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Beautiful 360 views!
Exterior
Beautiful 360 views!
10.0 out of 10, Exceptional, (171)
"Perfect place to relax and unwind after spending the day hiking at Shenandoah. Hot tub was a great amenity. Cottage was clean and well stocked. Owners are very nice."
Beautiful 360 views!
Lovettsville Cottage in Heart of Wine Country
TV, Netflix, streaming services
Lovettsville Cottage in Heart of Wine Country
10.0 out of 10, Exceptional, (28)
"Family reunion to get 3 sisters together. My Mother-in-Law is 90 and we drove to VA so she can visit with her 88 and 80 year old sisters. We did have an issue wtih the 2 statements below provided in an email on 9Sept2024, which is after the window for cancelation. The homeowner isn't just next door, they are adjoining, which isn't clear in the description. It is also not shown in the pictures. We expected quiet time for morning coffee outdoors, instead we were able to hear the homeowner on...
Lovettsville Cottage in Heart of Wine Country
Hunt Country cottage in Upperville!
Private kitchen
Hunt Country cottage in Upperville!
9.8 out of 10, Exceptional, (10)
"Super cute place literally 5 minutes from the show grounds. "
Hunt Country cottage in Upperville!
Our Cottage is in Historical Luray, Walking Distance of Town Restaurants & Shops
Exterior
Our Cottage is in Historical Luray, Walking Distance of Town Restaurants & Shops
10.0 out of 10, Exceptional, (231)
"Highly recommend "
Our Cottage is in Historical Luray, Walking Distance of Town Restaurants & Shops
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, (39)
"We had a lovely stay in Tyler's home. It was perfect for my husband and I and our two adult children. It was conveniently located to Luray Caverns and Shenandoah Park, as well as grocery stores and restaurants. I especially liked the updated finishes, large kitchen, washer and dryer and the fenced back yard with fire pit and charcoal grill. Tyler was very quick to respond to any questions I had. I would definitely stay again. Minor gripe would be the back bedroom lacked any storage for clothing...
The price is HK$1,243
HK$2,554 total
includes taxes & fees
24 Nov - 25 Nov
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
The Carriage House at Carrot Top Cottage
Aerial view
The Carriage House at Carrot Top Cottage
9.8 out of 10, Exceptional, (28)
"My wife and I had a fantastic time. Very warm and cozy cottage. Walking distance to everything, but tucked away enough to enjoy your privacy. Would definitely stay with them again."
The price is HK$762
HK$1,313 total
includes taxes & fees
19 Nov - 20 Nov
The Carriage House at Carrot Top Cottage
Welcome to the “old town cottage”
Fridge, microwave, oven, stovetop
Welcome to the “old town cottage”
10.0 out of 10, Exceptional, (60)
"This is our second time staying at the Cottage. Another enjoyable family weekend in Warrenton. Chase is a very kind host!"
Welcome to the “old town cottage”
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
2.0 star property
10.0 out of 10, Exceptional, (6)
"We enjoyed our stay at the home, and it was very convenient to well-known Bolivar eats and a reasonable walk to the main part of Harper's Ferry if you are a walker. We enjoyed sitting in the side yard and chatting, walking across the street to Kelly Farm Kitchen and the Bolivar Bread Co. 2 things that were "as advertised" but may not work for you. 1) The spiral stair is tight. Seeing how the first floor lays out, it was likely chosen to maximize the living space on level 1. I am a petite 5'1"...
The price is HK$1,282
HK$2,361 total
includes taxes & fees
17 Nov - 18 Nov
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
RIVERKEEPER INN, Waterfront Property on the Potomac River
View from property
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, (113)
"Enjoyed sitting on the deck above the river in the evenings, quiet and peaceful looking forward to staying there again."
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, (36)
"If I could give 10 stars, I would! This cabin in Paris, VA was everything I was looking for and more. Clean, spacious, quiet, and comfortable. The arboretum up the road was also a nice treat to enjoy. I can't wait to come back for another stay. "
The price is HK$1,313
HK$2,360 total
includes taxes & fees
10 Nov - 11 Nov
Historical cottage in the town of Paris
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds
Lake View Retreat - Cottage Near a Peaceful Lake!
9.6 out of 10, Exceptional, (14)
"This property was a perfect place to stay for our group. While it was a little out of the way, it suited our needs, was clean, and very comfortable. The owners made quick communication with them easy. Definitely recommend!"
The price is HK$1,407
HK$3,539 total
includes taxes & fees
10 Nov - 11 Nov
Lake View Retreat - Cottage Near a Peaceful Lake!
