Gardenya Hotel - Vacation Rentals in Winchester

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

9.2 (27 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Family Retreat w/Deck Near Appalachian Trail! From US $390
         

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10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Security/Safety
Relax Inn Motel From US $76
         

8.4 (283 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Secret Gardens Carriage House From US $105
         

9.8 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
The Nest at Chester Gap From US $577
         

10.0 (111 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bedrooms 4, Bathrooms 2, Sleeps 8 From US $367
         

9.2 (29 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Bedrooms 2, Bathrooms 1.5, Sleeps 4 From US $253
         

9.0 (6 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Winchester

Over 423+ Luxury Places to Stay in or Near Winchester
The Mont Salvat Estate From US $2,201
         

10.0 (33 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Elegant Paris Manor w/Private Pool! From US $1,983
         

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 $1,382
         

10.0 (80 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool
13 BR Boutique in Berryville From US $1,206
         

7.8 (7 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Skyline Yurt From US $1,114
         

New
House
  • Air Conditioner
  • TV
  • Balcony/Terrace

Top-Rated Vacation Rentals with a Pool in Winchester

Over 63+ Top-Rated Vacation Rentals with a Pool in or Near Winchester
Whitetail Summit - Shenandoah/hot tub/wineries From US $623
         

10.0 (55 Reviews)
Ski Chalet
  • Air Conditioner
  • Parking
  • Pet Friendly
Ellie's Log Cabin with Beautiful Mountain Views From US $642
         

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 $276
         

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

Pet-Friendly Vacation Rentals in Winchester

Over 196+ 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
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger From US $914
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Cleveland Park awesome Winchester 2 BR 1st fl napt. walk to everything! From US $289
         

Spectacular Cottage with Shenandoah River Views From US $592
         

10.0 (210 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Rolling River Farm: Exquisite Riverfront Paradise From US $605
         

10.0 (125 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Country Elegance overlooking the Shenandoah River From US $605
         

10.0 (111 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Beautifully Restored Log Cabin in Bluemont, VA From US $222
         

10.0 (46 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Winchester

Over 54+ Large Vacation Homes & Villas in or Near Winchester
Hot tub w/Sunset Views! Secluded mountain chalet From US $298
         

10.0 (44 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
King Bed Farmhouse Valley Views From US $194
         

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9.7 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Highmeadows Estate in the heart of Bluemont Virginia From US $683
         

10.0 (2 Reviews)
Villa
  • Pet Friendly
  • Security/Safety
  • Sports/Activities
New - Modern Mountain Retreat w/Hot tub and view! From US $502
         

9.8 (31 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Scarborough Fair walk to downtown two story apt From US $395
         

9.8 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Winchester

Over 44+ 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
ANS Inn & Suites From US $74
         

7.4 (69 Reviews)
Hotel
  • 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
“Prima” From US $241
         

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New
House
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
TownePlace Suites by Marriott Front Royal From US $155
         

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9.6 (582 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
TownePlace Suites Winchester From US $142
         

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9.3 (78 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Comfort Inn & Suites Winchester From US $106
         

9.4 (1106 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Winchester Vacation Rentals and Airbnb Places to Stay Under $200

Over 157+ Winchester Vacation Rentals and Airbnb Places to Stay Under $200
Newly renovated Farm cottage with Mountain views From US $199
         

10.0 (43 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Front Royal Studio w/Mtn Views & Brick Oven From US $158
         

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9.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • Security/Safety
Mountain View Bungalow in Front Royal From US $167
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Mountain View Bungalow in Front Royal From US $176
         

10.0 (24 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Apple Mountain Retreat From US $166
         

10.0 (24 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Winchester

Over 209+ Instantly Bookable Vacation Homes in or Near Winchester
Escape to Shenandoah River, Hot Tub after a Hike! From US $465
         

Big Sunny Family House From US $296
         

10.0 (47 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Cozy Bear Chase Cottage From US $365
         

10.0 (44 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi From US $326
         

10.0 (35 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

About Winchester Vacation Rentals

With more than 432 Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Gardenyahotel 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 Gardenyahotel 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 1034.29 ft² on average, with prices averaging US $353 a night.

Gardenyahotel 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 180
Hotels 79
Cabin Rentals 65
Holiday Apartments 63
Cottages 20
Villas 9
Ski Chalet Rentals 7
Others 2
B&B 1

Use these Quick Filters to Find a Vacation Rental in Winchester

Pro Tip: Gardenyahotel makes it easy to compare the best listings on Gardenyahotel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Gardenyahotel 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 432 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.