Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for Winchester vacation rentals
1. Executive Suites
Executive SuitesWinchester
$252 nightly
The price is $286
Nov 9 - Nov 10
Total with taxes and fees
2. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
Timothy B.
$213 nightly
The price is $241
Nov 19 - Nov 20
Total with taxes and fees
3. Rosamond nice downtown studio apt
Rosamond nice downtown studio aptWinchester Historic District
8.8 out of 10, Excellent, (3 reviews)
"Easy space for a 2 person weekend getaway, very close within walking distance to food, shops, breweries, etc"
Jameson D.
$158 nightly
The price is $179
Nov 12 - Nov 13
Total with taxes and fees
4. The Queen of Winchester Three Bedroom with Upper Level Deck
The Queen of Winchester Three Bedroom with Upper Level DeckWinchester
7.6 out of 10, Good, (8 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
Chris C.
$221 nightly
The price is $228
Nov 30 - Dec 1
Total with taxes and fees
5. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mallWinchester Historic District
8.4 out of 10, Very good, (6 reviews)
"Loved being so close to the old town; was able to walk to a lot of places. Great to have an assigned parking spot in a lot behind the building. Enjoyed staying here a lot!"
Leslie L.
$192 nightly
The price is $218
Nov 15 - Nov 16
Total with taxes and fees
6. Morocco Loft 2BR overlooking city walking mall
Morocco Loft 2BR overlooking city walking mallOld Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Great property with all the comforts of home"
Kristen R.
$265 nightly
The price is $300
Nov 15 - Nov 16
Total with taxes and fees
7. Cameron Charmer pristine downtown apt with double master suites
Cameron Charmer pristine downtown apt with double master suitesWinchester
9.8 out of 10, Exceptional, (11 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
Carolyn F.
$286 nightly
The price is $324
Nov 9 - Nov 10
Total with taxes and fees
8. Luxury tiny home farm stay on historic property with hot tub in Stephens City
Luxury tiny home farm stay on historic property with hot tub in Stephens CityStephens City
10.0 out of 10, Exceptional, (15 reviews)
"This tiny house was an absolute dream to stay at! Jen is very attentive to detail- everything from the decor to the thoughtful welcome basket and supplying a feed bucket for the farm animals was perfection. My kids requested our next vacation just be there instead! "
Laura H.
$153 nightly
The price is $170
Nov 16 - Nov 17
Total with taxes and fees
9. The Stock Exchange downtown 3rd floor studio apt
The Stock Exchange downtown 3rd floor studio aptWinchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
Greg A.
$163 nightly
The price is $185
Nov 12 - Nov 13
Total with taxes and fees
10. Mountain View Bungalow in Front Royal
Mountain View Bungalow in Front RoyalFront Royal
10.0 out of 10, Exceptional, (50 reviews)
"Very cute and clean home. The location was great and Vanessa was awesome to work with"
Diedra
$184 nightly
The price is $205
Nov 9 - Nov 10
Total with taxes and fees
11. Nostalgia Lane in the heart of the city
Nostalgia Lane in the heart of the cityOld Town Winchester
8.8 out of 10, Excellent, (21 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
Melissa J.
$273 nightly
The price is $309
Nov 9 - Nov 10
Total with taxes and fees
12. Chalet w/Hot Tub, Deck, Game Room & EV Charger
Chalet w/Hot Tub, Deck, Game Room & EV ChargerStephens City
10.0 out of 10, Exceptional, (11 reviews)
"A wonderful place to relax and enjoy being with family or friends, with lots of room for the dogs to run and play!"
Laura V.
$338 nightly
The price is $371
Nov 30 - Dec 1
Total with taxes and fees
13. Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6Front Royal
10.0 out of 10, Exceptional, (2 reviews)
"The gravel road to get to the properly is an adventure. The owner described it perfectly."
Denise A.
$340 nightly
The price is $375
Nov 9 - Nov 10
Total with taxes and fees
14. 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.
$186 nightly
The price is $205
Nov 9 - Nov 10
Total with taxes and fees
15. Newly renovated Farm cottage with Mountain views
Newly renovated Farm cottage with Mountain viewsStrasburg
10.0 out of 10, Exceptional, (57 reviews)
"We enjoyed our stay here. The property was lovely and the house was nicely stocked and decorated. We will definitely stay again when in the area!"
Marsha N.
$274 nightly
The price is $302
Nov 29 - Nov 30
Total with taxes and fees
16. The Haven at Turkey Run | Hot Tub, Creek + Disc Golf on 13 Acres | 3BR, Sleeps 6
The Haven at Turkey Run | Hot Tub, Creek + Disc Golf on 13 Acres | 3BR, Sleeps 6Strasburg
10.0 out of 10, Exceptional, (19 reviews)
"This was the ideal isolated cabin for our trip to Northern Virginia. It was clean, well laid out, and very well stocked with everything you need. I highly recommend staying here if you are in the area!"
Paul S.
$426 nightly
The price is $470
Nov 9 - Nov 10
Total with taxes and fees
17. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
The Honeymoon Cabin | Private Couple's Retreat w/ hot tubFront Royal
9.6 out of 10, Exceptional, (8 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
P H.
$321 nightly
The price is $354
Nov 15 - Nov 16
Total with taxes and fees
18. Blue Mountain Cabin, secluded, perfect for couples, near main road
Blue Mountain Cabin, secluded, perfect for couples, near main roadFront Royal
10.0 out of 10, Exceptional, (47 reviews)
"Nice cabin for couples. The bed was comfy and had all basic necessities for making meals. We will definitely stay again."
Carla M.
$218 nightly
The price is $240
Nov 9 - Nov 10
Total with taxes and fees
19. Cozy A frame cabin in quaint Front Royal. Dog friendly
Cozy A frame cabin in quaint Front Royal. Dog friendlyFront Royal
9.4 out of 10, Exceptional, (11 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
Kye Y.
$233 nightly
The price is $257
Nov 11 - Nov 12
Total with taxes and fees
20. NEW! Greek Spa - Frisbee Golf - Stonefire Pizza
NEW! Greek Spa - Frisbee Golf - Stonefire PizzaFront Royal
$263 nightly
The price is $264
Nov 16 - Nov 17
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.
Top Winchester Hotel Reviews
Glen Gordon Manor
Glen Gordon ManorHuntly
10/10 Excellent
Perfect
Omar
