Photo by Hyelsinta

Find hotels in Winchester, KY from ₩68,269

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
Feb 22 - Feb 23
Tomorrow
Feb 23 - Feb 24
Next weekend
Feb 28 - Mar 2
In two weeks
Mar 7 - Mar 9

Filter by

Guest rating
Guest rating
Star rating

Compare 1,087 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Holiday Inn Express Lexington East - Winchester by IHG
In-room safe, desk, laptop workspace, blackout drapes

Holiday Inn Express Lexington East - Winchester by IHG

2.5 star property
9.2 out of 10, Wonderful, (424)
"Pleasantly nice staff. Jennifer welcomed us with warmth and a smile. I am very happy with everything. The hotel and rooms are very well kept and clean. Thank you!"
The price is ₩149,060
₩165,815 total
includes taxes & fees
Mar 2 - Mar 3
Holiday Inn Express Lexington East - Winchester by IHG
Value Stays by OYO I-64
Exterior

Value Stays by OYO I-64

2.0 star property
8.6 out of 10, Excellent, (51)
"They don't have elevators "
The price is ₩104,801
₩115,522 total
includes taxes & fees
Mar 2 - Mar 3
Value Stays by OYO I-64
Hampton Inn Winchester
Suite, 1 King Bed, Non Smoking | Select Comfort beds, in-room safe, desk, laptop workspace

Hampton Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (411)
"Close to town. "
The price is ₩184,585
₩203,487 total
includes taxes & fees
Mar 23 - Mar 24
Hampton Inn Winchester
Best Western Winchester Hotel
Seasonal outdoor pool

Best Western Winchester Hotel

2.5 star property
8.4 out of 10, Very Good, (893)
"Great place!!!"
The price is ₩121,895
₩134,373 total
includes taxes & fees
Feb 23 - Feb 24
Best Western Winchester Hotel
Baymont by Wyndham Winchester
Lobby

Baymont by Wyndham Winchester

2.5 star property
7.0 out of 10, Good, (647)
"Management was so friendly and supportive "
The price is ₩107,495
₩118,503 total
includes taxes & fees
Feb 23 - Feb 24
Baymont by Wyndham Winchester
Red Roof Winchester - Lexington East
Exterior

Red Roof Winchester - Lexington East

2.0 star property
6.4 out of 10, (534)
"Basic room. Comfy beds. Can’t beat the price. "
The price is ₩81,002
₩89,296 total
includes taxes & fees
Feb 25 - Feb 26
Red Roof Winchester - Lexington East
Natural Bridge State Resort Park
Seasonal outdoor pool

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1496)
"Hiking trail was nice"
The price is ₩123,272
₩135,893 total
includes taxes & fees
Feb 23 - Feb 24
Natural Bridge State Resort Park
Comfort Inn and Suites
Indoor pool

Comfort Inn and Suites

2.5 star property
7.6 out of 10, Good, (575)
"Quiet, affordable, and clean! Highly recommend "
The price is ₩118,797
₩130,962 total
includes taxes & fees
Mar 16 - Mar 17
Comfort Inn and Suites
Ramada Limited Mount Sterling
Lobby sitting area

Ramada Limited Mount Sterling

2.0 star property
6.8 out of 10, (638)
"The hot tub not working 😞"
The price is ₩114,504
₩126,230 total
includes taxes & fees
Feb 27 - Feb 28
Ramada Limited Mount Sterling
Holiday Inn Express & Suites Mt Sterling North by IHG
Exterior

Holiday Inn Express & Suites Mt Sterling North by IHG

2.5 star property
9.0 out of 10, Wonderful, (496)
"It is a nice clean property. Nothing more to add. "
The price is ₩159,200
₩175,507 total
includes taxes & fees
Mar 23 - Mar 24
Holiday Inn Express & Suites Mt Sterling North by IHG
Best Western Paris Inn
Hypo-allergenic bedding, desk, iron/ironing board, rollaway beds

Best Western Paris Inn

2.5 star property
7.8 out of 10, Good, (282)
"It was great. Very friendly staff "
The price is ₩146,179
₩161,142 total
includes taxes & fees
Mar 2 - Mar 3
Best Western Paris Inn
Clarion Pointe Richmond North near University
Exterior

Clarion Pointe Richmond North near University

2.5 star property
8.4 out of 10, Very Good, (688)
"Great check-in, friendly staff. My room was clean, well maintained, and very comfortable. The price was very reasonable for an excellent night's sleep. "
The price is ₩103,554
₩114,158 total
includes taxes & fees
Mar 2 - Mar 3
Clarion Pointe Richmond North near University
Motel 6 Richmond, KY – EKU Campus Area
Standard Room, 1 King Bed, Smoking | Free WiFi

Motel 6 Richmond, KY – EKU Campus Area

2.0 star property
7.2 out of 10, Good, (61)
"The rooms have exterior entry doorways so you do hear the outside traffic. The heater was a little rattley but not to the point that it annoyed us and it worked very well. The room was clean and comfortable. No roaches or bedbugs. Plenty of hot water for the shower. Room also came with a microwave and mini fridge which was nice. It isnt fancy at all but it is affordable and the conditions were nuce for the price. There was no shampoo in room but when i went to front they did have some for...
The price is ₩86,039
₩94,845 total
includes taxes & fees
Feb 23 - Feb 24
Motel 6 Richmond, KY – EKU Campus Area
Red Roof Inn Richmond, KY
Exterior

