Photo by Hyelsinta

Winchester Hotels

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Winchester hotels

Comfort Inn

2.5 star property
7.0 out of 10, Good, (335)
"Very clean "
The price is €61
includes taxes & fees
27 Jul - 28 Jul
Comfort Inn

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 €93
includes taxes & fees
6 Jul - 7 Jul
Best Western Winchester Hotel

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 €121
includes taxes & fees
3 Aug - 4 Aug
Hampton Inn Winchester

Holiday Inn Express Lexington East - Winchester by IHG

2.5 star property
9.4 out of 10, Exceptional, (460)
"The hotel staff was super nice and helpful."
The price is €94
includes taxes & fees
3 Aug - 4 Aug
Holiday Inn Express Lexington East - Winchester by IHG

Red Roof Winchester - Lexington East

2.0 star property
6.4 out of 10, (560)
"Staff were really friendly, dog stay free, and the rooms were beautiful"
The price is €58
includes taxes & fees
7 Jul - 8 Jul
Red Roof Winchester - Lexington East

Baymont by Wyndham Winchester

2.5 star property
7.0 out of 10, Good, (712)
"Very nice hotel. Staff was wonderful. "
The price is €71
includes taxes & fees
6 Jul - 7 Jul
Baymont by Wyndham Winchester

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1613)
"Great staff beautiful view!"
Natural Bridge State Resort Park

Black Bear Lodge Motel

2.5 star property
8.2 out of 10, Very good, (548)
"Great stay!"
The price is €79
includes taxes & fees
6 Jul - 7 Jul
Black Bear Lodge Motel

Comfort Inn and Suites

2.5 star property
7.6 out of 10, Good, (633)
"Amazing, love the breakfast and free coffee!!"
The price is €80
includes taxes & fees
3 Aug - 4 Aug
Comfort Inn and Suites

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 €61
includes taxes & fees
3 Aug - 4 Aug
Ramada Limited Mount Sterling

Holiday Inn Express & Suites Mt Sterling North by IHG

2.5 star property
8.8 out of 10, Excellent, (516)
"It was very quiet and staff pleasant. I can stay here again. "
The price is €97
includes taxes & fees
6 Jul - 7 Jul
Holiday Inn Express & Suites Mt Sterling North by IHG

Best Western Paris Inn

2.5 star property
7.8 out of 10, Good, (302)
"Conveniently located in beautiful horse country."
The price is €95
includes taxes & fees
13 Jul - 14 Jul
Best Western Paris Inn

Clarion Pointe Richmond North near University

2.5 star property
8.4 out of 10, Very good, (802)
"The breakfast was better then the usual breakfast you usually get from these type of hotels. The breakfast area felt cozy and modern. "
The price is €67
includes taxes & fees
13 Jul - 14 Jul
Clarion Pointe Richmond North near University

Red Roof Inn Richmond, KY

2.5 star property
7.6 out of 10, Good, (1001)
"It was cool, front desk was nice."
The price is €63
includes taxes & fees
10 Jul - 11 Jul
Red Roof Inn Richmond, KY

Countryside Inn

2.0 star property
5.4 out of 10, (223)
"Very quiet place staff was friendly"
The price is €50
includes taxes & fees
13 Jul - 14 Jul
Countryside Inn

Super 8 by Wyndham Richmond

2.0 star property
7.6 out of 10, Good, (911)
"Check in was fast and courteous."
The price is €52
includes taxes & fees
6 Jul - 7 Jul
Super 8 by Wyndham Richmond

Best Western Richmond Hotel

2.5 star property
7.2 out of 10, Good, (1000)
"Very friendly and respectful"
The price is €64
includes taxes & fees
14 Jul - 15 Jul
Best Western Richmond Hotel

Days Inn by Wyndham Richmond

2.0 star property
5.6 out of 10, (296)
"Nice good place to rest comfortably bed’s friendly staff"
The price is €48
includes taxes & fees
6 Jul - 7 Jul
Days Inn by Wyndham Richmond

Quality Inn Richmond

2.5 star property
8.8 out of 10, Excellent, (1001)
"Nice location!"
The price is €88
includes taxes & fees
6 Jul - 7 Jul
Quality Inn Richmond

Home2 Suites By Hilton Richmond, Ky

3.0 star property
9.6 out of 10, Exceptional, (57)
"Enjoyed our stay"
The price is €102
includes taxes & fees
13 Jul - 14 Jul
Home2 Suites By Hilton Richmond, Ky
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.
Save an average of 15% on thousands of hotels when you're signed in

Hotels with a pool in Winchester you'll enjoy

Hotels with a spa in Winchester may fit your trip

Check out family-friendly hotels 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

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

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.

What are some of the best holiday rentals that Winchester has to offer?

WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!: This holiday home rental outside of Winchester is located in the mountains, and has a selection of games, 1 hot tub and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. See all 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.

What's the most popular hotel in Winchester with an on-site water park or a water park nearby?

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min. is a favourite water park hotel 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.