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

Winchester Vacation 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 vacation 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 traveler
The price is AED 367
AED 645 total
includes taxes & fees
19 Aug - 20 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 AED 444
AED 1,113 total
includes taxes & fees
19 Aug - 20 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.
The price is AED 404
AED 707 total
includes taxes & fees
25 Aug - 26 Aug
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 AED 507
AED 845 total
includes taxes & fees
31 Aug - 1 Sep
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 AED 544
AED 965 total
includes taxes & fees
13 Aug - 14 Aug
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 AED 477
AED 791 total
includes taxes & fees
30 Aug - 31 Aug
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 AED 579
AED 1,149 total
includes taxes & fees
9 Aug - 10 Aug
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 AED 404
AED 728 total
includes taxes & fees
19 Aug - 20 Aug
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 AED 533
AED 675 total
includes taxes & fees
10 Aug - 11 Aug
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 AED 716
AED 911 total
includes taxes & fees
3 Sep - 4 Sep
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 AED 727
AED 1,298 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 AED 680
AED 1,169 total
includes taxes & fees
19 Aug - 20 Aug
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 AED 536
AED 957 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 traveler
The price is AED 275
AED 786 total
includes taxes & fees
16 Aug - 17 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 AED 772
AED 932 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 AED 496
AED 814 total
includes taxes & fees
16 Aug - 17 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 AED 496
AED 859 total
includes taxes & fees
8 Aug - 9 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 AED 753
AED 1,361 total
includes taxes & fees
19 Aug - 20 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 AED 529
AED 1,126 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 5 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG

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?

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub: This vacation home near Winchester is located on a river and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Winchester?

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

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Nalls Farm Market are a couple of 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 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.