Best Winchester Vacation Rentals
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Guest favorite
Villa Maud
- In-room breakfast
- Free parking
- 24-hour reception
- Air conditioning
- Golf centre
- Sun terrace
Located 2.8 km from Snicker's Gap Turnpike, the 3-room Villa Maud Middleburg boasts a swimming pool with a hot tub.
A sun deck, a picnic area, and a golf course, as well as karaoke are among entertainment options for guests. Such activities as hiking and horseback riding can be organised on site.
Villa Maud
- In-room breakfast
- Free parking
- 24-hour reception
- Air conditioning
- Golf centre
- Sun terrace
Villa Maud
Located 2.8 km from Snicker's Gap Turnpike, the 3-room Villa Maud Middleburg boasts a swimming pool with a hot tub.
A sun deck, a picnic area, and a golf course, as well as karaoke are among entertainment options for guests. Such activities as hiking and horseback riding can be organised on site.
Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Jacuzzi
- Sun terrace
During the stay at the 2-bedroom Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds Front Royal villa, guests can indulge in a Jacuzzi or visit Warren Rifles Confederate Msm Museum, located 3.9 km away. Located within a 10-minute drive of Shenandoah Valley Overlook, the villa provides Wi-Fi and a private parking lot.
Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Jacuzzi
- Sun terrace
Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds
During the stay at the 2-bedroom Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds Front Royal villa, guests can indulge in a Jacuzzi or visit Warren Rifles Confederate Msm Museum, located 3.9 km away. Located within a 10-minute drive of Shenandoah Valley Overlook, the villa provides Wi-Fi and a private parking lot.
Cozy - Experience It All
- Cookware/ Kitchen utensils
- On-site car park
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Outdoor swimming pool
Featuring an outdoor swimming pool, the 2-bedroom Cozy - Experience It All Berkeley Springs villa is suitable for up to 4 people and is located within a 6-km distance of the english-style Samuel Taylor Suit Cottage Castle. Providing guests with Wi-Fi and a car park, the property is approximately a 10-minute drive from Berkeley Springs Brewing Co.
Cozy - Experience It All
- Cookware/ Kitchen utensils
- On-site car park
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Outdoor swimming pool
Cozy - Experience It All
Featuring an outdoor swimming pool, the 2-bedroom Cozy - Experience It All Berkeley Springs villa is suitable for up to 4 people and is located within a 6-km distance of the english-style Samuel Taylor Suit Cottage Castle. Providing guests with Wi-Fi and a car park, the property is approximately a 10-minute drive from Berkeley Springs Brewing Co.
High Meadows Estate
- Free parking
- Air conditioning
- Flat-screen TV
- Heating
- Terrace
- Garden area
Situated 2.7 km from Great Country Farms, High Meadows Estate Villa Purcellville invites guests to relax at a terrace.
Guests can enjoy activities like diving, hiking, and horseback riding.
High Meadows Estate
- Free parking
- Air conditioning
- Flat-screen TV
- Heating
- Terrace
- Garden area
High Meadows Estate
Situated 2.7 km from Great Country Farms, High Meadows Estate Villa Purcellville invites guests to relax at a terrace.
Guests can enjoy activities like diving, hiking, and horseback riding.
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Top location
Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Jacuzzi
- Terrace
Located 18 minutes' walk from Deer Lake, the 3-bedroom Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger Villa Front Royal entices guests to relax in a Jacuzzi. This 2-bathroom villa can host up to 8 guests, offering the opportunity to enjoy a terrace.
Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Jacuzzi
- Terrace
Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger
Located 18 minutes' walk from Deer Lake, the 3-bedroom Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger Villa Front Royal entices guests to relax in a Jacuzzi. This 2-bathroom villa can host up to 8 guests, offering the opportunity to enjoy a terrace.
The Dulles Executive Resort Near Dulles Airport With Private Office
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Terrace
Nestled about a 10-minute ride from ArtInsights Gallery of Film and Contemporary Art, the 1-bedroom The Dulles Executive Resort Near Dulles Airport With Private Office Herndon villa is boasting a terrace, a shared lounge, and a golf course for guests' enjoyment. Located 4.8 km from Claude Moore Park, this Herndon villa provides Wi-Fi and a private parking lot.
The Dulles Executive Resort Near Dulles Airport With Private Office
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Terrace
The Dulles Executive Resort Near Dulles Airport With Private Office
Nestled about a 10-minute ride from ArtInsights Gallery of Film and Contemporary Art, the 1-bedroom The Dulles Executive Resort Near Dulles Airport With Private Office Herndon villa is boasting a terrace, a shared lounge, and a golf course for guests' enjoyment. Located 4.8 km from Claude Moore Park, this Herndon villa provides Wi-Fi and a private parking lot.
Spacious 5Br 3Ba Free Parking Minutes To Dc With Pool
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Patio
Situated 3.9 km from Riverbend Park, the 5-bedroom Spacious 5Br 3Ba Free Parking Minutes To Dc With Pool Great Falls villa provides access to numerous tourist attractions in the area.
