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Compare 157 Cottages in Winchester with updated reviews, rates, and availability.

Secluded, Cozy Cottage in the Shenandoah Valley
10.0 out of 10, Exceptional, (155)
"This house is everything and more! The surrounding area is perfect for hiking. The porches and fire pit are perfect for sitting and relaxing. It rained during our stay and I loved sitting on the upper porch watching it. It is absolutely as shown in the listing. I loved all the cute fall touches and I want a shower just like the one here. We will definitely be back!! Thank you for a relaxing weekend. "
Secluded, Cozy Cottage in the Shenandoah Valley
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
9.8 out of 10, Exceptional, (37)
"This place was REALLY nice. Beautiful outdoor space with fenced yard. Perfect for us and our dog. Everything you need was there. Quiet neighborhood and close to Luray Caverns (5-10 min) and Shenandoah National Park Thornton Gap entrance (15 min). "
The price is AED 588
AED 1,211 total
includes taxes & fees
30 Sep - 1 Oct
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Bear Mountain Cottage
10.0 out of 10, Exceptional, (5)
"The cottage is immaculate and nicely decorated. While it's located in the woods, it's just minutes away from town and close to many wineries. Would definitely consider staying here in the future and recommend to our friends."
Bear Mountain Cottage
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.2 out of 10, Wonderful, (111)
"We had a wonderful weekend! Everything was perfect. Great human hosts and dog host! Thank you!"
RIVERKEEPER INN, Waterfront Property on the Potomac River
Our Cottage is in Historical Luray, Walking Distance of Town Restaurants & Shops
10.0 out of 10, Exceptional, (225)
"The place was really homey. Groceries and Luray Caverns are just 5 min away. It is also close to Shenandoah Stony Man hiking trail. Will definitely come again if we are back next time!"
Our Cottage is in Historical Luray, Walking Distance of Town Restaurants & Shops
Lovettsville Cottage in Heart of Wine Country
10.0 out of 10, Exceptional, (27)
"This was such a nice place to stay while in Virginia visiting family! The area is full of antiques, wineries, breweries and gorgeous scenery. The cabin itself is on a pretty piece of property with a well-kept large lawn and attached to the main house, though it felt very private and we never heard the occupants. It was very comfortable and clean. Keep in mind most places in the this rural area are on some kind of gravel road. Expect to wash your car:) I will definitely book this one again! "
Lovettsville Cottage in Heart of Wine Country
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
2.0 star property
10.0 out of 10, Exceptional, (4)
"Sizeable backyard with nice amenities for entertaining. Bathrooms were large with plenty of hot water. AC was excellent throughout the property. Spiral staircase was narrow but manageable for small children and moderately mobility impaired adults. Would stay again. "
The price is AED 680
AED 1,198 total
includes taxes & fees
20 Oct - 21 Oct
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (26)
"My husband and I had a wonderful stay in this charming, well equipped house located in an ideal spot for local hiking and fine dining. The upstairs bedroom is spacious, but cozy, and has a nice area for reading and doing work. Downstairs is a small kitchen, comfy couch and large TV. We sat outside for our morning coffee overlooking the Blue Ridge Mountain-- and our host couldn't be more accommodating and friendly! Highly recommend."
18th Century Stone Cottage minutes from historic Middleburg
Beautiful 360 views!
10.0 out of 10, Exceptional, (167)
"The little blue cottage is so cute sitting alongside the big red brick house. We were in the area to participate in an event. We found this location to be perfectly situated near the event as well as to Shenandoah National Park. The host/hostess made us feel like they really enjoy having guests. We need to come back for the Caverns and fall leaves. "
Beautiful 360 views!
The Carriage House at Carrot Top Cottage
9.8 out of 10, Exceptional, (26)
"Quaint, private, quiet, romantic. Had a warm, romantic feeling. It’s just the right amount of space with a great couch and comfortable bed for two. There is a common area with a fire pit, which was delightful. We had deer In our backyard in the evenings and several other wildlife. It would have been perfect if we had access to a grill. Excellent communication with the owners! The town shuts down early in the evening limiting dinner choices. However 15 minutes away there is access to numerous...
