Winchester
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Winchester

Apr 21 - Apr 22 ·
2 guests

Winchester Vacation Rentals

Winchester
2 guests

Adults:

2

Children:

0

Child’s age:

Over 35 stays assessed to highlight the standout picks
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Best Winchester Vacation Rentals

Navigation

1. Villa Maud

2. Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds

3. Cozy - Experience It All

4. High Meadows Estate

5. Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger

6. The Dulles Executive Resort Near Dulles Airport With Private Office

7. Spacious 5Br 3Ba Free Parking Minutes To Dc With Pool

8. Hygge, Upscale & Relaxing Luxury

9. Cliff'S View Mountain Retreat

10. Luxury Home At One Loudoun

Vacation rentals near Winchester

These options match your search but are within a one-hour drive of the city (up to 80 km / 50 mi).

  • Guest favorite
Hotel Image Hotel Image

Villa Maud

36450 Philomont Road
38.9 km (24.1 mi) from Winchester
  • In-room breakfast
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Golf centre
  • Sun terrace

Located 2.8 km from Snicker's Gap Turnpike, Villa Maud Middleburg offers karaoke for guests' entertainment.

For a perfect retreat, the property includes a private pool, as well as a Jacuzzi. A terrace is available on site, and hiking and horseback riding can be enjoyed within proximity of this Middleburg accommodation.

9.1
62 reviews
~ US$300 / night

Villa Maud

38.9 km (24.1 mi) from Winchester
  • 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, Villa Maud Middleburg offers karaoke for guests' entertainment.

For a perfect retreat, the property includes a private pool, as well as a Jacuzzi. A terrace is available on site, and hiking and horseback riding can be enjoyed within proximity of this Middleburg accommodation.

9.1
62 reviews
Average price US$ 300 / night
Hotel Image Hotel Image

Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds

515 Corron Drive
29.7 km (18.5 mi) from Winchester
37
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Jacuzzi
  • Sun terrace

Situated 3.2 km from the Skyline Caverns, Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds Front Royal villa offers a Jacuzzi for additional relaxation.

8
12 reviews
~ US$368 / night

Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds

29.7 km (18.5 mi) from Winchester
37
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Jacuzzi
  • Sun terrace

Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds

Situated 3.2 km from the Skyline Caverns, Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds Front Royal villa offers a Jacuzzi for additional relaxation.

8
12 reviews
Average price US$ 368 / night
Popular Vacation rentals destinations
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Cozy - Experience It All

45.6 km (28.3 mi) from Winchester
88
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Tea and coffee facilities

Staying at the 2-bedroom Cozy - Experience It All Berkeley Springs villa, guests can visit Berkeley Springs Brewing Co, which is about a 10-minute ride away.

9.5
4 reviews
~ US$156 / night

Cozy - Experience It All

45.6 km (28.3 mi) from Winchester
88
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Tea and coffee facilities

Cozy - Experience It All

Staying at the 2-bedroom Cozy - Experience It All Berkeley Springs villa, guests can visit Berkeley Springs Brewing Co, which is about a 10-minute ride away.

9.5
4 reviews
Average price US$ 156 / night
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High Meadows Estate

18777 Blue Ridge Mountain Road
28.2 km (17.5 mi) from Winchester
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Heating
  • Terrace
  • Garden area

High Meadows Estate Villa Purcellville is located 2.7 km from the Great Country Farms and welcomes its guests to enjoy diving, canoeing, and horse riding.

8.6
15 reviews
~ US$181 / night

High Meadows Estate

28.2 km (17.5 mi) from Winchester
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Heating
  • Terrace
  • Garden area

High Meadows Estate

High Meadows Estate Villa Purcellville is located 2.7 km from the Great Country Farms and welcomes its guests to enjoy diving, canoeing, and horse riding.

8.6
15 reviews
Average price US$ 181 / night
  • Top location
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Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger

540 Bragg Drive
26.6 km (16.5 mi) from Winchester
123
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Jacuzzi
  • Terrace

Situated 18 minutes' walk from the Deer Lake, the 2-bedroom Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger Villa Front Royal entices guests to explore various tourist attractions in the area.

10
1 reviews
~ US$1316 / night

Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger

26.6 km (16.5 mi) from Winchester
123
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Jacuzzi
  • Terrace

Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger

Situated 18 minutes' walk from the Deer Lake, the 2-bedroom Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger Villa Front Royal entices guests to explore various tourist attractions in the area.

