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$110

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Check availability on Winchester Luxury Hotels

Tonight
15 Aug - 16 Aug
Tomorrow
16 Aug - 17 Aug
Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug

Our top choices for Winchester luxury hotels

Breakfast and dinner served
Exterior
Two Room Suite, 1 King Bed with Sofa Bed, Balcony Interior View
Lobby

1. DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington
Lexington
  • Lexington hotel provides luxurious suites, serene outdoor pool, and upscale dining in the business district.
NZ$210
includes taxes & fees
30 Aug - 31 Aug
DoubleTree Suites by Hilton Hotel Lexington
Terrace/patio
View from property
Lobby
Lounge

2. 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$264
includes taxes & fees
6 Sept - 7 Sept
Marriott Lexington Griffin Gate Golf Resort & Spa
Interior entrance
2 bars/lounges
Rooftop terrace
Penthouse (The Penthouse Suite)

3. The Manchester

The Manchester
Distillery District
NZ$341
includes taxes & fees
7 Sept - 8 Sept
The Manchester
Interior
Property entrance
Lobby sitting area
Bar (on property)

4. 21c Museum Hotel Lexington

21c Museum Hotel Lexington
Downtown Lexington
  • Museum-inspired luxury hotel in city centre Lexington features art in sophisticated spaces near Rupp Arena.
NZ$221
includes taxes & fees
14 Sept - 15 Sept
21c Museum Hotel Lexington
Serves dinner and happy hour
Serves dinner and happy hour
Terrace/patio
Serves dinner and happy hour

5. The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton
Lexington
NZ$218
includes taxes & fees
6 Sept - 7 Sept
The Campbell House Lexington, Curio Collection by Hilton
Exterior detail
Superior Suite, Multiple Beds (Family Two Room Suite King / 2 Twins)
Exterior
Lounge

6. Elwood Hotel & Suites

Elwood Hotel & Suites
Lexington
NZ$216
includes taxes & fees
23 Aug - 24 Aug
Elwood Hotel & Suites
House (0 Bedroom) | Interior
House (0 Bedroom) | Interior
House (0 Bedroom) | Front of property
House (0 Bedroom) | Interior

7. Retro Studio: Romantic Getaway in Frenchburg

Retro Studio: Romantic Getaway in Frenchburg
Frenchburg
NZ$517
includes taxes & fees
16 Aug - 17 Aug
Retro Studio: Romantic Getaway in Frenchburg
View all properties

Top Winchester Hotel Reviews

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

10/10 Excellent
"Great"
Katarina 4-night trip
Posted 10 hours ago
DoubleTree Suites by Hilton Hotel Lexington
Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Excellent stay at this remodeled, non chain hotel, conveniently located and with free parking. Beds and lines are of a high quality, large room, wide selection of foods for breakfast (not included in the room price), very friendly personnel. Keep in mind that AC unit is rather loud. A writing desk in the room would be nice."
natalya 2-night trip
Posted 3 days ago
Elwood Hotel & Suites

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, Winchester Opera House and Clark County Courthouse. If you have extra time while you're in the area, you might want to see College Park and Clark County Public Library.

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