Photo by Nawa Aseen

Winchester Hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 12 - Nov 13
Tomorrow
Nov 13 - Nov 14
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Winchester hotels

Lobby
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 star property
Winchester
7.2 out of 10, Good, (765)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is P4,706
P5,187 total
includes taxes & fees
Nov 23 - Nov 24
Baymont by Wyndham Winchester
Exterior
Value Stay

Value Stay

2.0 star property
Winchester
7.8 out of 10, Good, (123)
"Awesome rooms and service"
United States
Brandon
The price is P3,479
P3,835 total
includes taxes & fees
Dec 1 - Dec 2
Value Stay
Select Comfort beds, in-room safe, desk, laptop workspace
Hampton Inn Winchester

Hampton Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (447)
"Would stay there again"
United States
Patricia
The price is P4,793
P5,284 total
includes taxes & fees
Nov 26 - Nov 27
Hampton Inn Winchester
In-room safe, desk, laptop workspace, blackout drapes
Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

2.5 star property
Winchester
9.2 out of 10, Wonderful, (514)
"Nice room, great staff and just and overall great stay."
United States
Kirk A.
The price is P5,838
P6,436 total
includes taxes & fees
Dec 7 - Dec 8
Holiday Inn Express Lexington East - Winchester by IHG
Desk, iron/ironing board, free WiFi, bed sheets
Comfort Inn Winchester

Comfort Inn Winchester

2.5 star property
Winchester
7.0 out of 10, Good, (349)
" Nice, new facilities"
United States
Francis
The price is P3,959
P4,364 total
includes taxes & fees
Dec 2 - Dec 3
Comfort Inn Winchester
Seasonal outdoor pool
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 star property
Winchester
8.4 out of 10, Very Good, (996)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is P4,761
P5,249 total
includes taxes & fees
Nov 17 - Nov 18
Best Western Winchester Hotel
Exterior
Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East

2.0 star property
Winchester
6.4 out of 10, (581)
"Nice overnight hotel"
United States
Jeffrey Frank
The price is P3,674
P4,050 total
includes taxes & fees
Nov 16 - Nov 17
Red Roof Inn Winchester - Lexington East
Front of property
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 star property
Lexington
9.6 out of 10, Exceptional, (1000)
"Our favorite place to stay when we visit Lexington!"
United States
Allyson
The price is P8,320
P9,657 total
includes taxes & fees
Nov 23 - Nov 24
Origin Lexington a Wyndham Hotel
Lobby
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 star property
Downtown Lexington
8.6 out of 10, Excellent, (1010)
"Convenient location for visiting the area"
United States
Carmen
The price is P7,253
P8,418 total
includes taxes & fees
Nov 28 - Nov 29
Hyatt Regency Lexington
Lobby
Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

3.5 star property
Lexington
8.6 out of 10, Excellent, (1033)
"Location is convienant for my stay."
United States
Marc
The price is P5,613
P6,515 total
includes taxes & fees
Nov 30 - Dec 1
Embassy Suites by Hilton Lexington/UK Coldstream
Snack bar
Tru by Hilton University Medical Center

Tru by Hilton University Medical Center

2.5 star property
South Broadway Park
9.4 out of 10, Exceptional, (531)
"GREAT STAY"
United States
McKenna
The price is P4,786
P5,555 total
includes taxes & fees
Nov 24 - Nov 25
Tru by Hilton University Medical Center
Exterior
GLō Best Western Lexington

GLō Best Western Lexington

3.0 star property
Lexington
9.4 out of 10, Exceptional, (2261)
"Friendly staff, easy check in, very clean and nice room."
United States
Keith
The price is P5,254
P6,098 total
includes taxes & fees
Nov 13 - Nov 14
GLō Best Western Lexington
Lobby
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 star property
Downtown Lexington
8.4 out of 10, Very Good, (1000)
"Great location, friendly staff, great parking. "
United States
Bethany
The price is P7,203
P8,361 total
includes taxes & fees
Nov 30 - Dec 1
Hilton Lexington/Downtown
Lobby
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3.0 star property
Lexington
8.6 out of 10, Excellent, (1207)
"Our stay was really good . Look forward to staying again!"
United States
Connie
The price is P4,717
P5,476 total
includes taxes & fees
Nov 27 - Nov 28
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Property amenity
Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park

2.5 star property
Lexington
9.2 out of 10, Wonderful, (357)
"Excellent room, comfy bed, kind staff"
United States
Juliet
The price is P4,988
P5,789 total
includes taxes & fees
Nov 13 - Nov 14
Everhome Suites Lexington - Horse Park
Lobby
Hyatt Place Lexington

Hyatt Place Lexington

3.0 star property
Lexington
8.8 out of 10, Excellent, (1002)
"The area around the hotel was nice and conveniently located near restaurants. "
United States
Terry-Ann
The price is P5,965
P6,923 total
includes taxes & fees
Nov 13 - Nov 14
Hyatt Place Lexington
Breakfast, lunch, dinner served; southern cuisine
The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4.0 star property
Lexington
8.2 out of 10, Very Good, (1000)
"Staff were great. Room was clean and comfortable. On site restaurant had great options. Welcoming fire going in the foyer fireplace. "
United States
Laura
The price is P5,269
P6,116 total
includes taxes & fees
Nov 24 - Nov 25
The Campbell House Lexington, Curio Collection by Hilton
Lobby
Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg

