An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Luxury Hotels & Resorts in Winchester from NZ$107

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Check availability on Winchester Luxury Hotels

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Winchester luxury hotels

A fire pit with seating and umbrellas in an outdoor area.
A swimming pool with lounge chairs and umbrellas, a clear sky, and a building with a modern design in the background.
A spacious conference room with a long table and chairs, wooden beams on the ceiling, and large windows.
A modern lobby with a central glass fireplace, seating areas, and a high ceiling with natural light.

1. Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa
Lexington
  • Indulge in refined luxury at this Lexington golf resort with spa sanctuary and heated pools.
NZ$263
includes taxes & fees
11 Oct - 12 Oct
Marriott Lexington Griffin Gate Golf Resort & Spa
A hot tub with a view of a forest, a ceiling fan, and a painting on the wall.
A spacious living room with a large sofa, a dining area, and a kitchen.
A modern two-story house with a covered porch and a small tower-like structure on the roof.
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen in the background.

2. New Barndominium/12 Guest /2 Hot Tubs/ 2 Kitchens/ 2 Firepits

New Barndominium/12 Guest /2 Hot Tubs/ 2 Kitchens/ 2 Firepits
Stanton
NZ$1,456
includes taxes & fees
27 Oct - 28 Oct
New Barndominium/12 Guest /2 Hot Tubs/ 2 Kitchens/ 2 Firepits
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Top Winchester Hotel Reviews

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"It was a beautiful hotel & room right in town. Loved our king room so much. The staff was amazing & so friendly. The breakfast was very good. The only issue is the parking. You can park on the street where there’s no open spaces or valet park. So you have to valet park. Daily charge to park plus tipping your valet. They also don’t tell you that up front."
Barry 1-night trip
Posted 1 hour ago
Elwood Hotel & Suites
GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"Over all was a great experience"
Brian 1-night trip
Posted 4 hours ago
GuestHouse Lexington
Hyatt Place Lexington

Hyatt Place Lexington

10/10 Excellent
"Friendly staff, nice hotel, good selection of breakfast items."
Mark 2-night trip
Posted 6 hours ago
Hyatt Place Lexington
Motel 6 Lexington I-75 Hamburg

Motel 6 Lexington I-75 Hamburg

10/10 Excellent
"Very smooth check in process and overall very quiet property. Gas stations directly next to it and stores down the road."
Jeremy 2-night trip
Posted 7 hours ago
Motel 6 Lexington I-75 Hamburg
21c Museum Hotel Lexington

21c Museum Hotel Lexington

10/10 Excellent
"Excellent service!"
GRETCHEN 3-night trip
Posted 18 hours ago
21c Museum Hotel Lexington
Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY

10/10 Excellent
"Great stay- clean and homey! Would def go back!"
Marcy 2-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Georgetown, KY
Microtel Inn by Wyndham Lexington

Microtel Inn by Wyndham Lexington

10/10 Excellent
"This hotel has clean rooms, great staff, and breakfast is pretty good. Parking is good."
Brenda 2-night trip
Posted 2 days ago
Microtel Inn by Wyndham Lexington

Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Winchester?
Use Expedia to help you arrange a flight to Lexington, KY (LEX-Blue Grass) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you'd like to make your stay special. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Winchester offers. During your visit, you might want to enjoy the restaurants which Winchester is known for.
When can I expect good weather in Winchester?
Planning for the weather is an important factor for making your trip to Winchester a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Winchester is 1426 mm.
What's there to see and do in Winchester?
Experience Winchester and visit Bluegrass Heritage Museum, Cassell Creek Golf Course and Winchester Opera House. If you have extra time while you're in the area, you might want to see Clark County Courthouse and College Park.

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