10
1 reviews
Average price US$ 1316 / night
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The Dulles Executive Resort Near Dulles Airport With Private Office

908 Spring Knoll Drive
69.2 km (43.0 mi) from Winchester
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Golf centre
  • Terrace

Boasting a location merely 1.8 km from Chandon Park, The Dulles Executive Resort Near Dulles Airport With Private Office Herndon villa provides a terrace with garden views. This Herndon villa is situated around a 10-minute ride from the Claude Moore Park and boasts yoga instruction for active guests.

10
4 reviews

The Dulles Executive Resort Near Dulles Airport With Private Office

69.2 km (43.0 mi) from Winchester
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Golf centre
  • Terrace

The Dulles Executive Resort Near Dulles Airport With Private Office

Boasting a location merely 1.8 km from Chandon Park, The Dulles Executive Resort Near Dulles Airport With Private Office Herndon villa provides a terrace with garden views. This Herndon villa is situated around a 10-minute ride from the Claude Moore Park and boasts yoga instruction for active guests.

10
4 reviews
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Spacious 5Br 3Ba Free Parking Minutes To Dc With Pool

504 Arnon Meadow Road Unit 1
77.8 km (48.3 mi) from Winchester
279
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Tea and coffee facilities
  • Patio

Located 3.9 km from Riverbend Park, Spacious 5Br 3Ba Free Parking Minutes To Dc With Pool Great Falls villa gives access to various tourist sites in the vicinity.

8
1 reviews
~ US$553 / night

Spacious 5Br 3Ba Free Parking Minutes To Dc With Pool

77.8 km (48.3 mi) from Winchester
279
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Tea and coffee facilities
  • Patio

Spacious 5Br 3Ba Free Parking Minutes To Dc With Pool

Located 3.9 km from Riverbend Park, Spacious 5Br 3Ba Free Parking Minutes To Dc With Pool Great Falls villa gives access to various tourist sites in the vicinity.

8
1 reviews
Average price US$ 553 / night
  • Great deal
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Hygge, Upscale & Relaxing Luxury

13128 Brushwood Way
77.6 km (48.2 mi) from Winchester
883
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Sauna
  • Sun terrace

During the stay at Hygge, Upscale & Relaxing Luxury Villa Potomac, guests can indulge in lawn tennis, cycling, and ping-pong or visit Greenbriar Local Park, located about a 10-minute drive away. Featuring a hot tub and a sauna, the Potomac villa is 2.5 km from the unique Glenstone Museum.

10
1 reviews

Hygge, Upscale & Relaxing Luxury

77.6 km (48.2 mi) from Winchester
883
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Sauna
  • Sun terrace

Hygge, Upscale & Relaxing Luxury

During the stay at Hygge, Upscale & Relaxing Luxury Villa Potomac, guests can indulge in lawn tennis, cycling, and ping-pong or visit Greenbriar Local Park, located about a 10-minute drive away. Featuring a hot tub and a sauna, the Potomac villa is 2.5 km from the unique Glenstone Museum.

10
1 reviews
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Cliff'S View Mountain Retreat

175 Paradise Lane
65.4 km (40.6 mi) from Winchester
260
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Terrace

Located 2.7 km from the Strickler Knob, Cliff'S View Mountain Retreat Villa Luray gives access to various tourist sites in the vicinity.

10
1 reviews

Cliff'S View Mountain Retreat

65.4 km (40.6 mi) from Winchester
260
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Terrace

Cliff'S View Mountain Retreat

Located 2.7 km from the Strickler Knob, Cliff'S View Mountain Retreat Villa Luray gives access to various tourist sites in the vicinity.

10
1 reviews
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Luxury Home At One Loudoun

20497 Milbridge Terrace
63.2 km (39.3 mi) from Winchester
237
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Terrace

Situated approximately 5 minutes' walk from the One Loudoun, Luxury Home At One Loudoun Ashburn offers easy access to numerous tourist spots in the area. Located 2.6 km from Ray Muth Sr. Memorial Park, this Ashburn villa provides Wi-Fi and free private parking.

9
1 reviews

Luxury Home At One Loudoun

63.2 km (39.3 mi) from Winchester
237
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Terrace

Luxury Home At One Loudoun

Situated approximately 5 minutes' walk from the One Loudoun, Luxury Home At One Loudoun Ashburn offers easy access to numerous tourist spots in the area. Located 2.6 km from Ray Muth Sr. Memorial Park, this Ashburn villa provides Wi-Fi and free private parking.