Spacious 5Br 3Ba Free Parking Minutes To Dc With Pool
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Patio
Spacious 5Br 3Ba Free Parking Minutes To Dc With Pool
Situated 3.9 km from Riverbend Park, the 5-bedroom Spacious 5Br 3Ba Free Parking Minutes To Dc With Pool Great Falls villa provides access to numerous tourist attractions in the area.
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Great deal
Hygge, Upscale & Relaxing Luxury
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Sauna
- Sun terrace
Situated about a 10-minute ride from Greenbriar Local Park, the 5-bedroom Hygge, Upscale & Relaxing Luxury Villa Potomac offers guests to enjoy a sundeck and a golf course. Offering a Jacuzzi and a sauna, this Potomac villa is 2.5 km from the unique Glenstone Museum.
Guests can explore the area with cars offered for rent onsite, where lawn tennis, cycling, and billiard are possible for sport lovers.
Hygge, Upscale & Relaxing Luxury
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Sauna
- Sun terrace
Hygge, Upscale & Relaxing Luxury
Situated about a 10-minute ride from Greenbriar Local Park, the 5-bedroom Hygge, Upscale & Relaxing Luxury Villa Potomac offers guests to enjoy a sundeck and a golf course. Offering a Jacuzzi and a sauna, this Potomac villa is 2.5 km from the unique Glenstone Museum.
Guests can explore the area with cars offered for rent onsite, where lawn tennis, cycling, and billiard are possible for sport lovers.
Cliff'S View Mountain Retreat
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Terrace
Situated 2.7 km from Strickler Knob, Cliff'S View Mountain Retreat Villa Luray entices guests to explore various tourist attractions in the area. This 4-bedroom villa is suitable for up to 10 guests and features a charging station for electric vehicles.
Cliff'S View Mountain Retreat
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Terrace
Cliff'S View Mountain Retreat
Situated 2.7 km from Strickler Knob, Cliff'S View Mountain Retreat Villa Luray entices guests to explore various tourist attractions in the area. This 4-bedroom villa is suitable for up to 10 guests and features a charging station for electric vehicles.
Luxury Home At One Loudoun
- Free parking
- Air conditioning
- Flat-screen TV
- Terrace
Located approximately 5 minutes' walk from One Loudoun, the 1-bedroom Luxury Home At One Loudoun Ashburn offers quick access to various city attractions in the vicinity. The accommodation hosts up to 8 guests and provides them with private parking.
Luxury Home At One Loudoun
- Free parking
- Air conditioning
- Flat-screen TV
- Terrace
Luxury Home At One Loudoun
Located approximately 5 minutes' walk from One Loudoun, the 1-bedroom Luxury Home At One Loudoun Ashburn offers quick access to various city attractions in the vicinity. The accommodation hosts up to 8 guests and provides them with private parking.
Dulles Luxury Movie Theater, Grill, Gazebo
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Luggage storage
- Garden area
Staying at the 6-bedroom Dulles Luxury Movie Theater, Grill, Gazebo Villa Fairfax, guests can easily reach National Air and Space Museum Steven F Udvar Hazy Center, located approximately 6 km away. The Fairfax villa is suitable for up to 16 guests and features private parking.
Dulles Luxury Movie Theater, Grill, Gazebo
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Luggage storage
- Garden area
Dulles Luxury Movie Theater, Grill, Gazebo
Staying at the 6-bedroom Dulles Luxury Movie Theater, Grill, Gazebo Villa Fairfax, guests can easily reach National Air and Space Museum Steven F Udvar Hazy Center, located approximately 6 km away. The Fairfax villa is suitable for up to 16 guests and features private parking.
Villa On The Potomac 2Br Villa
- Flat-screen TV
Staying at Villa On The Potomac 2Br Villa Germantown, guests can visit the Seneca Regional Park, which is nearly a 10-minute drive away.
Villa On The Potomac 2Br Villa
- Flat-screen TV
Villa On The Potomac 2Br Villa
Staying at Villa On The Potomac 2Br Villa Germantown, guests can visit the Seneca Regional Park, which is nearly a 10-minute drive away.
Spacious 10Br 5Ba Free Parking Minutes To Dc With Pool
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Terrace
The 10-bedroom Spacious 10Br 5Ba Free Parking Minutes To Dc With Pool Great Falls villa can host up to 24 guests, boasting a convenient location within 15 minutes' drive of iconic cultural attractions such as the private Glenstone Contemporary Art Museum.
Spacious 10Br 5Ba Free Parking Minutes To Dc With Pool
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Terrace
Spacious 10Br 5Ba Free Parking Minutes To Dc With Pool
The 10-bedroom Spacious 10Br 5Ba Free Parking Minutes To Dc With Pool Great Falls villa can host up to 24 guests, boasting a convenient location within 15 minutes' drive of iconic cultural attractions such as the private Glenstone Contemporary Art Museum.
