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May 15 - May 16
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May 16 - May 17
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May 17 - May 19
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May 24 - May 26

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Top hotels and accommodation in Winchester

Property grounds
Cozy Mountainside Glamping - Near Red River Gorge (#2)
10.0 out of 10, Exceptional, (5)
"We loved it! We were given ample resources and we had beautiful view. Our host was nice and communicative!"
Cozy Mountainside Glamping - Near Red River Gorge (#2)
Exterior
Sunset Ridge ~ Rustic & Tranquil 100-Acre Getaway!
10.0 out of 10, Exceptional, (14)
"Very peaceful and quite. We enjoyed sitting outside on the porch! A nice place to stay."
The price is NZ$297
per night
19 May - 20 May
Sunset Ridge ~ Rustic & Tranquil 100-Acre Getaway!
Outdoor dining
Luxury on Main / North
10.0 out of 10, Exceptional, (75)
"My sister and I stayed here on a vacation and loved the apartment. It was decorated beautifully and lots of space. We would definitely stay here again."
The price is NZ$293
per night
16 May - 17 May
Luxury on Main / North
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Pool
~4~ Cost Effective Inn by the Red River Gorge
10.0 out of 10, Exceptional, (17)
"Clean place and comfortable beds. Very well kept by the owners. Right off the highway which was convenient (little bit of highway noise though). Close to the Red River Gorge which was nice."
~4~ Cost Effective Inn by the Red River Gorge
Interior
Hot Tub, WiFi, Pet-Friendly - Cozy Tiny Cabin - The Ridge at Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (46)
"This place was absolutely AMAZING....beautiful private and so so peaceful....if you are looking for a secluded little get away this is it....we loved this place....its so super cute and has everything you would need....the hot tub was a delight as well...."
The price is NZ$340
per night
20 May - 21 May
Hot Tub, WiFi, Pet-Friendly - Cozy Tiny Cabin - The Ridge at Red River Gorge, Kentucky!
Suite, 1 King Bed, Non Smoking
Hampton Inn Winchester
2.5 star property
9.4 out of 10, Exceptional, (357)
"Friendly staff very clean comfortable room. Highly recommend staying here."
The price is NZ$262
per night
28 May - 29 May
Hampton Inn Winchester
Exterior
TownePlace Suites by Marriott Richmond
2.5 star property
9.4 out of 10, Exceptional, (252)
"The room was appointed nicely. The front desk was very nice however the woman who checked us in was pretty scary looking with piercings and tattoos displayed provocatively. Not conducive to what I’d expect for Marriott."
The price is NZ$374
per night
3 Jun - 4 Jun
TownePlace Suites by Marriott Richmond
In-room safe, desk, laptop workspace, blackout curtains
Holiday Inn Express Lexington East - Winchester, an IHG Hotel
2.5 star property
9.2 out of 10, Wonderful, (336)
"Property was clean and well appointed with walkable dining options nearby. Breakfast had a nice variety of options. Would stay here again!"
The price is NZ$207
per night
26 May - 27 May
Holiday Inn Express Lexington East - Winchester, an IHG Hotel
Exterior
Holiday Inn Express & Suites Richmond, an IHG Hotel
2.5 star property
9.0 out of 10, Wonderful, (755)
"Very clean and comfortable. Friendly staff"
The price is NZ$232
per night
26 May - 27 May
Holiday Inn Express & Suites Richmond, an IHG Hotel
Premium bedding, in-room safe, iron/ironing board, free cots/infant beds
Hampton Inn Richmond
2.5 star property
9.0 out of 10, Wonderful, (1001)
"Great location off the highway, a few restaurants within walking distance to the hotel. Hotel rooms are clean and comfortable. We have stayed here a few times and it’s always been good. "
The price is NZ$185
per night
27 May - 28 May
Hampton Inn Richmond
Exterior
Quality Inn Richmond
2.5 star property
8.6 out of 10, Excellent, (946)
"Location, newly refurbished, quiet and safe."
The price is NZ$200
per night
19 May - 20 May
Quality Inn Richmond
Reception
Tru by Hilton Richmond
2.5 star property
8.6 out of 10, Excellent, (254)
"This in my opinion is good for 1 night stay, breakfast was good. Coffee was really good. "
Tru by Hilton Richmond
Room, 2 Queen Beds, Non Smoking
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
2.5 star property
8.4 out of 10, Very good, (1521)
"Great staff great stay."
The price is NZ$162
per night
16 May - 17 May
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Exterior
Clarion Pointe Richmond North near University
2.5 star property
8.4 out of 10, Very good, (568)
"The room was clean, the bed was super comfortable, the sheets were soft and clean. What more does one need for an overnight stay?"
The price is NZ$142
per night
26 May - 27 May
Clarion Pointe Richmond North near University
Seasonal outdoor pool
Best Western Winchester Hotel
2.5 star property
8.4 out of 10, Very good, (818)
"This is a great place to stop for the night if you are traveling cross country. We stayed when traveling from DC to St Louis. It's not fancy, but it's clean, quiet, well maintained, and the staff is very friendly. It's even fine for a longer if that's your need. "
The price is NZ$165
per night
19 May - 20 May
Best Western Winchester Hotel
Lobby sitting area
Hotel Lex
2.5 star property
8.0 out of 10, Very good, (111)
"It was nice and clean. Not bathtub in our room. That upset me. "
The price is NZ$213
per night
20 May - 21 May
Hotel Lex
Exterior
Red Roof Inn Richmond, KY
2.5 star property
7.6 out of 10, Good, (848)
"It’s a hotel, it was clean, staff was friendly, breakfast was lacking but good if you need somewhere to sleep."
The price is NZ$133
per night
16 May - 17 May
Red Roof Inn Richmond, KY
Exterior
Super 8 by Wyndham Richmond
2.0 star property
7.6 out of 10, Good, (774)
"The staff was great! My room was clean and accommodating. "
The price is NZ$137
per night
2 Jun - 3 Jun
Super 8 by Wyndham Richmond
Desk, laptop workspace, iron/ironing board, free cots/infant beds
Comfort Suites Richmond
2.5 star property
7.6 out of 10, Good, (594)
"This hotel is clean. Staff is always friendly and helpful. Beds and pillows are very comfortable. Atmosphere feels safe. Never had any problems. We stay here several times per year for business purposes."
The price is NZ$206
per night
19 May - 20 May
Comfort Suites Richmond
Lobby
Comfort Inn Hamburg Area / I-75 Lexington
2.5 star property
7.4 out of 10, Good, (514)
"Very accommodating and very pleasant staff!"
The price is NZ$145
per night
19 May - 20 May
Comfort Inn Hamburg Area / I-75 Lexington
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See all available properties 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.

Frequently asked questions

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 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 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. In Winchester, there are 18 hotels and other accommodation options to choose from. Find out more about Winchester.

What should I do while I'm visiting Winchester?

The picturesque setting of Lykins Park and Community Park exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Bluegrass Heritage Museum and Southwind Golf Course. 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.