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Winchester Hotels from S$73

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Top 10 trending Winchester hotels

Baymont by Wyndham Winchester

2.5 star property
7.0 out of 10, Good, (706)
"Very nice hotel. Staff was wonderful. "
The price is S$106
includes taxes & fees
1 Jul - 2 Jul
Baymont by Wyndham Winchester

Comfort Inn

2.5 star property
7.0 out of 10, Good, (335)
"Very clean "
The price is S$92
includes taxes & fees
27 Jul - 28 Jul
Comfort Inn

Holiday Inn Express Lexington East - Winchester by IHG

2.5 star property
9.4 out of 10, Exceptional, (459)
"The hotel staff was super nice and helpful."
The price is S$163
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn Express Lexington East - Winchester by IHG

Hampton Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (428)
"Easy access to the hotel and drivable distance to other restaurants. Briana is friendly and helpful with the check in process. "
The price is S$198
includes taxes & fees
24 Jul - 25 Jul
Hampton Inn Winchester

Red Roof Winchester - Lexington East

2.0 star property
6.4 out of 10, (559)
"Staff were really friendly, dog stay free, and the rooms were beautiful"
The price is S$88
includes taxes & fees
1 Jul - 2 Jul
Red Roof Winchester - Lexington East

Best Western Winchester Hotel

2.5 star property
8.4 out of 10, Very good, (937)
"best check in staff I have ever experienced. one of the best breakfasts also. Room has a full size jacucci and the pool was open"
The price is S$134
includes taxes & fees
28 Jun - 29 Jun
Best Western Winchester Hotel

Value Stay

2.0 star property
8.2 out of 10, Very good, (74)
"This was a nice, clean, quiet place to stop over on our travels. I would stay here again."
The price is S$87
includes taxes & fees
11 Jul - 12 Jul
Value Stay

Origin Lexington a Wyndham Hotel

3.5 star property
9.6 out of 10, Exceptional, (1000)
"Nice rooms, great restaurant."
The price is S$187
includes taxes & fees
1 Jul - 2 Jul
Origin Lexington a Wyndham Hotel

Embassy Suites by Hilton Lexington/UK Coldstream

3.5 star property
8.6 out of 10, Excellent, (1010)
"Great location, near the highway, and provided an excellent reception and breakfast. "
The price is S$150
includes taxes & fees
6 Jul - 7 Jul
Embassy Suites by Hilton Lexington/UK Coldstream

Hyatt Place Lexington

3.0 star property
8.8 out of 10, Excellent, (1010)
"Breakfast was excellent, room very clean!"
The price is S$141
includes taxes & fees
14 Jul - 15 Jul
Hyatt Place Lexington

Sleep Inn Lexington

2.5 star property
7.8 out of 10, Good, (708)
"We had very nice stay at this hotel. The room was clean, the bed was comfy and the property was quiet. It was easy in and out. We would stay there again."
The price is S$99
includes taxes & fees
4 Jul - 5 Jul
Sleep Inn Lexington

Days Inn Lexington SE/Hamburg

2.0 star property
7.0 out of 10, Good, (961)
"Nice room for our one night stay in Lexington."
The price is S$77
includes taxes & fees
15 Jul - 16 Jul
Days Inn Lexington SE/Hamburg

Hilton Lexington/Downtown

3.5 star property
8.4 out of 10, Very good, (1003)
"Would stay here again. Great choice with close proximity to Rupp Arena. "
The price is S$202
includes taxes & fees
4 Jul - 5 Jul
Hilton Lexington/Downtown

Everhome Suites Lexington - Horse Park

2.5 star property
9.2 out of 10, Wonderful, (246)
"Great stay!"
The price is S$139
includes taxes & fees
1 Jul - 2 Jul
Everhome Suites Lexington - Horse Park

Ramada Limited Mount Sterling

2.0 star property
7.0 out of 10, Good, (704)
"Jaccuzzi in room, nice staff, and nice rooms."
The price is S$92
includes taxes & fees
1 Jul - 2 Jul
Ramada Limited Mount Sterling

Springhill Suites by Marriott Lexington Fritz Farm

3.0 star property
9.4 out of 10, Exceptional, (238)
"Love staying here! Great location, clean, professional and friendly staff."
The price is S$172
includes taxes & fees
6 Jul - 7 Jul
Springhill Suites by Marriott Lexington Fritz Farm

Tru by Hilton University Medical Center

2.5 star property
9.4 out of 10, Exceptional, (360)
"Nice hotel very clean, check in was quick and they had a good selection for breakfast!"
The price is S$141
includes taxes & fees
6 Jul - 7 Jul
Tru by Hilton University Medical Center

Fairfield Inn & Suites by Marriott Lexington North

3.0 star property
8.6 out of 10, Excellent, (1003)
"Rooms were very clean and the spa was just what I needed after a very long days drive. "
The price is S$124
includes taxes & fees
20 Jul - 21 Jul
Fairfield Inn & Suites by Marriott Lexington North

Quality Inn Lexington -Horse Park

2.5 star property
8.2 out of 10, Very good, (1624)
"Staff was friendly, room was clean and quiet. "
The price is S$94
includes taxes & fees
14 Jul - 15 Jul
Quality Inn Lexington -Horse Park

Spark by Hilton Lexington Hamburg

2.5 star property
8.8 out of 10, Excellent, (30)
"Property was nice, room Clean, staff very friendly."
The price is S$95
includes taxes & fees
5 Jul - 6 Jul
Spark by Hilton Lexington Hamburg
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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Family-friendly hotels in Winchester you'll enjoy

These pet-friendly hotels in Winchester may fit your trip

Check out hotels with a pool in Winchester

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.

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

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 Value Stay 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 budget-friendly accommodation in Winchester?

Based on reviews, Red Roof Inn Lexington - Winchester is a popular hotel for our travellers who want a more economical choice, and features free WiFi and free parking. View all budget hotels 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. Best Western Winchester Hotel and Hampton Inn Winchester 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 Best Western Winchester Hotel. See more pet-friendly hotel accommodations in Winchester.

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 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.

What is the best spa hotel in Winchester?

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