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 Elkton
4.98 out of 5 average rating, 190 reviewsAwesome View
7–14 Feb
Flat in Shepherdstown
4.95 out of 5 average rating, 256 reviews1 Bedroom Apt in Historic Downtown Shepherdstown
4–11 Oct
Flat in Harpers Ferry
4.99 out of 5 average rating, 363 reviewsTaylor Den
11–18 Jun
Flat in Occoquan
4.89 out of 5 average rating, 417 reviewsAnne’s River View, couples, Historic Occoquan,hike
16–23 Oct
Flat in Bentonville
4.98 out of 5 average rating, 239 reviewsFull Circle Farm Shenandoah Valley No Cleaning Fee
15–22 Mar
Flat in Sykesville
4.98 out of 5 average rating, 280 reviewsIn the Heart of Sykesville! 2 Bedroom Suite
8–15 Jan
Flat in Sykesville
4.82 out of 5 average rating, 342 reviewsQuiet Studio Basement Apartment
19–26 Dec
Flat in Harrisonburg
4.97 out of 5 average rating, 335 reviewsPrivate suite close to JMU quiet neighborhood
9–16 Jan
Private apartment rentals
Flat in Bluemont
4.96 out of 5 average rating, 140 reviewsCharming private apartment
15–22 Nov
Flat in Washington
4.98 out of 5 average rating, 315 reviewsGeorgetown Modern Chic 1 Bedroom
28 Dec – 4 Jan
Flat in Shepherdstown
4.91 out of 5 average rating, 140 reviewsDowntown Modern Studio apartment | History & Dining steps away
4–11 Jul
Flat in Frederick
4.87 out of 5 average rating, 205 reviewsDowntown Frederick Modern Studio
11–18 Jan
Flat in Gettysburg
4.96 out of 5 average rating, 224 reviewsTop O' The Stairs
31 Mar – 7 Apr
Flat in Harrisonburg
4.97 out of 5 average rating, 261 reviewsSpacious Modern Studio, Walk to Downtown + JMU
29 Jul – 5 Aug
Flat in Madison
4.9 out of 5 average rating, 229 reviewsThe Studio at Dark Run Retreat
7–14 Aug
Flat in Dickerson
4.82 out of 5 average rating, 121 reviewsStudio apartment at Sugarloaf Log House
29 Oct – 5 Nov
Apartment rentals with a hot tub
Flat in McGaheysville
4.95 out of 5 average rating, 185 reviewsHenrys Mountain Haven at Massanutten Resort
4–11 Dec
Flat in Oakland
4.9 out of 5 average rating, 113 reviewsPrivate Unit on Farm with Kitchen & Balcony
11–18 Apr
Flat in Stanardsville
4.68 out of 5 average rating, 330 reviewsWhite Lotus Suite
20–27 Nov
Flat in Berkeley Springs
4.77 out of 5 average rating, 43 reviewsThe Parlor Suite
5–12 Sep
Flat in La Vale
4.92 out of 5 average rating, 26 reviewsSweet 68
29 Oct – 5 Nov
Flat in Grantsville
4.97 out of 5 average rating, 90 reviewsYoder School Guest House with wifi and hot tub
4–11 May
Flat in Lovettsville
5.0 out of 5 average rating, 28 reviewsEnjoy peace, quite and the beauty!
29 Dec – 5 Jan
Flat in Arlington
4.75 out of 5 average rating, 12 reviewsSpacious Apartment Near Metro w/ Hot Tub
22–29 Jun
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
€ 28 before taxes and fees
Destinations to explore
- Baltimore Holiday rentals
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