Best Vacation Homes in Winchester
House
10.0(109 Reviews)
2 Bedrooms
2 Baths
6 Guests
1800 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Pet Friendly
CA $789/Night
7 Nights - CA $5,525
House
10.0(2 Reviews)
4 Bedrooms
4 Baths
6 Guests
4380.91 ft²
- Fireplace/Heating
- Pet Friendly
Parking
Internet
CA $533/Night
7 Nights - CA $3,734
Hotel
9.6(565 Reviews)
1 Bath
Pool- Balcony/Terrace
Breakfast
Kitchen
CA $175/Night
7 Nights - CA $1,224
Cabin
10.0(45 Reviews)
1 Bedroom
1 Bath
2 Guests
1250 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $304/Night
7 Nights - CA $2,131
House
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
2497.23 ft²
Oceanfront- Fireplace/Heating
Ocean View
View
CA $548/Night
7 Nights - CA $3,840
Ski Chalet
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
912 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $1,041/Night
7 Nights - CA $7,289
Cabin
9.2(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $209/Night
7 Nights - CA $1,462
House
8.0(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Internet
CA $240/Night
7 Nights - CA $1,684
Winchester Luxury Rentals
Ski Chalet
10.0(80 Reviews)
4 Bedrooms
3 Baths
10 Guests
2800 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $9,711/Night
7 Nights - CA $67,980
House
10.0(33 Reviews)
7 Bedrooms
8 Baths
16 Guests
10000 ft²
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
CA $2,783/Night
7 Nights - CA $19,480
Villa
6 Bedrooms
7 Baths
13 Guests
9999.67 ft²
- Fireplace/Heating
- Pool
- View
- Parking
CA $2,614/Night
7 Nights - CA $18,301
Villa
10.0(2 Reviews)
6 Bedrooms
6 Baths
13 Guests
10000 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $2,568/Night
7 Nights - CA $17,977
Cabin
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
CA $2,265/Night
7 Nights - CA $15,854
House
10.0(80 Reviews)
5 Bedrooms
6 Baths
14 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $2,030/Night
7 Nights - CA $14,212
House
9.8(265 Reviews)
6 Bedrooms
4 Baths
14 Guests
- Private Pool
- Hot Tub
Spa- Fireplace/Heating
CA $1,988/Night
7 Nights - CA $13,913
Hotel
7.8(7 Reviews)
6 Baths
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
CA $1,651/Night
7 Nights - CA $11,557
Winchester Pet Friendly Vacation Rentals
Apartment
7.2(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
CA $289/Night
7 Nights - CA $2,026
Villa
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
1323.96 ft²
- Hot Tub
- Balcony/Terrace
- View
- Pet Friendly
CA $1,251/Night
7 Nights - CA $8,755
Hotel
9.2(2276 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Pet Friendly
CA $173/Night
7 Nights - CA $1,209
Apartment
7.0(8 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pet Friendly
- Air Conditioner
- Internet
- Child Friendly
CA $272/Night
7 Nights - CA $1,905
House
9.8(12 Reviews)
3 Bedrooms
2 Baths
5 Guests
2002.09 ft²
- Balcony/Terrace
- View
- Pet Friendly
- Parking
CA $472/Night
7 Nights - CA $3,306
New
Cabin
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $250/Night
7 Nights - CA $1,752
New
House
2 Bedrooms
2 Baths
10 Guests
1100 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $348/Night
7 Nights - CA $2,439
House
10.0(86 Reviews)
4 Bedrooms
4 Baths
9 Guests
3800 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
CA $1,120/Night
7 Nights - CA $7,838
Winchester Large Vacation Homes
House
8.6(43 Reviews)
3 Bedrooms
2 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $781/Night
7 Nights - CA $5,464
House
9.7(7 Reviews)
6 Bedrooms
4 Baths
14 Guests
3304.52 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $524/Night
7 Nights - CA $3,666
House
10.0(10 Reviews)
5 Bedrooms
3 Baths
10 Guests
2761 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $373/Night
7 Nights - CA $2,613
House
9.7(3 Reviews)
2 Bedrooms
2 Baths
10 Guests
2002.09 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Child Friendly
CA $266/Night
7 Nights - CA $1,863
House
5 Bedrooms
2 Baths
13 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $383/Night
7 Nights - CA $2,679
Ski Chalet
10.0(52 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
CA $853/Night
7 Nights - CA $5,971
House
10.0(42 Reviews)
4 Bedrooms
3 Baths
14 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $553/Night
7 Nights - CA $3,872
House
10.0(29 Reviews)
5 Bedrooms
4 Baths
8 Guests
7707 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $700/Night
7 Nights - CA $4,898
Why Choose Rent By Owner for your Winchester Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Winchester
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this destination ensures you can enjoy the area's attractions and experience its unique seasonal charm, making your stay in Winchester, Virginia, an unforgettable adventure.