2.0 star property
Lexington
7.0 out of 10, Good, (1006)
"Would stay again. "
United States
Denise
The price is P3,360
P3,901 total
includes taxes & fees
Nov 19 - Nov 20
Days Inn Lexington SE/Hamburg
Restaurant
The Manchester

The Manchester

4.0 star property
Distillery District
9.6 out of 10, Exceptional, (1041)
"Gorgeous hotel wonderful staff close to everything."
United States
Madeline
The price is P9,503
P12,057 total
includes taxes & fees
Nov 24 - Nov 25
The Manchester
Lobby lounge
Sleep Inn Lexington

Sleep Inn Lexington

2.5 star property
Liberty Area
7.8 out of 10, Good, (800)
"Clean room. Polite and friendly staff. Quite rooms and lots of things to do very close to the hotel. "
United States
Naomi
The price is P4,099
P4,758 total
includes taxes & fees
Dec 10 - Dec 11
Sleep Inn Lexington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Check out family-friendly hotels in Winchester

Seasonal outdoor pool
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 star property
Winchester
8.4 out of 10, Very Good, (996)
The price is P4,761
P5,249 total
includes taxes & fees
Nov 17 - Nov 18
Best Western Winchester Hotel
View all properties

Hotels with a pool in Winchester you'll enjoy

Seasonal outdoor pool
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 star property
Winchester
8.4 out of 10, Very Good, (996)
The price is P4,761
P5,249 total
includes taxes & fees
Nov 17 - Nov 18
Best Western Winchester Hotel
View all properties

These pet-friendly hotels in Winchester may fit your trip

Seasonal outdoor pool
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 star property
Winchester
8.4 out of 10, Very Good, (996)
The price is P4,761
P5,249 total
includes taxes & fees
Nov 17 - Nov 18
Best Western Winchester Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Stay near popular Winchester attractions

Cassell Creek Golf Course

Play a round of golf in Winchester at Cassell Creek Golf Course, and enjoy other activities such as horseback riding. Savor the top-notch restaurants and charming coffeehouses while in town.
See properties

Bluegrass Heritage Museum

You can spend time browsing the exhibits at Bluegrass Heritage Museum during your trip to Winchester. While you're here, you can savor the top-notch restaurants.
See properties

Learn more about Winchester

Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.

See all hotels in Winchester
Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there
Photo by Nawa Aseen
Open Photo by Nawa Aseen

Top Winchester Hotel Reviews

Red Roof Inn Lexington South

Red Roof Inn Lexington South

10/10 Excellent
"Clean and safe. Affordable."
JoDean 3-night trip
Posted 17 hours ago
Red Roof Inn Lexington South

More cheap stays in Winchester

Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2381 Buena Vista Rd, Lexington, KY
The price is P3,491 per night from Nov 19 to Nov 20
P3,491
P4,052 total
Nov 19 - Nov 20
includes taxes & fees
8.6/10 Excellent! (238 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
Holiday Inn Express Lexington East - Winchester by IHG is ranked highly by Expedia customers. This hotel offers free breakfast and an indoor pool. Reviews from our site also recommend Hampton Inn Winchester and Best Western Winchester Hotel as top choices for your visit. See all available top hotels, or vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, the majority of hotel bookings are fully refundable if cancelled before the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, it might still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What's the best place to stay for families in Winchester?
Hampton Inn Winchester is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families. Attractions in the area like Lexington Ice Center and Hummel Planetarium are also fun for kids of all ages. Find more child-friendly accommodations in Winchester.
What is the favorite LGBTQ-friendly accommodation in Winchester?
Holiday Inn Express Lexington East - Winchester by IHG is a top LGBTQ-friendly hotel that features free breakfast and free WiFi. Hampton Inn Winchester and Red Roof Winchester - Lexington East are two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Winchester.
What's the best pet-friendly place to stay in Winchester?
Best Western Winchester Hotel is a top hotel for people traveling with their pets, and offers a seasonal outdoor pool and a computer station for its human guests. Other good choices for you and your pet's trip include Value Stay and Baymont by Wyndham Winchester. See more pet-friendly hotel accommodations in Winchester.
What are some accommodations with pools in Winchester?
Best Western Winchester Hotel is a top hotel with a seasonal outdoor pool, free full breakfast, and free parking. Baymont by Wyndham Winchester is an additional hotel that offers an onsite pool. View all hotels with pools in Winchester.
How is it to stay in Winchester?
Visitors to Winchester are sure to enjoy the restaurants. Tourists can also enjoy the city's coffeehouses, shopping, and football games. A top sight in the area is Kentucky Horse Park. In Winchester, there are 20 hotels and other accommodations to choose from. Find out more about Winchester.
What is there to see in Winchester?
Landmarks like Bluegrass Heritage Museum, Winchester Opera House, and Clark County Courthouse might be worth a visit. Natural beauty is on display at Lykins Park, College Park, and GRCHS Baseball Field. A couple of additional sights to add to your agenda are Southwind Golf Course and Clark County Public Library. Check out what more to see and do in Expedia's Winchester guide.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches.

Explore a world of travel with Expedia