Pawleys Island Vacation Rental - Vacation Rentals in Winchester

Bedrooms 4, Bathrooms 2, Sleeps 10 From US $417
         

9.2 (25 Reviews)
Cabin
  • Air Conditioner
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  • Pet Friendly
Luxury 4BR Retreat Kitchen Grill Fireplace From US $279
         

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10.0 (3 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
Secret Gardens Carriage House From US $112
         

9.8 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
The Nest at Chester Gap From US $463
         

10.0 (104 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
Bedrooms 4, Bathrooms 2, Sleeps 8 From US $367
         

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

8.8 (5 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Winchester

Over 395+ Luxury Places to Stay in or Near Winchester
The Mont Salvat Estate From US $2,013
         

10.0 (33 Reviews)
House
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  • Security/Safety
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger From US $1,999
         

10.0 (1 Review)
Villa
  • Air Conditioner
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  • Pet Friendly
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
         

Stunning Bluemont Manor with 9 Bedrooms 7 Baths From US $1,548
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Winchester

Over 65+ Top-Rated Vacation Rentals with a Pool in or Near Winchester
6 Bedroom Farmhouse Owned by Bear Chase From US $875
         

10.0 (78 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
Ellie's Log Cabin with Beautiful Mountain Views From US $493
         

Breathtaking View with an Indoor Pool From US $1,137
         

9.8 (262 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Whitetail Summit - Shenandoah/hot tub/wineries From US $623
         

9.8 (46 Reviews)
Ski Chalet
  • Air Conditioner
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  • Pet Friendly
TownePlace Suites by Marriott Front Royal From US $142
         

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9.6 (554 Reviews)
Hotel
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  • Pool
L'Auberge Provencale Inn & Restaurant From US $310
         

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9.6 (173 Reviews)
Hotel
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  • Pool
The George Washington Hotel, A Wyndham Grand Hotel From US $144
         

Pet-Friendly Vacation Rentals in Winchester

Over 176+ Pet-Friendly Vacation Rentals in or Near Winchester
Pure Luxury From US $259
         

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10.0 (2 Reviews)
House
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  • Pet Friendly
La Quinta Inn & Suites by Wyndham Winchester From US $104
         

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9.2 (2241 Reviews)
Hotel
  • Air Conditioner
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  • Pet Friendly
Spectacular Cottage with Shenandoah River Views From US $463
         

10.0 (209 Reviews)
Cottage
  • Air Conditioner
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  • Pet Friendly
Rolling River Farm: Exquisite Riverfront Paradise From US $477
         

10.0 (121 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Country Elegance overlooking the Shenandoah River From US $568
         

10.0 (106 Reviews)
Cottage
  • Air Conditioner
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  • Pet Friendly
Family Retreat w/Deck Near Appalachian Trail! From US $447
         

10.0 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Winchester

Over 47+ Large Vacation Homes & Villas in or Near Winchester
Hot tub w/Sunset Views! Secluded mountain chalet From US $351
         

10.0 (40 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
Mountain Home Bed & Breakfast From US $151
         

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9.3 (242 Reviews)
Bed & Breakfast
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  • TV
New - Modern Mountain Retreat w/Hot tub and view! From US $475
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Summit Hill House with Pond with Mountain Views From US $604
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious 5-bedroom house with WiFi, AC in charming Front Royal From US $242
         

Wheelchair Accessible Vacation Homes in Winchester

Over 49+ Wheelchair Accessible Vacation Homes in or Near Winchester
TownePlace Suites Winchester From US $107
         

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9.2 (61 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Comfort Inn & Suites Winchester From US $108
         

9.4 (1075 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Hampton Inn Winchester From US $105
         

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9.1 (338 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Microtel Inn & Suites by Wyndham Winchester From US $78
         

La Quinta by Wyndham Winchester From US $106
         

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8.9 (1778 Reviews)
Hotel
  • Air Conditioner
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  • Pet Friendly
Quality Inn Winchester From US $82
         

9.2 (1006 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Tru By Hilton Winchester, Va From US $124
         

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8.9 (370 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Pool
Hampton Inn Winchester N/Conference Center, VA From US $117
         

9.2 (846 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Winchester Varoom and Airbnb Places to Stay Under $200

Over 162+ Winchester Varoom and Airbnb Places to Stay Under $200
City Charmer near Historic OldTown Winchester. From US $129
         

10.0 (60 Reviews)
House
  • Air Conditioner
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  • TV
Apt movie theater game room treadmill From US $150
         

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10.0 (1 Review)
Apartment
  • Parking
  • Security/Safety
  • Child Friendly
Hampton Inn Front Royal From US $110
         

9.0 (1014 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Colonial Getaway near Old Town Historic Winchester From US $170
         

Indigo Blue modern open vibe on tree lined street From US $134
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Shenandoah Mountain House - Guest Suite From US $163
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Winchester

Over 193+ Instantly Bookable Vacation Homes in or Near Winchester
Escape to Shenandoah River, Hot Tub after a Hike! From US $294
         

Cozy Bear Chase Cottage From US $317
         

10.0 (41 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Big Sunny Family House From US $442
         

10.0 (40 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Historic Bluemont Village Home From US $428
         

10.0 (38 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Newly renovated Farm cottage with Mountain views From US $325
         

10.0 (38 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

About Winchester Vacation Rentals

With more than 404 Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Pawleysislandvacationrental 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 Pawleysislandvacationrental 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 1049.41 ft² on average, with prices averaging $335 a night.

Pawleysislandvacationrental 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 160
Hotels with Suites 83
Holiday Apartments 61
Cabin Rentals 57
Cottages 18
Villas 10
Ski Chalet Rentals 7
Others 3
B&B 1

Use these Quick Filters to Find a Vacation Rental in Winchester

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