Winchester vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Winchester
Guests agree: these vacation rentals 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 vacation rentals
Other great vacation rentals in Winchester
Guest suite in Winchester
4.79 out of 5 average rating, 280 reviewsSafe, cozy oasis with private living & bath.
Cottage in Shepherdstown
4.96 out of 5 average rating, 186 reviewsThe GW Hollida Cottage of Shepherdstown
Tiny home in Linville
4.99 out of 5 average rating, 604 reviewsThe spring house at Thistle Hollow
Cabin in Lost City
4.97 out of 5 average rating, 252 reviewsHigh View Hideaway - A Cozy Lost River Cabin
Cabin in Lost River
4.96 out of 5 average rating, 112 reviewsRustic and stylish mountain getaway
Cabin in Augusta ( Capon Bridge)
4.96 out of 5 average rating, 131 reviewsNirvana, Mountain View
Home in Inwood
4.89 out of 5 average rating, 553 reviewsArden House, Inwood WV
Guesthouse in Round Hill
4.98 out of 5 average rating, 376 reviewsPrivate Carriage House
Other great vacation rentals in Winchester
Apartment in Winchester
4.94 out of 5 average rating, 51 reviewsNewly repurposed Historic Home in Winchester VA!
Apartment in Winchester
4.97 out of 5 average rating, 77 reviewsHistoric Wisteria House on Old Town Walking Mall
Place to stay in Winchester
4.88 out of 5 average rating, 50 reviewsCrash Landing
Apartment in Winchester
5.0 out of 5 average rating, 11 reviewsCameron Corner: King Bed & Office Downtown
Home in Winchester
4.92 out of 5 average rating, 26 reviewsMisty Meadow has quite setting in the country.
Home in Winchester
4.92 out of 5 average rating, 12 reviewsCabin in Historic Old Town Winchester
Townhouse in Winchester
4.93 out of 5 average rating, 41 reviewsBrewhouse renovated row house steps from downtown
Condo in Winchester
4.98 out of 5 average rating, 50 reviewsHistoric District Downtown Winchester
Quick stats about vacation rentals in Winchester
Total rentals
90 properties
Wifi availability
90 properties include access to wifi
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
6K reviews
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Winchester?
Yes! Work meets play with ease at over 50 vacation rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winchester?
Four-legged friends are welcome in Winchester. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Winchester?
Experience the best of Winchester with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Winchester have wifi?
Absolutely! We offer over 30 apartment rentals with wifi in Winchester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winchester have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winchester?
Winchester has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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
- Rentals with a patio Winchester
- Pet-friendly rentals Winchester
- Rentals with a washer and dryer Winchester
- Family-friendly rentals Winchester
- Cottage rentals Winchester
- Cabin rentals Winchester
- House rentals Winchester
- Rentals with outdoor seating Winchester
- Monthly Rentals Winchester
- Apartment 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