9
1 reviews
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Dulles Luxury Movie Theater, Grill, Gazebo

4016 Maureen Lane
75.0 km (46.6 mi) from Winchester
325
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Luggage storage
  • Garden area

Staying at 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.

7
1 reviews

Dulles Luxury Movie Theater, Grill, Gazebo

75.0 km (46.6 mi) from Winchester
325
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Luggage storage
  • Garden area

Dulles Luxury Movie Theater, Grill, Gazebo

Staying at 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.

7
1 reviews
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Villa On The Potomac 2Br Villa

15415 Seneca Road
73.6 km (45.7 mi) from Winchester
111
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Terrace

Staying at Villa On The Potomac 2Br Villa Germantown, guests can visit the Seneca Regional Park, which is nearly a 10-minute drive away.

5.5
2 reviews

Villa On The Potomac 2Br Villa

73.6 km (45.7 mi) from Winchester
111
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Terrace

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.

5.5
2 reviews
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Spacious 10Br 5Ba Free Parking Minutes To Dc With Pool

504 Arnon Meadow Road
77.8 km (48.3 mi) from Winchester
783
  • Flat-screen TV
  • Tea and coffee facilities

Located about 10 minutes' drive from the Difficult Run Stream Valley Park, Spacious 10Br 5Ba Free Parking Minutes To Dc With Pool Great Falls villa offers a terrace with views of the garden.

~ US$908 / night

Spacious 10Br 5Ba Free Parking Minutes To Dc With Pool

77.8 km (48.3 mi) from Winchester
783
  • Flat-screen TV
  • Tea and coffee facilities

Spacious 10Br 5Ba Free Parking Minutes To Dc With Pool

Located about 10 minutes' drive from the Difficult Run Stream Valley Park, Spacious 10Br 5Ba Free Parking Minutes To Dc With Pool Great Falls villa offers a terrace with views of the garden.

Average price US$ 908 / night
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Luxe-Hot Tub-Game Room-29 Min To Snp-River-5 Acres

151 Fort Liscomb Rd
52.8 km (32.8 mi) from Winchester
223
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Jacuzzi
  • Garden area

Nestled 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 destinations nearby. The villa offers guests a relaxing experience with a Jacuzzi.

Luxe-Hot Tub-Game Room-29 Min To Snp-River-5 Acres

52.8 km (32.8 mi) from Winchester
223
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Jacuzzi
  • Garden area

Luxe-Hot Tub-Game Room-29 Min To Snp-River-5 Acres

Nestled 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 destinations nearby. The villa offers guests a relaxing experience with a Jacuzzi.

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Cozy 4Br Retreat - Private Backyard, Gazebo & Grill

4337 Mt Carriage Ln
75.8 km (47.1 mi) from Winchester
186
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Situated 4.7 km from Braddock Park, Cozy 4Br Retreat - Private Backyard, Gazebo & Grill Villa Fairfax entices guests to explore various tourist attractions in the area.

Cozy 4Br Retreat - Private Backyard, Gazebo & Grill

75.8 km (47.1 mi) from Winchester
186
  • 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, Cozy 4Br Retreat - Private Backyard, Gazebo & Grill Villa Fairfax entices guests to explore various tourist attractions in the area.

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Game Rooms And Gym! Luxe Great Falls Estate

9722 Arnon Chapel Rd
78.4 km (48.7 mi) from Winchester
1000
  • Cookware/ Kitchen utensils
  • Car park
    Charges may apply
  • Flat-screen TV
  • Ironing facilities
  • Heating
  • Fitness centre

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 And Gym! Luxe Great Falls Estate

78.4 km (48.7 mi) from Winchester
1000
  • Cookware/ Kitchen utensils
  • Car park
    Charges may apply
  • Flat-screen TV
  • Ironing facilities
  • Heating
  • Fitness centre

Game Rooms And 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

9.1 / 10

(62 Reviews)

From 300$
Valley Vista-Mins To Skylinedrive-Hot Tub-King, Queen Beds

8.0 / 10

(12 Reviews)

From 368$
Cozy - Experience It All

9.5 / 10

(4 Reviews)

From 156$
High Meadows Estate

8.6 / 10

(15 Reviews)

From 181$
Skyline Yurt: Hot Tub~Wood Stove~Wifi~Evcharger

10.0 / 10

(1 Reviews)

From 1316$

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108 reviews
~ US$ 142 / night
Candlewood Suites Winchester By Ihg Candlewood Suites Winchester By Ihg Candlewood Suites Winchester By Ihg
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~ US$ 109 / night

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