Winchester Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winchester vacation rentals

A modern living room with a sofa, a coffee table, and a lamp. There is a kitchen area in the background with cabinets and a painting on the wall.

1. Executive Suites

Executive Suites
3.0 star property
Winchester
The price is AED 927
AED 1,050 total
includes taxes & fees
13 Nov - 14 Nov
Executive Suites
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

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."
United States
Timothy B.
The price is AED 544
AED 911 total
includes taxes & fees
19 Nov - 20 Nov
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A living room with a sofa, ottoman, lamp, and a mirror.

3. Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is AED 588
AED 1,016 total
includes taxes & fees
15 Nov - 16 Nov
Morocco Loft 2BR overlooking city walking mall
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

4. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester 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"
United States
Jameson D.
The price is AED 404
AED 649 total
includes taxes & fees
15 Nov - 16 Nov
Rosamond nice downtown studio apt
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

5. The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
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."
United States
Chris C.
The price is AED 275
AED 894 total
includes taxes & fees
16 Nov - 17 Nov
The Queen of Winchester Three Bedroom with Upper Level Deck
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

6. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester 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!"
United States
Leslie L.
The price is AED 507
AED 791 total
includes taxes & fees
15 Nov - 16 Nov
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A two-story house with a front porch, a mailbox, and a number plate.

7. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
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."
United States
Carolyn F.
The price is AED 727
AED 1,178 total
includes taxes & fees
15 Nov - 16 Nov
Cameron Charmer pristine downtown apt with double master suites
A hot tub in front of a wooden cabin with a tree in the background.

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 City
Stephens 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! "
United States
Laura H.
The price is AED 533
AED 642 total
includes taxes & fees
16 Nov - 17 Nov
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A living room with a sofa, armchair, coffee table, and a television.

9. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.0 out of 10, Wonderful, (22 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
The price is AED 680
AED 1,124 total
includes taxes & fees
15 Nov - 16 Nov
Nostalgia Lane in the heart of the city
A modern, dark-colored triangular building with a balcony and outdoor seating area.

10. Chalet w/Hot Tub, Deck, Game Room & EV Charger

Chalet w/Hot Tub, Deck, Game Room & EV Charger
Stephens 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!"
United States
Laura V.
The price is AED 714
AED 1,414 total
includes taxes & fees
30 Nov - 1 Dec
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A building with a red door, white trim, and a small balcony with a metal railing.

11. The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
United States
Greg A.
The price is AED 404
AED 670 total
includes taxes & fees
15 Nov - 16 Nov
The Stock Exchange downtown 3rd floor studio apt
A wooden deck with white railings and a covered porch area.

12. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (51 reviews)
"It was great and beautiful place to staying. Thanks for hospitality"
United States
Onon
The price is AED 496
AED 752 total
includes taxes & fees
22 Nov - 23 Nov
Mountain View Bungalow in Front Royal
A house with a fire pit in the foreground and a deck with string lights in the background.

13. 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 6
Strasburg
10.0 out of 10, Exceptional, (20 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!"
United States
Paul S.
The price is AED 790
AED 1,766 total
includes taxes & fees
16 Nov - 17 Nov
The Haven at Turkey Run | Hot Tub, Creek + Disc Golf on 13 Acres | 3BR, Sleeps 6
A hot tub area with a wooden structure overhead, a bottle, and glasses.

14. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.4 out of 10, Exceptional, (40 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
The price is AED 1,211
AED 2,433 total
includes taxes & fees
23 Nov - 24 Nov
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

15. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front 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!"
United States
Hailey
The price is AED 1,074
AED 1,519 total
includes taxes & fees
15 Nov - 16 Nov
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A hot tub with a view of a forest and a sunset.

16. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.6 out of 10, Exceptional, (14 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
The price is AED 486
AED 1,237 total
includes taxes & fees
19 Nov - 20 Nov
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A spacious living room with a fireplace, a dining area with a bench, and a large sliding glass door leading to an outdoor patio.

17. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.6 out of 10, Exceptional, (9 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
The price is AED 514
AED 1,353 total
includes taxes & fees
15 Nov - 16 Nov
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A covered outdoor area with a fire pit, seating, and a view of the landscape.

18. Mountaintop Cottage | Private Hot Tub

Mountaintop Cottage | Private Hot Tub
Front 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."
United States
Kevin D.
The price is AED 1,143
AED 2,227 total
includes taxes & fees
18 Nov - 19 Nov
Mountaintop Cottage | Private Hot Tub
A lakeside property with a dock, a wooden deck, and a house surrounded by dense greenery.

19. Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6

Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
Front Royal
9.4 out of 10, Exceptional, (3 reviews)
"The gravel road to get to the properly is an adventure. The owner described it perfectly."
United States
Denise A.
The price is AED 494
AED 1,416 total
includes taxes & fees
15 Nov - 16 Nov
Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
A hot tub on an outdoor deck with a view of trees and hills.

20. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | Hot Tub & Game Room
Front Royal
9.8 out of 10, Exceptional, (17 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is AED 1,349
AED 2,458 total
includes taxes & fees
15 Nov - 16 Nov
Mountain View Cottage | Hot Tub & Game Room
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.
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Top Winchester Hotel Reviews

A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
Huntly

10/10 Excellent

Perfect
United States
Omar
Reviewed June 16, 2026
Glen Gordon Manor

Frequently Asked Questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals in Winchester near Shenandoah Valley Discovery Museum, or you can go with a secluded option if you want a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theater scene while you're visiting.

What are some of the best vacation home rentals in Winchester?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This vacation home near Winchester is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Winchester?

Choose from 15 Expedia vacation rentals in Winchester for a memorable vacation.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of family-friendly sights, whereas cultural attractions include Bright Box Theater and Museum of the Shenandoah Valley. Other places in town to visit include Patsy Cline Historic House and Apple Blossom Mall.

What’s a vacation rental in Winchester like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winchester. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for family trips.