Androthea Hotel - Vacation Rentals in Winchester

Bedrooms 4, Bathrooms 2, Sleeps 10 From US $405
         

9.2 (27 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger From US $1,999
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
TownePlace Suites by Marriott Front Royal From US $128
         

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9.6 (565 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Secret Gardens Carriage House From US $112
         

9.8 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
The Nest at Chester Gap From US $577
         

10.0 (108 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bedrooms 4, Bathrooms 2, Sleeps 8 From US $365
         

9.2 (29 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Bedrooms 2, Bathrooms 1, Sleeps 4 From US $252
         

8.8 (10 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Winchester

Over 425+ Luxury Places to Stay in or Near Winchester
The Mont Salvat Estate From US $2,033
         

10.0 (33 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Elegant Paris Manor w/Private Pool! From US $1,876
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Tranquil 4-bedroom lodge in Front Royal with AC, WiFi From US $1,655
         

6 Bedroom Farmhouse Owned by Bear Chase From US $1,479
         

10.0 (79 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Breathtaking View with an Indoor Pool From US $1,452
         

9.8 (265 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Winchester

Over 62+ Top-Rated Vacation Rentals with a Pool in or Near Winchester
Ellie's Log Cabin with Beautiful Mountain Views From US $642
         

Whitetail Summit - Shenandoah/hot tub/wineries From US $531
         

9.8 (47 Reviews)
Ski Chalet
  • Air Conditioner
  • Parking
  • Pet Friendly
The George Washington Hotel, A Wyndham Grand Hotel From US $138
         

SpringHill Suites by Marriott Winchester From US $117
         

9.4 (810 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
La Quinta Inn & Suites by Wyndham Winchester From US $123
         

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9.2 (2294 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Microtel Inn & Suites by Wyndham Winchester From US $92
         

Quality Inn Winchester From US $100
         

9.2 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Winchester

Over 194+ Pet-Friendly Vacation Rentals in or Near Winchester
Bedrooms 2, Bathrooms 1, Sleeps 4 From US $252
         

8.6 (8 Reviews)
Cabin
  • Air Conditioner
  • Pet Friendly
  • TV
Historical Paris Cabin on Farm with Fire Pit! From US $405
         

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10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • View
Country Inn & Suites by Radisson, Winchester, VA From US $99
         

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8.8 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Spectacular Cottage with Shenandoah River Views From US $482
         

10.0 (209 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Rolling River Farm: Exquisite Riverfront Paradise From US $533
         

10.0 (123 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Country Elegance overlooking the Shenandoah River From US $547
         

10.0 (110 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Winchester

Over 55+ Large Vacation Homes & Villas in or Near Winchester
Hot tub w/Sunset Views! Secluded mountain chalet From US $404
         

10.0 (42 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Multi-gen Family Mountain House From US $383
         

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9.7 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
New - Modern Mountain Retreat w/Hot tub and view! From US $476
         

10.0 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Summit Hill House with Pond with Mountain Views From US $639
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Highmeadows Estate in the heart of Bluemont Virginia From US $683
         

10.0 (2 Reviews)
Villa
  • Pet Friendly
  • Security/Safety
  • Child Friendly
Spacious 5-bedroom house with WiFi, AC in charming Front Royal From US $242
         

The Royal Cabin | Private Getaway w/Hot Tub From US $783
         

9.8 (11 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Winchester

Over 48+ Wheelchair Accessible Vacation Homes in or Near Winchester
Mountain Home Bed & Breakfast From US $151
         

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9.5 (209 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Comfort Inn & Suites Winchester From US $112
         

9.4 (1094 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
The VUE - On Top of Paradise From US $271
         

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9.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Fairfield Inn & Suites Strasburg Shenandoah Valley From US $126
         

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9.0 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
“Prima” From US $241
         

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New
House
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Hampton Inn Front Royal From US $116
         

9.0 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
TownePlace Suites Winchester From US $142
         

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9.3 (65 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Spark by Hilton Winchester From US $101
         

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9.0 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Winchester Vacation Rentals and Airbnb Places to Stay Under $200

Over 160+ Winchester Vacation Rentals and Airbnb Places to Stay Under $200
City Charmer near Historic OldTown Winchester. From US $138
         

10.0 (60 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Modern Mountain Retreat with Deck and Hot Tub! From US $200
         

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9.7 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Accessibility
Holiday Inn Winchester Se-Historic Gateway by IHG From US $99
         

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9.0 (1006 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Colonial Getaway near Old Town Historic Winchester From US $159
         

New - The Skyline Flat From US $178
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Winchester

Over 207+ Instantly Bookable Vacation Homes in or Near Winchester
Cleveland Park awesome Winchester 2 BR 1st fl napt. walk to everything! From US $289
         

Escape to Shenandoah River, Hot Tub after a Hike! From US $465
         

Beautifully Restored Log Cabin in Bluemont, VA From US $213
         

10.0 (45 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Big Sunny Family House From US $327
         

10.0 (43 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Cozy Bear Chase Cottage From US $367
         

10.0 (41 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Newly renovated Farm cottage with Mountain views From US $324
         

10.0 (40 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

About Winchester Vacation Rentals

With more than 434 Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Androtheahotel 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 Androtheahotel 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 1057.41 ft² on average, with prices averaging $349 a night.

Androtheahotel 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
Vacation Homes 176
Hotels with Suites 85
Cabin Rentals 66
Holiday Apartments 61
Cottages 19
Villas 9
Ski Chalet Rentals 7
Others 5
B&B 1

Use these Quick Filters to Find a Vacation Rental in Winchester

Pro Tip: Androtheahotel makes it easy to compare the best listings on Androtheahotel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Androtheahotel 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?
How many vacation rentals are available in Winchester?

Currently, the total number of properties listed in 2026 is over 434 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.