Yntravel - Vacation Rentals in Winchester

Property Image From US $121
         

10.0 (144 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $576
         

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10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Property Image From US $106
         

8.8 (656 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $394
         

10.0 (88 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $322
         

10.0 (81 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Winchester

Over 262+ Luxury Places to Stay in or Near Winchester
Property Image From US $1,978
         

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New
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $1,620
         

9.6 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From US $1,129
         

Property Image From US $930
         

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9.8 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Property Image From US $879
         

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New
House
  • Air Conditioner
  • Security/Safety
  • Sports/Activities
Property Image From US $823
         

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8.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Accessibility

Top-Rated Vacation Rentals with a Pool in Winchester

Over 66+ Top-Rated Vacation Rentals with a Pool in or Near Winchester
Property Image From US $326
         

10.0 (51 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $345
         

Property Image From US $622
         

10.0 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $331
         

10.0 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $537
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $182
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $583
         

Pet-Friendly Vacation Rentals in Winchester

Over 65+ Pet-Friendly Vacation Rentals in or Near Winchester
Property Image From US $425
         

10.0 (34 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $320
         

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10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $298
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $188
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $226
         

Large Vacation Homes & Villas in Winchester

Over 127+ Large Vacation Homes & Villas in or Near Winchester
Property Image
New
From US $653
         

10.0 (50 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From US $380
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $214
         

Wheelchair Accessible Vacation Homes in Winchester

Over 3+ Wheelchair Accessible Vacation Homes in or Near Winchester
Property Image From US $146
         

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7.6 (125 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $652
         

5.0 (12 Reviews)
House
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace

Winchester Varoom and Airbnb Places to Stay Under $200

Over 54+ Winchester Varoom and Airbnb Places to Stay Under $200
Property Image From US $121
         

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9.4 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $168
         

9.8 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $110
         

9.8 (15 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $127
         

9.6 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Winchester

Over 123+ Instantly Bookable Vacation Homes in or Near Winchester
Property Image From US $528
         

Property Image From US $331
         

Property Image From US $237
         

Property Image From US $276
         

Property Image From US $502
         

10.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Winchester Vacation Rentals

With more than 271 Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Yntravel 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 Yntravel 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 3581 ft² on average, with prices averaging $395 a night.

Yntravel 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 214
Cabin Rentals 28
Holiday Apartments 14
Cottages 6
Hotels with Suites 3
Others 3
Villas 2
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Winchester

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

Complexes around Winchester, TN