Winchester hotels from RM249

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Check prices for these dates

Tonight
14 Apr - 15 Apr
Tomorrow
15 Apr - 16 Apr
This weekend
17 Apr - 19 Apr
Next weekend
24 Apr - 26 Apr

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Our top choices for Winchester hotels

Lobby

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (461 reviews)
"Clean area all around. Second time staying there. I would stay again for sure. "
United States
Cody
The price is RM517
RM570 total
includes taxes & fees
22 Apr - 23 Apr
Hampton Inn Winchester
Free daily full breakfast

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,002 reviews)
"Room was fine. Fairly clean. King size bed was old."
United States
Heather
The price is RM358
RM394 total
includes taxes & fees
19 Apr - 20 Apr
Best Western Winchester Hotel
Free WiFi, bed sheets

Value Stay

Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (135 reviews)
"Don't let the outside fool you. My room was super clean with brand new appliances..Fast and easy check in, staff was polite. If your looking for a cheap room just to lay your head down you can't go wrong here."
United States
Gary
The price is RM226
RM249 total
includes taxes & fees
16 Apr - 17 Apr
Value Stay
In-room safe, desk, laptop workspace, blackout curtains

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, (557 reviews)
"Clean room, great hot fresh breakfast "
United States
Bob
The price is RM531
RM586 total
includes taxes & fees
10 May - 11 May
Holiday Inn Express Lexington East - Winchester by IHG
Indoor pool

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (785 reviews)
"Great stay and the bed was extremely comfortable "
United States
Kasey
The price is RM300
RM330 total
includes taxes & fees
16 Apr - 17 Apr
Baymont by Wyndham Winchester
Indoor pool

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (360 reviews)
"Very nice "
United States
Ronald
The price is RM275
RM303 total
includes taxes & fees
15 May - 16 May
Comfort Inn Winchester
Exterior

Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (593 reviews)
"Great workers showed us plenty respect clean as a whistle would recommend to anybody"
United States
Kimberly
The price is RM266
RM293 total
includes taxes & fees
22 Apr - 23 Apr
Red Roof Inn Winchester - Lexington East
Living area

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,847 reviews)
"What a great staff Very clean, friendly hotel Def will stay again"
United States
Loreli
The price is RM415
RM457 total
includes taxes & fees
3 May - 4 May
Natural Bridge State Resort Park
Exterior

Black Bear Lodge Motel

Black Bear Lodge Motel
2.5 star property
Slade
8.0 out of 10, Very good, (646 reviews)
"We have stayed here before. It is affordable, the staff is great (I accidently reserved the wrong dates and they were able to fix it and accommodate me on the dates I needed) The area was quiet on this trip as it was out of season. "
United States
Connie
The price is RM349
RM385 total
includes taxes & fees
26 Apr - 27 Apr
Black Bear Lodge Motel
Indoor pool

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (734 reviews)
"Room was very clean, check in was a breeze. "
United States
Emily
The price is RM358
RM395 total
includes taxes & fees
10 May - 11 May
Comfort Inn & Suites Mount Sterling
Lobby sitting area

Ramada Limited Mount Sterling

Ramada Limited Mount Sterling
2.0 star property
Mount Sterling
7.0 out of 10, Good, (805 reviews)
"The mattress was worn out breakfast was subpar and the pool was closed. "
United States
Alan
The price is RM273
RM301 total
includes taxes & fees
30 Apr - 1 May
Ramada Limited Mount Sterling
Exterior

Holiday Inn Express & Suites Mt Sterling North by IHG

Holiday Inn Express & Suites Mt Sterling North by IHG
2.5 star property
Mount Sterling
8.8 out of 10, Excellent, (602 reviews)
"My stay was good."
United States
Gretchen
The price is RM521
RM574 total
includes taxes & fees
3 May - 4 May
Holiday Inn Express & Suites Mt Sterling North by IHG
Exterior

Clarion Pointe Richmond North near University

Clarion Pointe Richmond North near University
2.5 star property
Richmond
8.2 out of 10, Very good, (953 reviews)
"The room was clean, bed was quite comfortable, and the staff was friendly. "
United States
Stephen
The price is RM322
RM355 total
includes taxes & fees
10 May - 11 May
Clarion Pointe Richmond North near University
Desk, blackout curtains, iron/ironing board, free WiFi

Super 8 by Wyndham Richmond

Super 8 by Wyndham Richmond
2.0 star property
Richmond
7.8 out of 10, Good, (1,007 reviews)
"Staff was extremely friendly at check in and check out, and we had a fine stay for a quick overnight "
United States
Laura
The price is RM219
RM242 total
includes taxes & fees
20 Apr - 21 Apr
Super 8 by Wyndham Richmond
Indoor pool