Peak Season Highlights
Spring (March to May)
During this time, the region experiences mild temperatures and blooming landscapes, making it perfect for exploring the local scenery and outdoor attractions.
Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
Fall (September to November)
The area is vibrant with colorful foliage, creating an ideal setting for outdoor activities and enjoying the scenic views of this historic destination.
Average Temperature Daytime: 65-70°F - Nighttime: 45-50°F
Off-Season Highlights
Summer (June to August)
While summer brings warmer weather, this is a quieter period for visitors, offering more tranquility and lower rates for your vacation rentals here.
Average Temperature Daytime: 80-85°F - Nighttime: 60-65°F
Winter (December to February)
With cooler temperatures and fewer travelers, winter allows you to enjoy a peaceful retreat, often at more affordable rates in the region.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Weekly Weather Forecast for Winchester
How to Book Your Winchester Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Winchester
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining spaces perfect for meals al fresco amidst the scenic surroundings of Winchester, Virginia.
- Take advantage of private patios or decks that offer a relaxing spot to unwind after exploring the area.
- Utilize landscaped gardens or yard areas ideal for leisurely strolls or outdoor activities.
- Make use of outdoor grills for hosting barbecues in the charming setting of the region.
- Relax by a fire pit during cool evenings, creating a cozy atmosphere under the stars.
- Benefit from access to spacious lawns suitable for family games and picnics in this part of Virginia.
- Discover inviting porches or verandas that provide a peaceful place to enjoy the fresh air and views.
Top Attractions Around Winchester
What attractions are nearby?
In this charming destination, you can explore a variety of outdoor activities, historical sites, and local attractions that offer a perfect blend of relaxation and adventure for your stay.
Family Activities
- Wyndham Championship Golf Course: Enjoy a family-friendly day on the greens at this popular golf course in the region, offering scenic views and beginner-friendly options.
- Old Town Winchester Historic District: Take a stroll through the charming streets filled with historic sites, shops, and eateries that highlight the area's rich heritage.
- Shenandoah Valley Discovery Museum: Engage your children with interactive exhibits and hands-on activities designed to inspire curiosity and learning in a fun environment nearby.
- Jim Barnett Park: Relax outdoors with playgrounds, walking trails, and open spaces perfect for picnics or simply enjoying the fresh air with your family in the area.
Adult Activities
- Historic Downtown Winchester Tours: Explore the charming streets filled with boutique shops, galleries, and restaurants that showcase the area's rich history and vibrant local culture.
- Winchester Cider Farm Visit: Discover the region’s apple heritage by sampling locally crafted ciders at one of the area’s renowned cider farms, perfect for a relaxing afternoon.
- Valley Art & Frame Gallery Experience: Enjoy browsing the extensive collection of contemporary and traditional artwork in this popular gallery nestled within the region's artistic community.
- Harper’s Ferry Day Trip: Take a scenic drive to nearby Harper’s Ferry for outdoor adventures, historic sites, and stunning river views that highlight this picturesque part of Virginia’s surroundings.
Other Places to Stay in Winchester, VA
Warren County
Front Royal
Frederick County
Happy Creek
Old Town Winchester
Strasburg
Clarke County
Berryville
Bluemont
Russell
Stephens City
Winchester Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Heritage Sites: Take time to visit the area's historical landmarks to gain a deeper understanding of its rich past and make your stay more meaningful.
- Discover Scenic Outdoors: Use your vacation to enjoy the region’s parks and natural beauty, perfect for outdoor activities and relaxing in nature.
- Savor Regional Cuisine: Indulge in the local flavors by dining at nearby eateries or preparing meals with fresh, regional ingredients in your vacation rental.
- Plan Convenient Excursions: Organize day trips to nearby attractions to maximize your experience without sacrificing comfort during your stay here.
