TV, books

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

9.8 out of 10, Exceptional, (43)
"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 HK$1,423
HK$2,761 total
includes taxes & fees
5 Jan - 6 Jan 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
Bar (on property)

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
Smart TV, stereo

Cozy Retreat - Hot tub + Mountain Views + Pets

10.0 out of 10, Exceptional, (22)
"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 HK$681
HK$2,055 total
includes taxes & fees
6 Jan - 7 Jan 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!"
The price is HK$661
HK$1,288 total
includes taxes & fees
26 Dec - 27 Dec
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, (33)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is HK$2,138
HK$3,062 total
includes taxes & fees
30 Dec - 31 Dec
18th Century Stone Cottage minutes from historic Middleburg
Lost River WV-Relaxing 3br/2bath farmhouse-dog friendly- treetop deck-workspace
Fridge, microwave, oven, stovetop

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
2 bedrooms, WiFi, bed sheets

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
TV, Netflix, streaming services

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, (29)
"Wonderful "
Carrot Top Cottage surrounded by National Park
Hunt Country cottage in Upperville!
Private kitchen

Hunt Country cottage in Upperville!

10.0 out of 10, Exceptional, (13)
"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
Interior

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!
Interior

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

The price is HK$1,555
HK$2,828 total
includes taxes & fees
28 Dec - 29 Dec
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.
Outdoor dining

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.
Spacious Mtn Pet Friendly Home, Hottub, Firepit
Outdoor spa tub

Spacious Mtn Pet Friendly Home, Hottub, Firepit

Spacious Mtn Pet Friendly Home, Hottub, Firepit
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
Dining

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
RIVERKEEPER INN, Waterfront Property on the Potomac River
View from property

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (115)
"Went to Harper’s Ferry for our 25th wedding anniversary and wanted to stay near the water since we usually stay in town. Found this property and it was perfect. Sits on property with owners who we met and their dog Chloe who was an absolute sweetheart. If you are looking for a piece of serenity you will find it at the Riverkeeper Inn. Very nice and quiet neighborhood. The property was tidy and clean and you get to use the gazebo or decks near the water to chill and if it wasn’t too chilly would...
RIVERKEEPER INN, Waterfront Property on the Potomac River
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

Hidden Gem in the woods with hot tub
Property grounds

Hidden Gem in the woods with hot tub

9.6 out of 10, Exceptional, (66)
"Nice"
Hidden Gem in the woods with hot tub
Secluded, Cozy Cottage in the Shenandoah Valley

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (162)
"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
Terra Alta - Incredible River Views and Hot Tub!
Outdoor spa tub

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
The price is HK$2,115
HK$4,978 total
includes taxes & fees
26 Dec - 27 Dec
Terra Alta - Incredible River Views and Hot Tub!
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.

Frequently asked questions

Why book your cottage in Winchester with Expedia?
Expedia has some great cottages in Winchester, so get set for a memorable stay close to nature. If you need to stick to a budget, click on how much you want to spend and the preferred star rating of your property. Or, make use of our filters to search for cottages with free WiFi or a pool. We’ll help you find the right digs whatever your plans or bank balance.
How can I find cheap cottages in Winchester?
Expedia can help you locate cheap cottages in Winchester. To reserve a fantastic stay in a matter of clicks, try out our handy filter tool to tailor your search results by budget, amenities and star rating.
What is there to do in Winchester near my cottage?
You’ll find tons of fantastic things to sink your teeth into in Winchester. You won’t want to miss attractions like Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theatre. Winchester Little Theatre, Shenandoah University and Jim Barnett Park are other must-see’s.