Luxe-Hot Tub-Game Room-29 Min To Snp-River-5 Acres
- Flat-screen TV
- Tea and coffee facilities
Situated 4.9 km from Valley Star Farm, Luxe-Hot Tub-Game Room-29 Min To Snp-River-5 Acres Goods Mill villa entices guests to explore various tourist attractions in the area.
Luxe-Hot Tub-Game Room-29 Min To Snp-River-5 Acres
- Flat-screen TV
- Tea and coffee facilities
Luxe-Hot Tub-Game Room-29 Min To Snp-River-5 Acres
Situated 4.9 km from Valley Star Farm, Luxe-Hot Tub-Game Room-29 Min To Snp-River-5 Acres Goods Mill villa entices guests to explore various tourist attractions in the area.
Cozy 4Br Retreat - Private Backyard, Gazebo & Grill
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
- Patio
Situated 4.7 km from Braddock Park, the 4-bedroom Cozy 4Br Retreat - Private Backyard, Gazebo & Grill Villa Fairfax entices guests to explore various tourist attractions in the area. This 3-bathroom villa hosts up to 14 guests and provides them with a car park.
Cozy 4Br Retreat - Private Backyard, Gazebo & Grill
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
- Patio
Cozy 4Br Retreat - Private Backyard, Gazebo & Grill
Situated 4.7 km from Braddock Park, the 4-bedroom Cozy 4Br Retreat - Private Backyard, Gazebo & Grill Villa Fairfax entices guests to explore various tourist attractions in the area. This 3-bathroom villa hosts up to 14 guests and provides them with a car park.
Game Rooms & Gym! Luxe Great Falls Estate
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
Staying at Game Rooms And Gym! Luxe Great Falls Estate villa, guests can visit the Lockhouse 22, which is nearly a 10-minute drive away.
Game Rooms & Gym! Luxe Great Falls Estate
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
Game Rooms & Gym! Luxe Great Falls Estate
Staying at Game Rooms And Gym! Luxe Great Falls Estate villa, guests can visit the Lockhouse 22, which is nearly a 10-minute drive away.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Winchester, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Villa Maud |
9.5 / 10 (54 Reviews) |
From 300$ | |
| Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds |
6.7 / 10 (13 Reviews) |
From 368$ | |
| Cozy - Experience It All |
9.8 / 10 (7 Reviews) |
From 156$ | |
| High Meadows Estate |
8.3 / 10 (15 Reviews) |
From 181$ | |
| Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger |
10.0 / 10 (1 Reviews) |
From 1316$ |
More accommodations in Winchester
Frequently Asked Questions
What are the best vacation rentals near downtown Winchester for sightseeing?
Cozy - Experience It All and High Meadows Estate are both located near downtown Winchester. You'll find them convenient for visiting the local shops and attractions.
Start your day early at the historic Loudoun Street to beat the crowds and enjoy breakfast at a local café.
Which vacation rentals near the historic district are ideal for culture lovers?
Villa Maud offers close proximity to the historic district. It's perfect for exploring museums and historic sites.
Visit the Museum of the Shenandoah Valley on a weekday afternoon for a quieter experience.
Are there family-friendly vacation rentals near colleges in Winchester?
Spacious 10Br 5Ba Free Parking Minutes To Dc With Pool accommodates large families and is near Shenandoah University. It's ideal for family functions or campus visits.
Campus tours are more informative when scheduled during open house events, usually held in the spring.
What are some vacation rentals with pools in Winchester for summer fun?
Spacious 5Br 3Ba Free Parking Minutes To Dc With Pool has a lovely pool area. This is great for families looking to cool off during the summer.
Plan pool time before noon to enjoy maximum sun and then explore the city in the cooler afternoons.
Which vacation rentals offer great views of the surrounding nature?
Cliff's View Mountain Retreat features stunning mountain views. It provides a peaceful escape for nature lovers.
Set aside some time for an early morning hike to enjoy the sunrise from the nearby trails.
Are there options for vacation rentals with hot tubs in Winchester?
Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger provides a hot tub experience. Perfect for a relaxing getaway after a day of exploring.
Book your hot tub sessions early evening to enjoy the night sky while you soak.
What are some affordable vacation rentals for families in Winchester?
Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds is budget-friendly and perfect for families. It offers spacious accommodations near outdoor activities.
Visit local parks or hiking spots for free outdoor activities that kids will enjoy.
How can I plan a trip to Winchester centered around seasonal events?
In the winter, the Shenandoah Winter Wine Festival is a must-see. Other events, like the Apple Blossom Festival in spring, offer exciting experiences.
Reserve accommodations early for festivals, especially around the popular Apple Blossom Festival in late April.
What is the easiest way to get around Winchester for activities?
Winchester offers public transportation like buses, but walking is also great for city exploration. Many rentals are centrally located.
Consider biking around the city, as there are many trails that are safer and more scenic than driving.
Is Winchester safe for families traveling with kids?
Winchester is generally safe, but it's wise to stay in well-lit areas at night. Popular tourist joints are well-patrolled.
Stay in neighborhoods that are busy and well-lit, such as near downtown for a sense of security.
Winchester and related destinations