Transportation Options
- Winchester Transit System: This local bus service offers convenient and affordable transportation options throughout the area, making it easy to explore nearby attractions from your vacation rental.
- Amtrak Station in Winchester: Connecting you to major cities along the East Coast, the Amtrak station provides a comfortable and reliable way to arrive at this destination by train.
- Rental Cars: Car rental services here give you the flexibility to discover the region at your own pace, whether you're heading to historical sites or scenic spots around this destination.
- Taxis and Rideshares: Available throughout the area, taxis and rideshare services like Uber and Lyft offer quick and convenient transportation options for short trips within this destination.
Local Customs Options
- Historical Reenactments: You can witness authentic Civil War reenactments here, reflecting the area's rich historical heritage.
- Local Craftsmanship: Supporting local artisans by exploring crafts and handmade goods is a cherished custom in this region.
- Southern Hospitality: Expect warm welcomes and courteous interactions that embody the friendly spirit of the area’s community.
- Traditional Festivals: Participating in seasonal festivals and events offers a glimpse into the longstanding cultural traditions of here.
Frequently Asked Questions About Winchester?
1. What are the top vacation rentals in Winchester?
There are a lot of options in Winchester. If you plan on staying in the Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winchester:
- Dog Friendly Skyline Drive Retreat: 3 King Suites, Views & Firepit! 1pm checkout
- Spectacular Cottage with Shenandoah River Views
- Fantasy Cottage: Private Pond, Waterfall, Hot Tub
- Rolling River Farm: Exquisite Riverfront Paradise
- Spacious Cabin on Cedar Creek, Shenandoah's hidden getaway!
- Riverfront - Happy Peach on the Shenandoah
- Country Elegance overlooking the Shenandoah River
- The Nest at Chester Gap
- Whiskey Hill Cabin a mountain escape in Virginia wine country
- Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains
2. How many vacation rentals have private pools in Winchester?
There are 20 vacation rentals with private pools near Winchester. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Winchester are best for families?
If you are looking for a family-friendly vacation home in Winchester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winchester:
4. How many Rentbyowner vacation rentals are available in Winchester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 436 in the Winchester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winchester.
5. What is the cancellation policy for vacation rentals in Winchester, Virginia?
Cancellation policies vary depending on the individual listing. To understand the specific terms, review the cancellation policy provided in the listing details or contact the property owner directly.
6. How do I ensure my booking in Winchester, Virginia, is secure and protected?
Booking through verified listings with secure payment options helps safeguard your reservation. Always verify the host's credentials and read reviews to ensure a trustworthy experience for your stay here.
7. Are there any additional fees I should be aware of when booking a rental in this destination?
Additional fees such as cleaning, service charges, or local taxes may apply. These details are usually listed during the booking process or can be clarified by reaching out to the property owner beforehand.
8. What amenities are typically included in vacation rentals in this area?
Most rentals in this region offer essential amenities like Wi-Fi, kitchen facilities, and parking. For specific features, review the listing description or contact the host directly to confirm what’s available during your stay.
9. How close are the vacation rentals in Winchester to local attractions and transportation?
Many properties are conveniently located near key points of interest and transportation options. To find the best fit for your plans, check the location details in each listing or ask the host for guidance.
Winchester Top Rated Vacation Rentals
Cabin
10.0(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
2200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $827/Night
7 Nights - CA $5,787
Hotel
9.4(1007 Reviews)
1 Bath
- Spa
- Pool
- Breakfast
- Kitchen
CA $202/Night
7 Nights - CA $1,415
Hotel
9.2(1441 Reviews)
1 Bath
- Pool
- Breakfast
- Parking
- Air Conditioner
CA $126/Night
7 Nights - CA $884
CA $137/Night
7 Nights - CA $957
Hotel
9.2(886 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
CA $167/Night
7 Nights - CA $1,166
Hotel
9.2(851 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
CA $138/Night
7 Nights - CA $966
Hotel
9.1(648 Reviews)
10 Baths
425.18 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
CA $377/Night
7 Nights - CA $2,642
Hotel
9.1(359 Reviews)
1 Bath
290.63 ft²
- Oceanfront
Skiing- Fireplace/Heating
- Pool
CA $148/Night
7 Nights - CA $1,039
