Taos Valley Accommodations - Vacation Rentals in Winchester

Family Retreat w/Deck Near Appalachian Trail! From US $390
         

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10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Security/Safety
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger From US $914
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Historical Paris Cabin on Farm w/Fire Pit! From US $401
         

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10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • View
Shenandoah Thunder Chalet Guest Suite From US $249
         

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9.7 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • View
King Bed Farmhouse Valley Views From US $194
         

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9.7 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Mountain Home Bed & Breakfast From US $151
         

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9.5 (209 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
The VUE - On Top of Paradise From US $271
         

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9.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Front Royal Retreat ~ 1 Mi to National Park! From US $324
         

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9.0 (1 Review)
House
  • Parking
  • Security/Safety
  • Fireplace/Heating

Luxury Places to Stay in Winchester

Over 73+ Luxury Places to Stay in or Near Winchester
Nature Escape Pond Dock Fire Pit Trails From US $828
         

New
House
  • Air Conditioner
  • View
  • Security/Safety
Bend of Brothers River Retreat From US $717
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
High Meadows Estate From US $680
         

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8.3 (16 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Nature Escape - Pond, Dock, Fire Pit, Trails From US $635
         

Sunset Haven From US $519
         

New
Ski Chalet
  • Air Conditioner
  • Parking
  • Pet Friendly
Skycrest Cabin - Sleep in the clouds From US $502
         

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New
House
  • Parking
  • Transportation/Shuttle
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Winchester

Over 26+ Top-Rated Vacation Rentals with a Pool in or Near Winchester
Hampton Inn Winchester From US $108
         

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9.2 (392 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
SpringHill Suites Winchester From US $128
         

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9.2 (252 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The George Washington - A Wyndham Grand Hotel From US $199
         

Tru By Hilton Winchester, Va From US $147
         

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9.0 (349 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Pool
Holiday Inn Winchester Southeast-Historic Gateway by IHG From US $124
         

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9.0 (307 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Holiday Inn Express and Suites Winchester by IHG From US $156
         

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9.0 (164 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
La Quinta by Wyndham Winchester From US $106
         

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8.9 (1778 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hampton Inn Front Royal From US $129
         

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8.9 (500 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Winchester

Over 31+ Pet-Friendly Vacation Rentals in or Near Winchester
Chic Front Royal Retreat Near Shenandoah River! From US $173
         

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8.6 (5 Reviews)
House
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Modern Mountain Retreat w/Deck + Hot Tub! From US $200
         

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8.5 (4 Reviews)
House
  • Parking
  • Pet Friendly
  • Security/Safety
Front Royal Retreat on 3 Acres w/Mtn Views! From US $286
         

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8.5 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Security/Safety
Shenandoah mountain cottage w hot tub & fire pit From US $169
         

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7.2 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Valley Vista-Mins to SkylineDrive-Hot Tub-King, Queen Beds From US $327
         

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6.8 (13 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Stonefire pizza oven frisbee golf and pond From US $339
         

Large Vacation Homes & Villas in Winchester

Over 2+ Large Vacation Homes & Villas in or Near Winchester
Modern Log House First Level Primary From US $241
         

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New
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Big bright family home in town From US $180
         

New
House
  • Air Conditioner
  • Parking
  • Security/Safety

Wheelchair Accessible Vacation Homes in Winchester

Over 18+ Wheelchair Accessible Vacation Homes in or Near Winchester
“Prima” From US $241
         

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New
House
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
TownePlace Suites Winchester From US $142
         

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9.3 (78 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Microtel Inn & Suites by Wyndham Winchester From US $101
         

8.7 (1061 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hilton Garden Inn Winchester From US $138
         

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8.7 (112 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Home2 Suites By Hilton Winchester From US $116
         

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8.7 (9 Reviews)
Hotel
  • Pool
  • Designated Smoking Area
  • Wheelchair Accessible
Doubletree By Hilton Front Royal Blue Ridge Shadows From US $200
         

Holiday Inn Express Stephens City by IHG From US $116
         

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8.5 (154 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Country Inn & Suites by Radisson, Winchester, VA From US $107
         

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8.4 (1167 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Winchester Vacation Rentals and Airbnb Places to Stay Under $200

Over 27+ Winchester Vacation Rentals and Airbnb Places to Stay Under $200
The Queen of Winchester From US $187
         

7.0 (1 Review)
Apartment
  • Parking
  • Security/Safety
  • Child Friendly
Cozy Front Royal Apt, 2 Mi to Skyline Caverns From US $148
         

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New
Apartment
  • Parking
  • Accessibility
  • Security/Safety
Sean's Bar - Private Apartment From US $146
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Buena Vista From US $147
         

New
Other
  • Air Conditioner
  • Parking
  • Security/Safety
Quality Inn Winchester From US $93
         

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8.9 (438 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Child Friendly
TownePlace Suites by Marriott Front Royal From US $166
         

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8.8 (150 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Spark By Hilton Winchester From US $120
         

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8.7 (320 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

About Winchester Vacation Rentals

With more than 82 Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Taos Valley and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Winchester.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Taos Valley Winchester, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Winchester. Places to stay near Winchester are 1586.77 ft² on average, with prices averaging US $251 a night.

Taos Valley makes it easy and safe to find and compare vacation rentals in Winchester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Winchester

Type Count
Hotels 41
Vacation Homes 28
Holiday Apartments 6
Villas 4
B&B 1
Others 1
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Winchester

Pro Tip: Taos Valley makes it easy to compare the best listings on Taos Valley homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Taos Valley homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winchester.

Weather in Winchester

View the weather forecast for Winchester before booking your Winchester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Winchester Vacation Rental Frequently Asked Questions

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:

How many vacation rentals are available in Winchester?

Currently, the total number of properties listed in 2026 is over 82 in the Winchester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Winchester.