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

Beautiful 360 views!
10.0 out of 10, Exceptional, (156)
"We really enjoyed our stay at the property- it was comfortable, clean, and quiet- everything we needed. The hosts were kind and helpful. I loved the breakfast bar that looked out over a beautiful view."
Beautiful 360 views!
Secluded, Cozy Cottage in the Shenandoah Valley
10.0 out of 10, Exceptional, (145)
"My husband and I stayed for the weekend. While the home is definitely out in the woods, it is not as secluded as we had hoped. There is a large occupied house that looks down on the rental house and hot tub. The ring doorbell can also see the hot tub, and we did not feel like it was private enough for us to use. The house is beautiful and there is plenty of space to wander in the woods."
Secluded, Cozy Cottage in the Shenandoah Valley
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, (104)
"We had a wonderful time, even in the rain! Easy river access and beautiful views of both the water and green spaces."
RIVERKEEPER INN, Waterfront Property on the Potomac River
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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 $270
$391 total
includes taxes & fees
Jun 9 - Jun 10
18th Century Stone Cottage minutes from historic Middleburg
Cozy Cottage
9.2 out of 10, Wonderful, (18)
"Cottage is quaint, with modern design. Perfect for my husband and I and our pup. Very clean, with tasteful decor. Within walking distance to town. Had everything you need."
The price is $94
$216 total
includes taxes & fees
Jun 10 - Jun 11
Cozy Cottage
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
9.8 out of 10, Exceptional, (30)
"Comfortable place to stay while we passed through the area to do some hiking. Clean and nice amenities for the short stay. There were indications of a hot tub in the listing, but there isn’t one. I would recommend some type of curtain on the front door glass it gives a pretty full view of the inside at night."
The price is $170
$329 total
includes taxes & fees
Jun 11 - Jun 12
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Lost River Swiss Cottage/10 acres/Private Dog Park/Streams
9.8 out of 10, Exceptional, (118)
"Had a wonderful long weekend with family at this wonderful mountain cottage. The house was incredibly clean, updated bathrooms, comfortable beds, and attention to small details like light fixtures and bedding. The location was pretty and within walking distance to the Saturday Farmers Market. The real star of this house is the large screened in porch with scenic views and a breeze. It was the perfect spot for morning coffee and evening happy hour. We did not even care when it rained a bit and...
Lost River Swiss Cottage/10 acres/Private Dog Park/Streams
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
10.0 out of 10, Exceptional, (7)
"casual, cozy and convenient to the brewery. great views and enjoyed the hot tub"
The price is $330
$429 total
includes taxes & fees
Jun 10 - Jun 11
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
Peaceful Waterfall House -- 2 bedroom hidden treasure
The price is $223
$345 total
includes taxes & fees
Jun 9 - Jun 10
Peaceful Waterfall House -- 2 bedroom hidden treasure
Woodsy Retreat with a Hot Tub and Seasonal Views!
10.0 out of 10, Exceptional, (10)
"The cabin was great. Clean, well stocked, and quite. It was just what we needed for a long weekend away from everything. Can't wait to do it again."
Woodsy Retreat with a Hot Tub and Seasonal Views!
Mountain Royal at the Woods Resort
9.2 out of 10, Wonderful, (5)
"We love this house and it is so cozy. We had great time w family and enjoyed every moment"
Mountain Royal at the Woods Resort
Our Cottage is in Historical Luray, Walking Distance of Town Restaurants & Shops
10.0 out of 10, Exceptional, (214)
"It was a lovely home that was equipped with everything you need. Highly recommended."
Our Cottage is in Historical Luray, Walking Distance of Town Restaurants & Shops
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
10.0 out of 10, Exceptional, (3)
"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.
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 $169
$305 total
includes taxes & fees
Jul 1 - Jul 2
Historical cottage in the town of Paris
LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!
10.0 out of 10, Exceptional, (151)
"What an amazing spot on the river! This place was so amazing with absolutely beautiful view of the river, my city wife was so awestruck by this place she immediately started searching for a place for sale in the general area. I got a very strong feeling we’ll be doing another stay at this awesome place later this year."
LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!
The Carriage House at Carrot Top Cottage
9.6 out of 10, Exceptional, (17)
"Perfect location for visiting Harpers Ferry and Charles Town"
The Carriage House at Carrot Top Cottage
Cozy Retreat - Hot tub + Mountain Views + Pets
10.0 out of 10, Exceptional, (9)
"Everything was just as it should be when one is seeking a “retreat.” Cozy, cheerful, immaculate. The host has really paid attention to all the details. There wasn’t one thing we needed or wanted that was missing. Terrific beds, bedding and pillows. Great coffee. Well organized and equipped kitchen. Extremely clear communication. And the drive from one end of Fort Valley to the other is a memory we will always cherish!"
The price is $93
$273 total
includes taxes & fees
Jun 9 - Jun 10
Cozy Retreat - Hot tub + Mountain Views + Pets
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”
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
Riversong Luxe Cabin w/ Fire Pit on North River
3.0 star property
Riversong Luxe Cabin w/ Fire Pit on North River
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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, (189)
"My family and I stayed with our dog at this beautiful cabin. It was spacious and decorated so nicely. Very cozy and relaxing atmosphere! We will definitely be back."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Dreamtime - Modern A-frame Cabin w/ Hot tub
10.0 out of 10, Exceptional, (26)
"Cabin was amazing. Definitely would go back!"
The price is $375
$471 total
includes taxes & fees
Jul 6 - Jul 7
Dreamtime - Modern A-frame Cabin w/ Hot tub
Hidden Gem in the woods with hot tub
9.6 out of 10, Exceptional, (50)
"We had a great time. Cabin was clean, spacious and well maintained. The fire pit and hot tub were what we looked forward to the most... We were not disappointed."
Hidden Gem in the woods with 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.

Winchester Cottages information

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Frequently asked questions

Why book your cottage in Winchester with Expedia?
Expedia has some terrific cottages in Winchester, so get set for a memorable vacay close to nature. If you’re sticking to a budget, select how much you’re willing to spend and the preferred star rating of your property. Or, try out our filters to search for cottages with a pool or a kitchen. We’ll help you find the right fit whatever your style of travel or plans.
How can I find cheap cottages in Winchester?
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What is there to do in Winchester near my cottage?
You’ll find loads of wonderful things to fill your itinerary with in Winchester. Head for major attractions like Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theater. Winchester Little Theater, Valerie Hill Winery and Shenandoah University also appeal to many visitors.

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