Baymont by Wyndham Richmond KY

Baymont by Wyndham Richmond KY
2.5 star property
Richmond
7.0 out of 10, Good, (1,011 reviews)
"Overall a good stay. Staff was very friendly and helpful "
United States
Wayne
The price is RM280
RM308 total
includes taxes & fees
21 Apr - 22 Apr
Baymont by Wyndham Richmond KY
Exterior

TownePlace Suites by Marriott Richmond

TownePlace Suites by Marriott Richmond
3.0 star property
Richmond
9.4 out of 10, Exceptional, (278 reviews)
"The rooms are always clean and the staff are always amazing!"
United States
Rhett
The price is RM571
RM629 total
includes taxes & fees
26 Apr - 27 Apr
TownePlace Suites by Marriott Richmond
Desk, laptop workspace, iron/ironing board, free cots/infant beds

Comfort Suites Richmond

Comfort Suites Richmond
2.5 star property
Richmond
7.4 out of 10, Good, (736 reviews)
"Comfortable room for the price, hotel in need of refurbishment. "
United States
Graham
The price is RM358
RM395 total
includes taxes & fees
19 Apr - 20 Apr
Comfort Suites Richmond
Interior entrance

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,017 reviews)
"Great stay."
United States
Matthew
The price is RM393
RM433 total
includes taxes & fees
28 Apr - 29 Apr
Quality Inn Richmond
Terrace/patio

Home2 Suites By Hilton Richmond, Ky

Home2 Suites By Hilton Richmond, Ky
3.0 star property
Richmond
9.6 out of 10, Exceptional, (210 reviews)
"Great place to stay close to everything "
United States
Jeannette
The price is RM419
RM462 total
includes taxes & fees
25 Apr - 26 Apr
Home2 Suites By Hilton Richmond, Ky
Indoor pool

Hampton Inn Richmond

Hampton Inn Richmond
2.5 star property
Richmond
9.2 out of 10, Wonderful, (1,011 reviews)
"Wonderful staff, breakfast was great and the room was awesome. "
United States
Cara
The price is RM421
RM464 total
includes taxes & fees
10 May - 11 May
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.
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Stay near popular Winchester attractions

Winchester Traveling Trail

This serene mile-long pathway winds through meadows of Kentucky bluegrass, offering a peaceful escape. Benches and shaded areas make it perfect for a leisurely morning stroll with your leashed dog.
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Bluegrass Heritage Museum

This Romanesque Revival building houses three floors of exhibits chronicling the Bluegrass region's rich heritage. Explore the preserved historic operating room and discover local artefacts spanning centuries.
See properties

Learn more about Winchester

Stroll through charming city centre 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
MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings

Top Winchester Hotel Reviews

The Manchester

The Manchester

10/10 Excellent
"Awesome"
Brad 2-night trip
Posted 4 hours ago
The Manchester

More cheap stays in Winchester

Motel 6 Lexington, KY - Airport

Motel 6 Lexington, KY - Airport

750 Newtown Court Lexington KY
The price is RM214 per night from 26 Apr to 27 Apr
RM214
RM249 total
26 Apr - 27 Apr
includes taxes & fees
6/10 (1,008 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
Holiday Inn Express Lexington Horse Park Area by IHG, located 18.2 mi (29.3 km) from the heart of Winchester, is a top choice for your stay, based on our traveller data. Other good choices for your visit to the area are The Manchester and Elwood Hotel & Suites. 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! You'll find that most hotel room reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a reservation that's non-refundable, you may still be able to cancel 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 family accommodation in Winchester?
Hampton Inn Winchester is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families. Also, attractions in the area such as Lexington Ice Center and Paradise Cove Aquatic Center are fun for children of all ages. Find more child-friendly accommodations in Winchester.
What is the top 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 Wi-Fi. Hampton Inn Winchester and Red Roof Winchester - Lexington East are two other good options for your holiday. See all available hotels listed as LGBTQ-friendly in Winchester.
What's the best dog-friendly accommodation option in Winchester?
Baymont by Wyndham Winchester is a top dog-friendly hotel, and offers an indoor pool and a fitness centre for its human guests. Other good options to stay with your pet include Best Western Winchester Hotel and Value Stay. See more pet-friendly hotel accommodations in Winchester.
What are some accommodation options with pools in Winchester?
Baymont by Wyndham Winchester is a top hotel with a pool, free breakfast and free WiFi. Best Western Winchester Hotel is another choice with an on-site pool. View all hotels with pools in Winchester.
How is it to stay in Winchester?
Visitors to Winchester will definitely enjoy the restaurants. Tourists can also enjoy the city's coffee shops, shopping and football games. In Winchester, there are 21 hotels and other accommodation options to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
Landmarks like Bluegrass Heritage Museum, Winchester Opera House and Clark County Courthouse might be worth a visit. Natural beauty is on display at Winchester Traveling Trail, Lykins Park and College Park. A couple of additional sights to add to your itinerary are Clark County Public Library and GRCHS Baseball Field. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the weather like in Winchester?
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.

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