Cozy Retreat - Hot tub + Mountain Views + Pets
Smart TV, stereo
Cozy Retreat - Hot tub + Mountain Views + Pets
10.0 out of 10, Exceptional, (20)
"Beautiful location, great hot tub and friendly owner "
The price is HK$776
HK$2,194 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Retreat - Hot tub + Mountain Views + Pets
Cozy cottage located at our winery at the base of Old Rag and Shenandoah Park.
Exterior
Cozy cottage located at our winery at the base of Old Rag and Shenandoah Park.
10.0 out of 10, Exceptional, (1)
"The area was lovely and Jimm was so kind and made sure we had everything we needed for our stay. He also made it very easy to get into our cottage. Communication was top notch!"
Cozy cottage located at our winery at the base of Old Rag and Shenandoah Park.
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Dining
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
9.6 out of 10, Exceptional, (9)
"We enjoyed the beautifully decorated river house. The hot tub was a treat each evening along with a relaxing fire by the river. We even enjoyed sitting on the back deck watching the birds. The bed was comfy and the kitchen was nicely stocked. We loved our vacation!!"
The price is HK$2,522
HK$3,706 total
includes taxes & fees
10 Nov - 11 Nov
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Secluded, Cozy Cottage in the Shenandoah Valley
Secluded, Cozy Cottage in the Shenandoah Valley
10.0 out of 10, Exceptional, (159)
"We had a very romantic and beautiful honeymoon here, I can't recommend it enough. The sunrises were incredible!"
Secluded, Cozy Cottage in the Shenandoah Valley
Bear Chase Cottage
Property grounds
Bear Chase Cottage
10.0 out of 10, Exceptional, (30)
"Wanted to stay near the Bleu Frog Vinyard for a USNA company/class reunion. Main purpose was to watch the Navy/Air Force and enjoy local wine & beer. Bear Chase Cottage was perfectly located. It was clean and well appointed. The local brewing offered excellent food and hiking trails we're very convenient. Navy won handily making for a most enjoyable weekend. Beat Army!"
Bear Chase Cottage
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, (52)
"We had a fabulous weekend at the Farmhouse. Comfy, clean, and well-equipped, it was the perfect home base for hiking in Lost River State Park. Sunset on the deck, stargazing in the field…we had a great time!"
Lost River WV-Relaxing 3br/2bath farmhouse-dog friendly- treetop deck-workspace
Peaceful Lakefront Cottage with Mountain Views!
Fridge, microwave, oven, stovetop
Peaceful Lakefront Cottage with Mountain Views!
10.0 out of 10, Exceptional, (21)
"Really enjoyed stay home was great "
The price is HK$1,748
HK$4,182 total
includes taxes & fees
5 Dec - 6 Dec
Peaceful Lakefront Cottage with Mountain Views!
LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!
Beach
LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!
10.0 out of 10, Exceptional, (157)
"Cabin was as listed with plenty of towels and little touches. Cooking pans were on the better side, which is unusual for a rental. Screened porch gives guests a chance to enjoy the serene atmosphere without the issue of nature's little biting critters. Bed was comfortable and after figuring out where the heat source was, it kept us very comfortable. Plenty of space for the two of us. "
LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!
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!"
The price is HK$2,324
HK$2,985 total
includes taxes & fees
14 Nov - 15 Nov
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
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

Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor dining
Dreamtime - Modern A-frame Cabin w/ Hot tub
10.0 out of 10, Exceptional, (34)
"The cabin was in a beautiful community and setting with a fabulous outdoor area facing the woods. Many amenities in the home that made our stay easy with nicely renovated interior. Owner was very willing and able to offer help with anything and was receptive to feedback. Thank you!"
The price is HK$2,324
HK$2,957 total
includes taxes & fees
3 Dec - 4 Dec
Dreamtime - Modern A-frame Cabin w/ Hot tub
Star view cabin-Riverfront
Property grounds
Star view cabin-Riverfront
9.8 out of 10, Exceptional, (297)
"Great stay. Incredible views. Perfect weekend getaway. If you want to have a nice dinner bring your own glassware. Supplies were minimal in the house. "
Star view cabin-Riverfront
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Miscellaneous
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
10.0 out of 10, Exceptional, (356)
"This property was perfectly isolated. We felt like we were all alone in nature. The accommodations were also 1st class. We had everything we needed to ensure an awesome stay!!"
Secluded Mountain Home Features Breathtaking Valley 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.