A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Winchester Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Winchester holiday rentals

Private kitchen

1. 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 Queen of Winchester Three Bedroom with Upper Level Deck
Interior

2. Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.6 out of 10, Exceptional, (9 reviews)
"Perfect location for walking around Old Town Winchester!"
United States
Clint B.
Pretty Little Apt by the Train II
Interior

3. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is HK$863
HK$1,519 total
includes taxes & fees
24 Sept - 25 Sept
Rosamond nice downtown studio apt
Living area

4. 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
10.0 out of 10, Exceptional, (2 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 HK$1,161
HK$2,052 total
includes taxes & fees
24 Sept - 25 Sept
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Living area

5. 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 HK$1,082
HK$1,848 total
includes taxes & fees
17 Sept - 18 Sept
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Exterior detail

6. 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 Stock Exchange downtown 3rd floor studio apt
Terrace/patio

7. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (38 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is HK$1,059
HK$1,737 total
includes taxes & fees
16 Sept - 17 Sept
Mountain View Bungalow in Front Royal
Exterior detail

8. The Blue Door steps from Handley Library

The Blue Door steps from Handley Library
Old Town Winchester
5.4 out of 10, (3 reviews)
"Perfect. Met all expectations. Small but Great."
United States
derric3k
The Blue Door steps from Handley Library
Terrace/patio

9. 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, (13 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
The price is HK$1,137
HK$1,440 total
includes taxes & fees
5 Oct - 6 Oct
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Private kitchen

10. Buena Vista

Buena Vista
Shawneeland
10.0 out of 10, Exceptional, (1 review)
The price is HK$753
HK$1,773 total
includes taxes & fees
23 Sept - 24 Sept
Buena Vista
Living area

11. 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 HK$1,396
HK$2,559 total
includes taxes & fees
24 Sept - 25 Sept
Morocco Loft 2BR overlooking city walking mall
Private kitchen

12. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Old Town Winchester
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is HK$1,529
HK$1,981 total
includes taxes & fees
13 Sept - 14 Sept
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Living area

13. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.2 out of 10, Wonderful, (18 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 HK$1,451
HK$2,621 total
includes taxes & fees
15 Sept - 16 Sept
Nostalgia Lane in the heart of the city
Exterior

14. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.6 out of 10, Exceptional, (9 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 HK$1,553
HK$2,683 total
includes taxes & fees
13 Sept - 14 Sept
Cameron Charmer pristine downtown apt with double master suites
Outdoor spa tub

15. 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
9.4 out of 10, Exceptional, (13 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 HK$1,108
HK$2,865 total
includes taxes & fees
23 Sept - 24 Sept
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Terrace/patio

16. Peaceful mountain cabin in charming Berryville VA - next to river and brewery

Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Berryville
10.0 out of 10, Exceptional, (3 reviews)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveller
The price is HK$588
HK$1,920 total
includes taxes & fees
5 Oct - 6 Oct
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Exterior

17. Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
The price is HK$1,466
HK$2,474 total
includes taxes & fees
20 Sept - 21 Sept
Cozy A frame cabin in quaint Front Royal. Dog friendly
Indoor spa tub

18. The Foxwood Cabin | Hot Tub, Screened Porch, Grill

The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"Excellent stay. Very quiet and private. The property was very clean, had all of the amenities needed. Very comfortable and homey. The only thing you need to be aware of is that the USPS does not deliver to the address, Amazon will have the post office hold it in Front Royal."
United States
Roland C.
The price is HK$1,231
HK$3,693 total
includes taxes & fees
7 Oct - 8 Oct
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Dining

19. WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Old Town Winchester
9.0 out of 10, Wonderful, (10 reviews)
"Great location…"
United States
John P.
The price is HK$1,608
HK$2,932 total
includes taxes & fees
24 Sept - 25 Sept
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Living area

20. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.6 out of 10, Exceptional, (8 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is HK$1,741
HK$3,101 total
includes taxes & fees
20 Sept - 21 Sept
Scarborough Fair walk to downtown two story apt
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

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"Highly recommend"
Mary 1-night trip
Posted less than an hour ago
Fairfield Inn & Suites by Marriott Winchester

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting.

What are some of the best holiday rentals that Winchester has to offer?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This holiday home rental outside of Winchester is located in a rural location, and has a fireplace, a balcony and a BBQ 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 holiday with amenities such as a selection of games.

How many holiday rentals will I find in Winchester?

Choose from 14 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

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

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.