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 Shepherdstown
4.95 out of 5 average rating, 260 reviews1 Bedroom Apt in Historic Downtown Shepherdstown
Apartment in Bluemont
4.96 out of 5 average rating, 141 reviewsCharming private apartment
Apartment in Shepherdstown
4.91 out of 5 average rating, 144 reviewsDowntown Modern Studio apartment | History & Dining steps away
Apartment in Staunton
4.95 out of 5 average rating, 280 reviewsTravelers Nook - close to downtown
Apartment in Elkton
4.98 out of 5 average rating, 193 reviewsAwesome View
Apartment in Fredericksburg
4.92 out of 5 average rating, 226 reviewsAdorable 1-Bedroom Loft in Downtown Fredericksburg
Apartment in Davis
4.94 out of 5 average rating, 322 reviewsDoc's Guesthouse - Hospital for the Soul!
Apartment in Gettysburg
4.97 out of 5 average rating, 427 reviewsHome Away From Home - Apt in Historic Gettysburg
Private apartment rentals
Apartment in Bethesda
4.99 out of 5 average rating, 253 reviewsImmaculate Apartment in Downtown Bethesda
Apartment in Sykesville
4.98 out of 5 average rating, 284 reviewsIn the Heart of Sykesville! 2 Bedroom Suite
Apartment in Frederick
4.9 out of 5 average rating, 142 reviewsYour own "Tiny House"
Apartment in Cumberland
4.99 out of 5 average rating, 153 reviewsAllegheny Suite in Corner Tavern Residences
Apartment in Washington
4.98 out of 5 average rating, 460 reviewsCapHill Oasis-Scenic Park View-FreeParking!
Apartment in Gettysburg
4.99 out of 5 average rating, 340 reviewsQuiet Country Setting
Apartment in Bedford
4.96 out of 5 average rating, 269 reviewsSpacious & Private 2-Bedroom Apartment
Apartment in Harrisonburg
4.92 out of 5 average rating, 668 reviewsRestful Hilltop Apartment: No cleaning fees!
Apartment rentals with a hot tub
Apartment in Madison
4.9 out of 5 average rating, 230 reviewsThe Studio at Dark Run Retreat
Apartment in McGaheysville
4.95 out of 5 average rating, 186 reviewsHenrys Mountain Haven at Massanutten Resort
Apartment in Oakland
4.9 out of 5 average rating, 113 reviewsPrivate Unit on Farm with Kitchen & Balcony
Apartment in Stanardsville
4.68 out of 5 average rating, 334 reviewsWhite Lotus Suite
Apartment in Berkeley Springs
4.77 out of 5 average rating, 47 reviewsThe Parlor Suite
Apartment in Lovettsville
5.0 out of 5 average rating, 28 reviewsEnjoy peace, quite and the beauty!
Apartment in Grantsville
4.97 out of 5 average rating, 91 reviewsYoder School Guest House with wifi and hot tub
Apartment in La Vale
4.89 out of 5 average rating, 28 reviewsSweet 68
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
$30 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 Deep Creek Lake
- Apartment rentals Baltimore
- Apartment rentals Virginia
- Serviced apartment rentals Virginia
- Rentals with a washer and dryer Winchester
- Cottage rentals Winchester
- House rentals Winchester
- Monthly Rentals Winchester
- Family-friendly rentals Winchester
- Rentals with a patio Winchester
- Pet-friendly rentals Winchester
- Rentals with outdoor seating Winchester
- Cabin rentals Winchester
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes