Apartment vacation rentals in Winchester
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Winchester
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester apartment rentals
Weekly apartment rentals
Apartment in Fredericksburg
4.92 out of 5 average rating, 222 reviewsAdorable 1-Bedroom Loft in Downtown Fredericksburg
Jul 16 – 23
Apartment in Elkton
4.98 out of 5 average rating, 190 reviewsAwesome View
Feb 2 – 9
Apartment in Bethesda
4.99 out of 5 average rating, 245 reviewsImmaculate Apartment in Downtown Bethesda
Dec 7 – 14
Apartment in Bentonville
4.98 out of 5 average rating, 239 reviewsFull Circle Farm Shenandoah Valley No Cleaning Fee
Jan 6 – 13
Apartment in Shepherdstown
4.95 out of 5 average rating, 256 reviews1 Bedroom Apt in Historic Downtown Shepherdstown
Apr 12 – 19
Apartment in Harrisonburg
4.92 out of 5 average rating, 660 reviewsRestful Hilltop Apartment: No cleaning fees!
Oct 19 – 26
Apartment in Bluemont
4.96 out of 5 average rating, 140 reviewsCharming private apartment
Jun 25 – Jul 2
Apartment in Shepherdstown
4.91 out of 5 average rating, 140 reviewsDowntown Modern Studio apartment | History & Dining steps away
Jun 24 – Jul 1
Private apartment rentals
Apartment in Occoquan
4.89 out of 5 average rating, 419 reviewsAnne’s River View, couples, Historic Occoquan,hike
Oct 20 – 27
Apartment in Gettysburg
4.97 out of 5 average rating, 425 reviewsHome Away From Home - Apt in Historic Gettysburg
Jan 5 – 12
Apartment in Bedford
4.95 out of 5 average rating, 266 reviewsSpacious & Private 2-Bedroom Apartment
Jun 21 – 28
Apartment in Gettysburg
4.96 out of 5 average rating, 224 reviewsTop O' The Stairs
Apr 8 – 15
Apartment in Madison
4.9 out of 5 average rating, 229 reviewsThe Studio at Dark Run Retreat
Jul 11 – 18
Apartment in Frederick
4.87 out of 5 average rating, 207 reviewsDowntown Frederick Modern Studio
Aug 6 – 13
Apartment in Frederick
4.95 out of 5 average rating, 104 reviewsKing Bed Apt./Carroll Creek Promenade w/views!!
Nov 27 – Dec 4
Apartment in Frederick
4.9 out of 5 average rating, 138 reviewsYour own "Tiny House"
Aug 29 – Sep 5
Apartment rentals with a hot tub
Apartment in McGaheysville
4.95 out of 5 average rating, 185 reviewsHenrys Mountain Haven at Massanutten Resort
Dec 1 – 8
Apartment in Oakland
4.9 out of 5 average rating, 113 reviewsPrivate Unit on Farm with Kitchen & Balcony
Aug 25 – Sep 1
Apartment in Stanardsville
4.68 out of 5 average rating, 331 reviewsWhite Lotus Suite
Oct 26 – Nov 2
Apartment in Grantsville
4.97 out of 5 average rating, 90 reviewsYoder School Guest House with wifi and hot tub
Dec 31 – Jan 7
Apartment in Berkeley Springs
4.77 out of 5 average rating, 44 reviewsThe Parlor Suite
Aug 26 – Sep 2
Apartment in La Vale
4.92 out of 5 average rating, 26 reviewsSweet 68
Jul 12 – 19
Apartment in Lovettsville
5.0 out of 5 average rating, 28 reviewsEnjoy peace, quite and the beauty!
Jan 23 – 30
Apartment in Nokesville
4.89 out of 5 average rating, 9 reviewsCouples countryside escape
Jan 9 – 16
Quick stats about apartment 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
R555 ZAR before taxes and fees
Destinations to explore
- Baltimore Vacation rentals
- Cabins Vacation rentals
- Arlington Vacation rentals
- Charlottesville Vacation rentals
- Alexandria Vacation rentals
- Bethesda Vacation rentals
- Annapolis Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- Apartment rentals United States
- Serviced apartment rentals United States
- Serviced apartment rentals Washington
- Apartment rentals Washington
- Apartment rentals Baltimore
- Serviced apartment rentals Virginia
- Apartment rentals Virginia
- Family-friendly rentals Winchester
- House rentals Winchester
- Cottage rentals Winchester
- Rentals with a patio Winchester
- Pet-friendly rentals Winchester
- Rentals with outdoor seating Winchester
- Cabin rentals Winchester
- Monthly Rentals Winchester
- Rentals with a washer and dryer Winchester
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom