Vacation rentals in Winchester
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
Cabin in Augusta ( Capon Bridge)
4.96 out of 5 average rating, 131 reviewsNirvana, Mountain View
Cabin in Lost River
4.95 out of 5 average rating, 111 reviewsRustic and stylish mountain getaway
Farm stay in Round Hill
4.94 out of 5 average rating, 346 reviewsCome and get your goat on!
Cabin in Lost City
4.97 out of 5 average rating, 248 reviewsHigh View Hideaway - A Cozy Lost River Cabin
Loft in Purcellville
4.99 out of 5 average rating, 286 reviews"When Pigs Fly" Airbnb Most Hospitable Host in VA
Farm stay in Romney
4.98 out of 5 average rating, 285 reviewsPotomac Hills B&B on 15 Acre Farm with a View
Guest suite in Summit Point
4.97 out of 5 average rating, 128 reviewsThe Big Room - Historic Schoolhouse
Home in Strasburg
4.89 out of 5 average rating, 228 reviewsShenandoah Siesta
Other great vacation rentals in Winchester
Apartment in Winchester
4.97 out of 5 average rating, 77 reviewsHistoric Wisteria House on Old Town Walking Mall
Cottage in Winchester
4.9 out of 5 average rating, 98 reviewsLockley Cottage at Historic Perry Farm
Townhouse in Winchester
4.93 out of 5 average rating, 40 reviewsBrewhouse renovated row house steps from downtown
Place to stay in Winchester
4.86 out of 5 average rating, 43 reviewsCrash Landing
Condo in Winchester
4.98 out of 5 average rating, 49 reviewsHistoric District Downtown Winchester
Guest suite in Winchester
4.92 out of 5 average rating, 51 reviewsRetro Vibe Studio
Home in Winchester
4.9 out of 5 average rating, 10 reviewsCabin in Historic Old Town Winchester
Apartment in Winchester
5.0 out of 5 average rating, 5 reviewsCameron Loft 2 Story Studio with 1.5 Bath Downtown
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 apartment rentals with a dedicated workspace in Winchester?
Yes! Work meets play with ease at over 20 apartment rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.
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 house rentals in Winchester have wifi?
Absolutely! We offer over 30 house rentals with wifi in Winchester. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Winchester have self check-in?
Absolutely! We offer over 20 apartment rentals with self check-in in Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly apartment rentals in Winchester?
Four-legged friends are welcome in Winchester. Choose from more than 10 apartment rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Winchester?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with self check-in, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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
- New York Vacation rentals
- Jersey City Vacation rentals
- Rentals with a washer and dryer Winchester
- Rentals with outdoor seating Winchester
- Cottage rentals Winchester
- Monthly Rentals Winchester
- Cabin rentals Winchester
- Apartment rentals Winchester
- House rentals Winchester
- Family-friendly rentals Winchester
- Rentals with a patio Winchester
- Pet-friendly 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