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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winchester holiday rentals

Terrace/patio

1. Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
9.6 out of 10, Exceptional, (8 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveller
The price is HK$784
HK$1,377 total
includes taxes & fees
9 Aug - 10 Aug
Cozy English Basement Apt quiet but close to downtown
Fridge, microwave, oven, stovetop

2. 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 HK$957
HK$2,421 total
includes taxes & fees
10 Aug - 11 Aug
The Queen of Winchester Three Bedroom with Upper Level Deck
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.
Rosamond nice downtown studio apt
Smart TV, books

4. 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
8.8 out of 10, Excellent, (5 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$1,239
HK$2,026 total
includes taxes & fees
4 Sept - 5 Sept
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
TV

5. 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$1,333
HK$2,248 total
includes taxes & fees
4 Sept - 5 Sept
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Interior

6. 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)
"This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again."
United States
Stephanie L.
The price is HK$1,176
HK$1,866 total
includes taxes & fees
4 Sept - 5 Sept
Pretty Little Apt by the Train II
Exterior

7. Entire home in Apple Mountain Lake, Virginia,

Entire home in Apple Mountain Lake, Virginia,
Apple Mountain Lake
The price is HK$1,235
HK$2,453 total
includes taxes & fees
4 Sept - 5 Sept
Entire home in Apple Mountain Lake, Virginia,
Exterior detail

8. 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 HK$1,020
HK$1,733 total
includes taxes & fees
4 Sept - 5 Sept
The Stock Exchange downtown 3rd floor studio apt
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, (11 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
31 Aug - 1 Sept
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Private kitchen

10. 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, (8 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is HK$1,529
HK$1,928 total
includes taxes & fees
4 Sept - 5 Sept
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Exterior

11. 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)
"Nice house in a good central location. "
United States
Mitchell V.
The price is HK$1,553
HK$2,773 total
includes taxes & fees
16 Aug - 17 Aug
Cameron Charmer pristine downtown apt with double master suites
Smart TV

12. 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, (17 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$2,586 total
includes taxes & fees
1 Sept - 2 Sept
Nostalgia Lane in the heart of the city
Smart TV

13. Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4 reviews)
"You need to add some kitchen tongs Otherwise everything was fantastic!!!"
United States
Michelle K.
The price is HK$1,145
HK$2,044 total
includes taxes & fees
13 Aug - 14 Aug
Yellow Submarine trendy basement apt and courtyard
Private kitchen

14. Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Old Town Winchester
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Terrace/patio

15. 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, (1 review)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveller
The price is HK$588
HK$1,687 total
includes taxes & fees
18 Aug - 19 Aug
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Exterior

16. Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA

Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
Front Royal
The price is HK$1,648
HK$1,990 total
includes taxes & fees
9 Aug - 10 Aug
Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
Terrace/patio

17. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (35 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is HK$1,059
HK$1,737 total
includes taxes & fees
11 Aug - 12 Aug
Mountain View Bungalow in Front Royal
Property grounds

18. Apple Mountain Retreat

Apple Mountain Retreat
Linden
9.8 out of 10, Exceptional, (27 reviews)
"Great place to stayed "
United States
Mike F.
The price is HK$1,059
HK$1,825 total
includes taxes & fees
12 Aug - 13 Aug
Apple Mountain Retreat
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$2,906 total
includes taxes & fees
9 Aug - 10 Aug
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Property grounds

20. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (48 reviews)
"What an absolutely lovely and peaceful place to stay! We had a wonderful visit. "
United States
Stephanie T.
The price is HK$1,129
HK$2,405 total
includes taxes & fees
10 Aug - 11 Aug
Newly renovated Farm cottage with Mountain views
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

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

8/10 Good
"Had to go back to desk 2 times after checking in while my wife stood outside our room with luggage in the hall because the keys didn't work. Very frustrating! Also, only 7 channels worked on the TV, was told this was Comcast fault."
Jason 1-night trip
Posted 6 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG

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?

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub: This holiday home rental outside of Winchester is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Winchester?

Choose from 13 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Nalls Farm Market are a couple of the family-friendly sights, whereas cultural attractions include Winchester Little Theater and Museum of the Shenandoah Valley. Other places in town to visit include Stonewall Jackson's Headquarters and Patsy Cline Historic House.

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.