Search Winchester Cottages

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 153 Cottages in Winchester with updated reviews, rates, and availability.

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
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
$300 total
includes taxes & fees
May 28 - May 29
Historical cottage in the town of Paris
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 $270
$391 total
includes taxes & fees
Jun 9 - Jun 10
18th Century Stone Cottage minutes from historic Middleburg
Save an average of 15% on thousands of hotels when you're signed in
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 $160
$315 total
includes taxes & fees
May 22 - May 23
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
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)
"All good"
The price is $299
$389 total
includes taxes & fees
May 22 - May 23
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
View from property
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, (104)
"Sweet place! We brought out dog, and it felt like a second home - safe, beautiful, and easy."
RIVERKEEPER INN, Waterfront Property on the Potomac River
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)
"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
Exterior
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
$215 total
includes taxes & fees
May 27 - May 28
Cozy Cottage
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 $333
$692 total
includes taxes & fees
Jun 12 - Jun 13
Peaceful Lakefront Cottage with 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
Aerial view
Peaceful Waterfall House -- 2 bedroom hidden treasure
The price is $223
$345 total
includes taxes & fees
May 22 - May 23
Peaceful Waterfall House -- 2 bedroom hidden treasure
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
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
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
Property grounds
3brm/2bath Mntside Farmhouse-dog friendly
9.8 out of 10, Exceptional, (49)
"Karen's rental is an adorable home in the country. The kitchen is wonderfully stocked, and the fenced in yard is fantastic for anyone travelling with dogs! Karen is also a very responsive, helpful host. If you want to have a lovely remote retreat, this is the place to stay."
3brm/2bath Mntside Farmhouse-dog friendly
Exterior
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!
Exterior
Carrot Top Cottage surrounded by National Park
9.8 out of 10, Exceptional, (20)
"Would definitely stay again and highly recommend!"
Carrot Top Cottage surrounded by National Park
Don't see what you're looking for?
See all available properties in Winchester
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)
"The property was exactly as described. The house was lovely and well appointed. our friends and I had a wonderful time."
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 $120
$135 total
includes taxes & fees
Jun 10 - Jun 11
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
1,109
Accommodation
153 Cottages
Lowest Price
$94
Highest Price
$333

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?
With Expedia’s filter tool, comparing cheap cottages in Winchester is a snap. To view properties that’ll make your hip pocket happy, narrow your search by star rating, amenities and budget.
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.

Recent reviews of Winchester hotels
Expedia verified reviews