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Featured Cottages in Winchester

Secluded, Cozy Cottage in the Shenandoah Valley
10.0 out of 10, Exceptional, (144)
"Stayed here for a weekend for a mini honeymoon/wife’s birthday. The cabin had everything we needed and more. We stay at a lot of cabins around shenendoah valley and this one was definitely high on the list of quality. Very clean and cozy. We took a hike, enjoyed the fire pit and hot tub, grilled, and relaxed on the upper deck. All the appliances worked and shower was great. Our only issue was the bed was very noisy and sounded like it could use some attention or an upgrade, there was a good...
Secluded, Cozy Cottage in the Shenandoah Valley
Exterior
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (16)
"We had a nice stay in a lovely rural location with nice outdoor terrace and quiet street for a long walk. Communication with the host was simple and straight forward."
The price is NZ$640
per night
9 Jun - 10 Jun
18th Century Stone Cottage minutes from historic Middleburg
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, (6)
"This cottage is adorable! I stayed with my teenage daughter and my mother on a Luckett’s Spring Market trip. Location was less than 20 to the Clarke County Ruritan Fairgrounds. Had dinner at More Better and stopped in to see the view at Bear Claw. Cottage is clean, quaint, and has everything you need. Would stay again and would recommend. Communication w owner was timely and informative. And she went the extra mile with a forgotten item. All around an excellent experience."
The price is NZ$637
per night
23 May - 24 May
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
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Property grounds
Beautiful 360 views!
10.0 out of 10, Exceptional, (155)
"Super quaint little cottage, exactly what we needed. The hosts are incredibly sweet and accommodating. The view is of open farmland with mountians in the distance. The sun sets off the back of the cottage and theres a wonderful view. Really wonderful spot!"
Beautiful 360 views!
Exterior
Our Cottage is in Historical Luray, Walking Distance of Town Restaurants & Shops
10.0 out of 10, Exceptional, (214)
"Nice stay good location"
Our Cottage is in Historical Luray, Walking Distance of Town Restaurants & Shops
Fridge, microwave, oven, stovetop
Peaceful Lakefront Cottage with Mountain Views!
10.0 out of 10, Exceptional, (16)
"It was a lovely way to spend our honeymoon I loved it so much will book again with family"
The price is NZ$1,134
per night
12 Jun - 13 Jun
Peaceful Lakefront Cottage with Mountain Views!
Fridge, microwave, oven, stovetop
Welcome to the “old town cottage”
10.0 out of 10, Exceptional, (52)
"We stayed here when in Warrenton to care for a loved one. It was the perfect location between the hospital and town in a lovely quiet neighborhood. House was very clean and had all the amenities we needed. Chase was wonderful to work with and Mike (the owner) was very welcoming. Not only were we given bread, eggs, sausage at the beginning of our stay, we found some beautiful daffodils on our doorstep during our stay. We will definitely be back! Thank you!"
Welcome to the “old town cottage”
Fridge, microwave, oven, stovetop
Bear Chase Cottage
10.0 out of 10, Exceptional, (25)
"Loved our stay at the cottage! We got take out from the brewery one night and cooked all other meals during our 3 night stay with another couple. Kitchen had everything we needed. Also enjoyed the grill, fire pit and comfortable beds and living area! Loved the proximity to great trails and enjoyed beautiful views and beer at the brewery. Hope to return!"
Bear Chase Cottage
Beach
LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!
10.0 out of 10, Exceptional, (151)
"Check-in was a breeze. The heat was on when we got there, fresh towels, linen, and a fully equipped kitchen. We had everything we needed to cook. We enjoyed using the outdoor charcoal grill for our New Years Eve feast. Our dog loved sniffing around and going down to the river. I wish it would have been warm enough to sit on the screened in porch, it was lovely! Very cozy, we will be back to enjoy it in the warmer months!"
LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!
Exterior
Cottage at Gray Fox- Many Attraction- Pet Friendly
10.0 out of 10, Exceptional, (16)
"We needed a b&b for an out of town wedding and this home could not have been more perfect! The hot tub and gaming system were a huge hit and the beds were beyond comfortable. The hosts were also very responsive and flexible! Highly recommend"
Cottage at Gray Fox- Many Attraction- Pet Friendly
Pool
Cottage w/ Hot Tub and 100-Mile Valley Views!
10.0 out of 10, Exceptional, (11)
"We loved this place! It had everything we needed and everything was very comfortable. The sunset view from the hot tub was a highlight! We would stay here again."
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor dining