The price is AED 386
AED 649 total
includes taxes & fees
1 Oct - 2 Oct
The Carriage House at Carrot Top Cottage
Cozy retreat near Old Rag
9.8 out of 10, Exceptional, (28)
"I came for dark skies and was not disappointed. Jerry is a great host and the farmhouse was cool and comfortable during a real hot spell. "
Cozy retreat near Old Rag
Historical cottage in the town of Paris
9.8 out of 10, Exceptional, (33)
"What a quaint getaway! Charming little borough in a clean, comfortable cottage! Loved every minute spent there!"
The price is AED 621
AED 1,119 total
includes taxes & fees
13 Oct - 14 Oct
Historical cottage in the town of Paris
Peaceful Lakefront Cottage with Mountain Views!
10.0 out of 10, Exceptional, (20)
"Stayed here for a girls getaway. House was beautiful and the view was so tranquil and beautiful overlooking the lake. The decor was fresh and modern as were the appliances. Well stocked and beautiful kitchen. We enjoyed a very relaxing time. The communication from Mountain Mama was exceptional. "
The price is AED 1,021
AED 2,259 total
includes taxes & fees
6 Oct - 7 Oct
Peaceful Lakefront Cottage with Mountain Views!
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
10.0 out of 10, Exceptional, (12)
"Bed in main room seemed to be broken on left side. Sloping down. Otherwise everything was great "
The price is AED 1,208
AED 1,570 total
includes taxes & fees
29 Sep - 30 Sep
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Hunt Country cottage in Upperville!
9.8 out of 10, Exceptional, (7)
"The owner Constance is wonderful and very responsive. Beautiful home."
Hunt Country cottage in Upperville!
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
10.0 out of 10, Exceptional, (3)
"Thursday afternoon I was looking for a weekend getaway place in the mountains for a 2 night stay on vrbo. This listing was love at first sight. I had couple of questions and quickly messaged the host , who replied back within minutes and that responsiveness was consistent until and after we checked out. Drive up: beautiful and the last 25 minutes was a winding road with beautiful views. The last half mile was gravelly. I would recommend driving in daylight. Checking in: very smooth. Simply...
The price is AED 650
AED 1,565 total
includes taxes & fees
29 Sep - 30 Sep
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Bear Chase Cottage
10.0 out of 10, Exceptional, (28)
"The Bear Chase Cottage is an ideal spot to stay! The area is beautiful and it's perfect if you want to spend the day at the Bear Chase Brewery and walk 30 seconds home. The house is cute, comfortable and completely updated. We'll definitely be back!"
Bear Chase Cottage
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
8.6 out of 10, Excellent, (4)
"The inside of the cottage was very clean. The bathroom towels are like blankets! SO nice! The kitchen is decent (with a little coffee/tea bar and fresh eggs in the refrigerator!!), the living room is spacious and the beds are very comfortable. My only issue with the interior was there was no place to put the luggage in the bedrooms. I had to put my suitcase on the floor and kept having to bend down to get things out of it. It would be nice to have a luggage rack or a small dresser in each room....
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Lost River WV-Relaxing 3brm/2bath farmhouse-dog friendly- large treetop deck
9.8 out of 10, Exceptional, (51)
"The listing I read stated jetted tub & hot tub but no hot tub. Prickly plant coming up from underneath side porch - lights going up the stairs outside only one works - no pen to put comments in book. Overall a quiet weekend."
Lost River WV-Relaxing 3brm/2bath farmhouse-dog friendly- large treetop deck
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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 Mountain Home Features Breathtaking Valley Views and Hot Tub
10.0 out of 10, Exceptional, (349)
"This property is amazing! LOVED the location (don't mind the driveway), loved the house, property, hot tub, fire pit. It was a perfect getaway. We will be back!!! Owners were very easy to work with and provided everything that we needed. Thank you!!!"
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Dreamtime - Modern A-frame Cabin w/ Hot tub
10.0 out of 10, Exceptional, (31)
"Super clean and very comfortable for the two of us. Easy to get to restaurants and very close to a humble, but great brew pub. A couple of other houses nearby but they are hidden by the woods so the house feels very private. The deck and the hot tub are fantastic. Super quick responses from the host. Overall, exactly what we were hoping to find. "
The price is AED 1,098
AED 1,397 total
includes taxes & fees
10 Oct - 11 Oct
Dreamtime - Modern A-frame Cabin w/ Hot tub
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
9.8 out of 10, Exceptional, (281)
"Once again…. a wonderful, peaceful time! We brought our dog with us this time and he had a blast! Toured some wineries and just a short drive for some amazing food. Coffee on the porch and outside fires at night are the best. Already booked next year to come back with friends! "
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
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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