Red Roof Inn Richmond, KY

2.5 star property
7.6 out of 10, Good, (983)
"Ive stayed multiple times at this location and it in always so clean and the staff are always super nice and helpful "
The price is ₩84,605
₩93,268 total
includes taxes & fees
Feb 23 - Feb 24
Red Roof Inn Richmond, KY
Super 8 by Wyndham Richmond
Exterior

Super 8 by Wyndham Richmond

2.0 star property
7.6 out of 10, Good, (849)
"Very accessible off of Interstate and Cracker Barrel nearby. What more could you ask for. Very pleasant front desk experience at check-in."
The price is ₩80,317
₩88,535 total
includes taxes & fees
Mar 2 - Mar 3
Super 8 by Wyndham Richmond
Best Western Richmond Hotel
Indoor pool

Best Western Richmond Hotel

2.5 star property
7.2 out of 10, Good, (1000)
"The check in was quick and the staff was friendly. The room was clean and parking was good. They are doing updates on the facility, but we had a good stay."
The price is ₩112,142
₩123,626 total
includes taxes & fees
Mar 3 - Mar 4
Best Western Richmond Hotel
Days Inn by Wyndham Richmond
Premium bedding, pillowtop beds, in-room safe, desk

Days Inn by Wyndham Richmond

2.0 star property
5.6 out of 10, (272)
"I haven’t got there yet I need the room for Thursday the 9th of January I need to check in around 10 am no later than 11am "
The price is ₩68,269
₩75,259 total
includes taxes & fees
Feb 24 - Feb 25
Days Inn by Wyndham Richmond
Quality Inn Richmond
Exterior

Quality Inn Richmond

2.5 star property
8.8 out of 10, Excellent, (1001)
"Overnight stay on the way to Gatlinburg. The desk staff were super friendly. The hotel was super clean. Several nearby restaurants and decent breakfast. "
The price is ₩141,989
₩156,532 total
includes taxes & fees
Mar 4 - Mar 5
Quality Inn Richmond
Holiday Inn Express & Suites Richmond by IHG
Exterior

Holiday Inn Express & Suites Richmond by IHG

2.5 star property
9.0 out of 10, Wonderful, (837)
"Room and bathroom were very clean. Breakfast and dining area were also well kept. Good selection of breakfast offered."
The price is ₩169,126
₩186,445 total
includes taxes & fees
Mar 5 - Mar 6
Holiday Inn Express & Suites Richmond by IHG
Hampton Inn Richmond
Premium bedding, in-room safe, iron/ironing board

Hampton Inn Richmond

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Hotel was clean and quiet. "
The price is ₩157,263
₩173,367 total
includes taxes & fees
Mar 16 - Mar 17
Hampton Inn Richmond
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Winchester

Trip time! Discover the local cuisine, hiking, and football in Winchester.

See all hotels in Winchester
Canoeing down the Kentucky river 🚣
Photo by Hyelsinta
Open Photo by Hyelsinta

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 Value Stays by OYO I-64 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.

Where can I learn more about changing or cancelling my trip to Winchester?

For more information about changing or cancelling your trip to Winchester, head over to our customer service page.

What's the best place to stay on a budget in Winchester?

Based on reviews, Red Roof Inn Lexington - Winchester is a popular hotel for our travelers who want a more economical choice, and features free WiFi and free parking. View all budget hotels 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 Explorium 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?

Baymont by Wyndham Winchester is a top dog-friendly hotel, and offers an indoor pool and a fitness center for its human guests. Other good choices for you and your pet's trip include Value Stays by OYO I-64 and Hampton Inn Winchester. See more pet-friendly hotel accommodations in Winchester.

Where is the best hotel to stay close to Community Park?

Best Western Winchester Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and free parking. It's located just a short 0.8 mi (1.3 km) from Community Park. Other good choices within a few miles include Baymont by Wyndham Winchester and Holiday Inn Express Lexington East - Winchester, an IHG Hotel.

What about the best place to stay close to Southwind Golf Course?

One of the top choices for your stay is Best Western Winchester Hotel, located 2.7 mi (4.3 km) from Southwind Golf Course, and this hotel offers free breakfast and free parking. Holiday Inn Express Lexington East - Winchester, an IHG Hotel and Baymont by Wyndham Winchester are two other good choices within 5 miles.

What's the best golf hotel in Winchester?

House on Belmont is a B&B featuring free breakfast and laundry facilities, and it's a top choice for golfing nearby. Visit Southwind Golf Course or Cassell Creek Golf Course to perfect your golf swing. See more golf hotels in Winchester.

What are some accommodations with pools in Winchester?

Baymont by Wyndham Winchester is a top hotel with a pool, free breakfast, and free WiFi. Other choices that feature an onsite pool include Hampton Inn Winchester and Best Western Winchester Hotel. View all hotels with pools in Winchester.

What is the best spa hotel in Winchester?

Baymont by Wyndham Winchester is a top spa hotel featuring a pool and a fitness center. See all spa hotels in Winchester.

What is the best accommodation for staying close to Blue Grass Airport (LEX)?

Chateau Annette is a popular 3.5-star B&B featuring free breakfast and free parking. It's located a short 1.8 mi (3 km) from Blue Grass Airport. Other good choices close to the airport include Comfort Suites and Americas Best Value Inn Blue Grass Airport.

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. In Winchester, there are 19 hotels and other accommodations to choose from. Find out more about Winchester.

What is there to see in Winchester?

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 Bluegrass Heritage Museum and Southwind Golf Course. 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.