Historic Schoolhouse on Winery Row
10.0 out of 10, Exceptional, (5)
"Perfect location for our long weekend. Well equipped & maintained cottage. Hope to return soon."
Historic Schoolhouse on Winery Row
Fridge, microwave, oven, stovetop
The Getaway Cottage at Rocky Marsh Farm
10.0 out of 10, Exceptional, (16)
"Great spot! Spent the weekend with three girlfriends and had a blast. The home was spotless, cozy, modern, and with a very well-equipped kitchen. Beautiful, bright windows, excellent views, and warm, inviting decor. Owners were responsive but not intrusive; we had no issues during our stay. I can't wait to come back!"
The Getaway Cottage at Rocky Marsh Farm
Property grounds
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
10.0 out of 10, Exceptional, (12)
"Very clean! The outdoor space is amazing and better than photos. Host was super responsive to texting. Wish we would have planned an extra day to just enjoy the house and property more!"
The price is NZ$1,076
per night
23 May - 24 May
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
2 bedrooms, iron/ironing board, WiFi, bed sheets
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
10.0 out of 10, Exceptional, (2)
"Can’t wait to go back."
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Exterior
Alpacas & The Stars at night. Private Retreat. Fun & Peace
10.0 out of 10, Exceptional, (42)
"Very nice place to stay that is generally convenient to several towns and eating places. Hosts were very nice and helpful and we enjoyed getting to know them and their animals. Look forward to returning."
Alpacas & The Stars at night. Private Retreat. Fun & Peace
Exterior
Historical cottage in the town of Paris
9.8 out of 10, Exceptional, (20)
"We were very happy with our stay at this cottage. We're always looking for historic houses to stay in on our trips and this one did not disappoint. We loved sitting by the fire at night and enjoyed the screened-in porch on the rainy mornings. The neighborhood was nice and quiet. We would definitely stay here again."
The price is NZ$499
per night
30 May - 31 May
Historical cottage in the town of Paris
Interior
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
9.8 out of 10, Exceptional, (28)
"Well kept home, everything you need in the kitchen, close to the Caverns. The host were wonderful, replied to any messages I sent very fast, only thing I would change about this house would be a blind or curtain in kitchen window and covering over the front glass door but that wouldn't stop me from renting this home again if I was to return to the area. Thanks for making my stay a wonderful one!"
The price is NZ$518
per night
23 May - 24 May
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Property grounds
Lost River Swiss Cottage/10 acres/Private Dog Park/Streams
9.8 out of 10, Exceptional, (117)
"The house has been updated nicely especially bathrooms! Great view and the screened in porch is amazing! The location is fantastic, close to The Guesthouse and the farmer's s market too! If you are planning to cook a lot as we did, there is not a ton of counter space and no dishwasher."
Lost River Swiss Cottage/10 acres/Private Dog Park/Streams
Fridge, microwave, oven, stovetop
Cozy retreat near Old Rag
9.8 out of 10, Exceptional, (26)
"Comfortable, clean and peaceful! Cottage is a perfect place to stay while exploring the area. Jerry is one of the best hosts I have encountered, very thoughtful but respectful of privacy. He is available to help with suggestions to ensure you have the best trip possible. Would definitely recommend Jerry's place to anyone coming to the area and/or wanting to hike Old Rag!"
Cozy retreat near Old Rag
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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.

Other property types in Winchester

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (142)
"We really enjoyed the secluded location. It felt just far enough away but also easy to get to the cities nearby. We had a few issues with bugs, but nothing unexpected for mountain life. The kitchen was well stocked and the wifi worked surprisingly well during our stay. This was great for our girls trip and we would definitely come here again!"
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Property grounds
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
9.6 out of 10, Exceptional, (151)
"We enjoyed the home but the land even more. Nature is awesome!"
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
Garden
Family Farmhouse Inn
3.0 star property
9.6 out of 10, Exceptional, (25)
"excellent "
The price is NZ$224
per night
28 May - 29 May
Family Farmhouse Inn
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.

Winchester Cottages information

Number of reviews
1,110
Accommodation
153 Cottages
Lowest Price
NZ$351
Highest Price
NZ$1,134

Recent Reviews in Winchester
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