Airport Express Hotel - Vacation Rentals in Winchester

Holiday Inn Express - Lexington East - Winchester by IHG From US $108
         

Holiday Inn Express Lexington East - Winchester by IHG From US $107
         

Hampton Inn Winchester KY From US $132
         

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7.8 (72 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hampton Inn Winchester From US $115
         

9.2 (449 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Baymont by Wyndham Winchester From US $71
         

7.7 (182 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Best Western Winchester Hotel From US $94
         

8.4 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Best Western Winchester Hotel From US $110
         

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7.6 (213 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Value Stay From US $65
         

7.8 (124 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Accessibility

Luxury Places to Stay in Winchester

Over 28+ Luxury Places to Stay in or Near Winchester
College Park Getaway From US $283
         

8.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Perch - NEW/Downtown! From US $259
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
The Winchester From US $206
         

8.4 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Winchester

Over 2+ Top-Rated Vacation Rentals with a Pool in or Near Winchester
Comfort Inn Winchester From US $68
         

7.0 (351 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn Winchester From US $67
         

6.4 (56 Reviews)
Hotel
  • Parking
  • Pool
  • Private Pool

Pet-Friendly Vacation Rentals in Winchester

Over 13+ Pet-Friendly Vacation Rentals in or Near Winchester
Keystone Sunnydale Mini RV From US $82
         

10.0 (2 Reviews)
RV Rental
  • Air Conditioner
  • Parking
  • Pet Friendly
College Park Getaway From US $174
         

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New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Red Roof Inn Winchester - Lexington East From US $69
         

6.4 (586 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
2nd Story Historic Downtown 2BR with Modern Amenities From US $182
         

9.0 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Wi-Fi - Office Space - Park View Cottage From US $183
         

5.4 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Country getaway From US $232
         

10.0 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Winchester Retreat From US $100
         

9.6 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Winchester

Over 1+ Wheelchair Accessible Vacation Homes in or Near Winchester
Red Roof Inn Winchester - Lexington East From US $62
         

6.7 (114 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Winchester Varoom and Airbnb Places to Stay Under $200

Over 6+ Winchester Varoom and Airbnb Places to Stay Under $200
College Park Bungalow From US $133
         

New
House
  • Air Conditioner
  • Parking
  • TV
College Park Bungalow From US $122
         

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New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
2nd Story Historic Downtown 2BR with Modern Amenities From US $182
         

9.0 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
House with all the amenities From US $175
         

9.4 (13 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Value Stay From US $79
         

6.4 (40 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Perch - NEW/Downtown! From US $186
         

New
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Winchester

Over 1+ Instantly Bookable Vacation Homes in or Near Winchester
NEW Serene Country Refuge at The Right Angle From US $204
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Winchester Vacation Rentals

With more than 14 Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Airportexpresshotel 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 Airportexpresshotel 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 143.97 ft² on average, with prices averaging $88 a night.

Airportexpresshotel 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 with Suites 14

Use these Quick Filters to Find a Vacation Rental in Winchester

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