Apartment holiday rentals in Winchester
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Top-rated apartment rentals in Winchester
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester apartment rentals
Weekly apartment rentals
Flat in Shepherdstown
4.95 out of 5 average rating, 256 reviews1 Bedroom Apt in Historic Downtown Shepherdstown
8–15 Jan
Flat in Bethesda
4.99 out of 5 average rating, 246 reviewsImmaculate Apartment in Downtown Bethesda
30 Dec – 6 Jan
Flat in Harpers Ferry
4.99 out of 5 average rating, 363 reviewsTaylor Den
27 Jul – 3 Aug
Flat in Sykesville
4.82 out of 5 average rating, 343 reviewsQuiet Studio Basement Apartment
8–15 Oct
Flat in Bluemont
4.96 out of 5 average rating, 140 reviewsCharming private apartment
2–9 Dec
Flat in Harrisonburg
4.96 out of 5 average rating, 430 reviewsA Place to Rest
18–25 Sept
Flat in Bentonville
4.98 out of 5 average rating, 239 reviewsFull Circle Farm Shenandoah Valley No Cleaning Fee
19–26 Sept
Flat in Harrisonburg
4.92 out of 5 average rating, 660 reviewsRestful Hilltop Apartment: No cleaning fees!
3–10 Sept
Private apartment rentals
Flat in Cumberland
4.99 out of 5 average rating, 147 reviewsAllegheny Suite in Corner Tavern Residences
17–24 Oct
Flat in Madison
4.9 out of 5 average rating, 229 reviewsThe Studio at Dark Run Retreat
9–16 Jun
Flat in Shepherdstown
4.91 out of 5 average rating, 140 reviewsDowntown Modern Studio apartment | History & Dining steps away
20–27 Aug
Flat in Frederick
4.9 out of 5 average rating, 139 reviewsYour own "Tiny House"
28 Jun – 5 Jul
Flat in Occoquan
4.89 out of 5 average rating, 419 reviewsAnne’s River View, couples, Historic Occoquan,hike
15–22 Aug
Flat in Rockwood
4.9 out of 5 average rating, 436 reviewsTaking reservations *Newly Renovated* GORGEOUS!
3–10 Jan
Flat in Somerset
4.98 out of 5 average rating, 179 reviewsCreekside
7–14 Sept
Flat in Silver Spring
4.93 out of 5 average rating, 395 reviewsEscape to a Sunny Apartment in a Quiet D.C. Suburb
11–18 Sept
Apartment rentals with a hot tub
Flat in McGaheysville
4.95 out of 5 average rating, 186 reviewsHenrys Mountain Haven at Massanutten Resort
3–10 Dec
Flat in Oakland
4.9 out of 5 average rating, 113 reviewsPrivate Unit on Farm with Kitchen & Balcony
28 Aug – 4 Sept
Flat in Stanardsville
4.68 out of 5 average rating, 332 reviewsWhite Lotus Suite
22–29 Jan
Flat in Berkeley Springs
4.77 out of 5 average rating, 44 reviewsThe Parlor Suite
23–30 Sept
Flat in Grantsville
4.97 out of 5 average rating, 90 reviewsYoder School Guest House with wifi and hot tub
3–10 Jan
Flat in Lovettsville
5.0 out of 5 average rating, 28 reviewsEnjoy peace, quite and the beauty!
9–16 Mar
Flat in Nokesville
4.89 out of 5 average rating, 9 reviewsCouples countryside escape
19–26 Sept
Flat in La Vale
4.93 out of 5 average rating, 27 reviewsSweet 68
1–8 Sept
Quick stats about flat rentals in Winchester
Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
2.8K reviews
Nightly prices starting at
£24 before taxes and fees
Destinations to explore
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