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Top 10 Winchester hotels and places to stay

Our top choices for Winchester hotels

Days Inn Lexington SE/Hamburg

2.0 star property
7.0 out of 10, Good, (1004)
"Great overnight stop "
The price is ฿1,688
฿1,959 total
includes taxes & fees
31 Aug - 1 Sept
Days Inn Lexington SE/Hamburg

Value Stay

2.0 star property
8.0 out of 10, Very good, (92)
"It was right next to the expressway, clean and cheap."
The price is ฿1,912
฿2,108 total
includes taxes & fees
30 Aug - 31 Aug
Value Stay

Super 8 by Wyndham Richmond

2.0 star property
7.6 out of 10, Good, (937)
"The place was fantastic for affordable 1 night stay."
The price is ฿2,042
฿2,251 total
includes taxes & fees
1 Sept - 2 Sept
Super 8 by Wyndham Richmond

Baymont by Wyndham Winchester

2.5 star property
7.2 out of 10, Good, (742)
"Very nice hotel. Staff was wonderful. "
The price is ฿2,162
฿2,384 total
includes taxes & fees
7 Sept - 8 Sept
Baymont by Wyndham Winchester

Quality Inn Lexington -Horse Park

2.5 star property
8.2 out of 10, Very good, (1659)
"Nice overnight stay.slept well "
The price is ฿2,159
฿2,505 total
includes taxes & fees
3 Sept - 4 Sept
Quality Inn Lexington -Horse Park

Best Western Winchester Hotel

2.5 star property
8.4 out of 10, Very good, (965)
"Nice accommodations and very good breakfast. Engaging friendly staff. "
The price is ฿2,917
฿3,216 total
includes taxes & fees
31 Aug - 1 Sept
Best Western Winchester Hotel

Comfort Inn

2.5 star property
7.0 out of 10, Good, (340)
" Nice, new facilities"
The price is ฿2,114
฿2,330 total
includes taxes & fees
21 Sept - 22 Sept
Comfort Inn

Holiday Inn Express Lexington East - Winchester by IHG

2.5 star property
9.4 out of 10, Exceptional, (477)
"Great staff - very friendly!"
The price is ฿3,274
฿3,609 total
includes taxes & fees
21 Sept - 22 Sept
Holiday Inn Express Lexington East - Winchester by IHG

Red Roof Winchester - Lexington East

2.0 star property
6.4 out of 10, (568)
"Staff were really friendly, dog stay free, and the rooms were beautiful"
The price is ฿2,019
฿2,226 total
includes taxes & fees
1 Sept - 2 Sept
Red Roof Winchester - Lexington East

Hampton Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (437)
"Close to Hwy which is nice. Staff friendly. "
The price is ฿4,270
฿4,707 total
includes taxes & fees
31 Aug - 1 Sept
Hampton Inn Winchester

Black Bear Lodge Motel

2.5 star property
8.0 out of 10, Very good, (586)
"Nice accommodations. 👍👍"
The price is ฿2,852
฿3,144 total
includes taxes & fees
8 Sept - 9 Sept
Black Bear Lodge Motel

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3.0 star property
8.8 out of 10, Excellent, (1203)
"Loved the stay. Absolutely would stay again"
The price is ฿2,826
฿3,280 total
includes taxes & fees
2 Sept - 3 Sept
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Home2 Suites By Hilton Richmond, Ky

3.0 star property
9.6 out of 10, Exceptional, (88)
"Enjoyed our stay"
The price is ฿3,831
฿4,224 total
includes taxes & fees
24 Sept - 25 Sept
Home2 Suites By Hilton Richmond, Ky

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1674)
"We were pleased with our stay. Location in the park was great, for a budget friendly place the continental breakfast had a good variety of food options. "
Natural Bridge State Resort Park

GuestHouse Lexington

2.5 star property
8.2 out of 10, Very good, (1334)
"Great place to stay. "
The price is ฿2,077
฿2,411 total
includes taxes & fees
14 Sept - 15 Sept
GuestHouse Lexington

Comfort Inn Lexington I-75

2.5 star property
7.4 out of 10, Good, (684)
"The pool was nice. "
The price is ฿2,176
฿2,526 total
includes taxes & fees
31 Aug - 1 Sept
Comfort Inn Lexington I-75

Super 8 by Wyndham Georgetown

2.0 star property
8.2 out of 10, Very good, (1000)
"We stay at this Super 8 when we go to our sons in Frankfort. We enjoy everything about this hotel"
The price is ฿2,204
฿2,430 total
includes taxes & fees
1 Sept - 2 Sept
Super 8 by Wyndham Georgetown

GLō Best Western Lexington

3.0 star property
9.4 out of 10, Exceptional, (2264)
"Great place to stay!"
The price is ฿2,888
฿3,352 total
includes taxes & fees
1 Sept - 2 Sept
GLō Best Western Lexington

Ramada Limited Mount Sterling

2.0 star property
7.0 out of 10, Good, (735)
"Is a Very Nice place to stay... Staff was Very Friendly and always there for Questions... Walkable to Restaurants..."
The price is ฿2,176
฿2,399 total
includes taxes & fees
21 Sept - 22 Sept
Ramada Limited Mount Sterling

Hotel LEX, Trademark Collection by Wyndham

3.0 star property
8.4 out of 10, Very good, (481)
"Nice hotel, great pool, inviting courtyard and excellent restaurant!"
The price is ฿2,562
฿2,974 total
includes taxes & fees
31 Aug - 1 Sept
Hotel LEX, Trademark Collection by Wyndham
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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Check out hotels with a pool in Winchester

Pet-friendly hotels in Winchester you'll enjoy

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.

Accommodation near Winchester attractions

Shriners Hospitals for Children

Shriners Hospitals for Children

If Shriners Hospitals for Children is what brings you to town, hopefully you'll have a chance to explore more of Lexington.

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.

Photo by Hyelsinta
Open Photo by Hyelsinta

Top Winchester Hotel Reviews

More cheap stays in Winchester

More cheap stays in Winchester

Explore a world of travel with Expedia

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 options 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! 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 Hummel Planetarium 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 Value Stay and Hampton Inn Winchester. 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. A top sight in the area is Kentucky Horse Park. In Winchester, there are 20 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 Lykins Park, College Park and GRCHS Baseball Field. A couple of additional sights to add to your itinerary are Southwind Golf Course and Clark County Public Library. 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.