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Our top choices for Winchester cottages
1. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-FiBoyce
9.4 out of 10, Exceptional, (40 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
Felice N.
$612 nightly
The price is $675
Nov 23 - Nov 24
Total with taxes and fees
2. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain ViewFront Royal
9.0 out of 10, Wonderful, (18 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
Jake M.
$193 nightly
The price is $212
Nov 12 - Nov 13
Total with taxes and fees
3. Mountaintop Cottage | Private Hot Tub
Mountaintop Cottage | Private Hot TubFront Royal
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay, house was beautiful and clean. Coffee in the morning with the deer was awesome. Love the neighborhood cat Luna."
Kevin D.
$547 nightly
The price is $603
Nov 12 - Nov 13
Total with taxes and fees
4. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Riverfront! Shenandoah River! Sleeps 4! New Hot TubFront Royal
9.8 out of 10, Exceptional, (16 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
Hailey
$373 nightly
The price is $415
Nov 12 - Nov 13
Total with taxes and fees
5. Mountain View Cottage | Hot Tub & Game Room
Mountain View Cottage | Hot Tub & Game RoomFront Royal
9.8 out of 10, Exceptional, (17 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
Katia R.
$607 nightly
The price is $669
Nov 15 - Nov 16
Total with taxes and fees
6. Mountain View Cottage with Hot Tub and River Views
Mountain View Cottage with Hot Tub and River ViewsFront Royal
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay and certainly return. Our group was 2 couples and 2 children.Everyone had enough space to be comfortable. The view is beautiful so we enjoyed our time at the house. While in the area, we visited Skyline Caverns and the Shenandoah River. I did have a challenging time getting Door Dash to the house. After 30 minutes of seeing the driver in the neighborhood we got in the car to track down the driver. Her cell service was poor so we were unable to communicate. If I ordered...
MaryBeth C.
$445 nightly
The price is $491
Dec 1 - Dec 2
Total with taxes and fees
7. Quaint Mini Cottage in Shepherdstown - Walking Distance
Quaint Mini Cottage in Shepherdstown - Walking DistanceShepherdstown
9.8 out of 10, Exceptional, (27 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
Abigail
$189 nightly
The price is $211
Nov 15 - Nov 16
Total with taxes and fees
8. Cottage w/ Hot Tub and 100-Mile Valley Views!
Cottage w/ Hot Tub and 100-Mile Valley Views!Harpers Ferry
9.8 out of 10, Exceptional, (29 reviews)
"My husband and I went for a short trip. The communication was great and the house was perfect! We spent most of our time in the hot tub checking out the amazing view."
Keri L.
$406 nightly
The price is $454
Nov 23 - Nov 24
Total with taxes and fees
9. Peaceful Lakefront Cottage with Mountain Views!
Peaceful Lakefront Cottage with Mountain Views!Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"The property was absolutely beautiful. The view of the lake was so pretty. Communication with the host was wonderful very informative. Very cozy and the house was beautiful inside."
Tara G.
$466 nightly
The price is $507
Nov 18 - Nov 19
Total with taxes and fees
10. Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Art Docko - Lakefront Artist Retreat w/ Hot Tub!Harpers Ferry
10.0 out of 10, Exceptional, (29 reviews)
"With bedrooms and sitting rooms on 3 floors, our 3-generation family enjoyed having space to gather together as well as space for time apart. The decks allowed for additional places to enjoy the beautiful surroundings. Lake access was great for swimming and kayaking."
Lindy K.
$512 nightly
The price is $557
Nov 18 - Nov 19
Total with taxes and fees
11. Woodsy Retreat with a Hot Tub and Seasonal Views!
Woodsy Retreat with a Hot Tub and Seasonal Views!Harpers Ferry
9.8 out of 10, Exceptional, (29 reviews)
"Property was a great location for all we wanted to do during our vacation. The beach area was the perfect retreat for some relaxation after long days of hiking. Area is beautiful, house was comfortable (slept like a baby), and we had a great stay. Would definitely stay again."
Rebecca N.
$422 nightly
The price is $460
Nov 12 - Nov 13
Total with taxes and fees
12. Walk to Stores: Home in Historic Shepherdstown!
Walk to Stores: Home in Historic Shepherdstown!Shepherdstown
$335 nightly
The price is $355
Nov 19 - Nov 20
Total with taxes and fees
13. The Carriage House at Carrot Top Cottage
The Carriage House at Carrot Top CottageHarpers Ferry
9.8 out of 10, Exceptional, (55 reviews)
"Very clean and convenient for seeing Harpers Ferry"
Rich C.
$188 nightly
The price is $210
Nov 12 - Nov 13
Total with taxes and fees
14. Round House w Mountain View Hot Tub
Round House w Mountain View Hot TubLuray
10.0 out of 10, Exceptional, (1 review)
$252 nightly
The price is $279
Nov 12 - Nov 13
Total with taxes and fees
15. Cozy Riverfront Cottage, Fire Pit, Pet Friendly
Cozy Riverfront Cottage, Fire Pit, Pet FriendlyRileyville
$307 nightly
The price is $341
Nov 15 - Nov 16
Total with taxes and fees
16. 18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic MiddleburgMiddleburg
10.0 out of 10, Exceptional, (68 reviews)
"A quaint cottage in a beautiful location!"
Mary H.
$366 nightly
The price is $393
Nov 15 - Nov 16
Total with taxes and fees
17. Peaceful Waterfall House -- 2 bedroom hidden treasure
Peaceful Waterfall House -- 2 bedroom hidden treasureBerkeley Springs
9.6 out of 10, Exceptional, (17 reviews)
"We really enjoyed the secluded house surrounded by nature. The waterfall was smaller than we expected, but the sound of it was soothing and we enjoyed tubing in the pond. Our family appreciated the many games in the house and the ice-pops in the freezer."
Dovid J.
$271 nightly
The price is $302
Nov 15 - Nov 16
Total with taxes and fees
18. Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Amazing dog-friendly cottage. Walk 2 Harpers FerryHarpers Ferry
9.8 out of 10, Exceptional, (36 reviews)
"We enjoyed our stay here so much and when we go back to Harper’s Ferry we hope to stay in the same place again"
Zachary S.
$291 nightly
The price is $325
Nov 12 - Nov 13
Total with taxes and fees
19. Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West VirginiaThe Woods
$446 nightly
The price is $498
Nov 15 - Nov 16
Total with taxes and fees
20. Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road Cottage
Mountain Views + Private Hot Tub + Sauna + Game Room - Country Road CottageBerkeley Springs
10.0 out of 10, Exceptional, (5 reviews)
"One of the best properties I’ve rented. Everything was better than described and the description was already stellar. Highly recommend and will likely rent again. "
Cyndi P.
$410 nightly
The price is $457
Nov 29 - Nov 30
Total with taxes and fees
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 and related destinations
Stroll through the charming pedestrian mall in the historic district, where shops and excellent restaurants await. Delve into local culture at the Museum of the Shenandoah Valley or catch a show at the Bright Box Theater.
Top reviews in Winchester
Glen Gordon Manor
Glen Gordon ManorHuntly
10/10 Excellent
Perfect
Omar
