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Find hotels in Winchester, KY from $55

Check Winchester hotel prices

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May 21 - May 22
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May 22 - May 23
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May 24 - May 26
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May 31 - Jun 2

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Compare 1,210 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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 $132
$180 total
includes taxes & fees
May 29 - May 30
Sunset Ridge ~ Rustic & Tranquil 100-Acre Getaway!
Outdoor dining
Luxury on Main / North
10.0 out of 10, Exceptional, (76)
"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 $90
$176 total
includes taxes & fees
May 25 - May 26
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, (47)
"Quaint peaceful cottage with a great fire pit and hot tub. It was very comfortable and had all the coveniences. MI finca in town for really good mexican food was a plus. We went to RRG underground Kayak and climbed the Natural Bridge in one afternoon so it was so nice to come back to seclusion and relax in the hot tub. We would highly recommend it!!"
The price is $101
$207 total
includes taxes & fees
May 28 - May 29
Hot Tub, WiFi, Pet-Friendly - Cozy Tiny Cabin - The Ridge at Red River Gorge, Kentucky!
Suite, 1 King Bed, Non Smoking | Select Comfort beds, in-room safe, desk, laptop workspace
Hampton Inn Winchester
2.5 star property
9.4 out of 10, Exceptional, (358)
"Friendly staff very clean comfortable room. Highly recommend staying here."
The price is $137
$151 total
includes taxes & fees
Jun 20 - Jun 21
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 $209
$230 total
includes taxes & fees
May 23 - May 24
TownePlace Suites by Marriott Richmond
Premium bedding, in-room safe, iron/ironing board
Hampton Inn Richmond
2.5 star property
9.2 out of 10, Wonderful, (1001)
"Great stay"
The price is $112
$123 total
includes taxes & fees
May 27 - May 28
Hampton Inn Richmond
In-room safe, desk, laptop workspace, blackout drapes
Holiday Inn Express Lexington East - Winchester, an IHG Hotel
2.5 star property
9.2 out of 10, Wonderful, (337)
"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 $89
$99 total
includes taxes & fees
May 26 - May 27
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 $119
$131 total
includes taxes & fees
Jun 16 - Jun 17
Holiday Inn Express & Suites Richmond, an IHG Hotel
Exterior
Quality Inn Richmond
2.5 star property
8.6 out of 10, Excellent, (951)
"Quiet, clean, nicely furnished and the breakfast was better than most competitors."
The price is $107
$118 total
includes taxes & fees
Jun 16 - Jun 17
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 | Premium bedding, pillowtop beds, desk, blackout drapes
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
2.5 star property
8.4 out of 10, Very Good, (1519)
"Room was nice. Everything - room, property, grounds well kept. Staff friendly and accommodating. So glad we chose to stay there. "
The price is $99
$115 total
includes taxes & fees
May 26 - May 27
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, (571)
"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 $80
$88 total
includes taxes & fees
Jun 16 - Jun 17
Clarion Pointe Richmond North near University
Seasonal outdoor pool
Best Western Winchester Hotel
2.5 star property
8.4 out of 10, Very Good, (819)
"Was really nice place for price. "
The price is $90
$99 total
includes taxes & fees
Jun 3 - Jun 4
Best Western Winchester Hotel
Lobby sitting area
Hotel Lex
2.5 star property
8.0 out of 10, Very Good, (114)
"Good rooms and quality entertainment at the restaurant. Really nice outdoor courtyard "
The price is $102
$119 total
includes taxes & fees
May 27 - May 28
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 $74
$82 total
includes taxes & fees
May 23 - May 24
Red Roof Inn Richmond, KY
Exterior
Super 8 by Wyndham Richmond
2.0 star property
7.6 out of 10, Good, (776)
"The staff was great! My room was clean and accommodating. "
The price is $75
$83 total
includes taxes & fees
May 28 - May 29
Super 8 by Wyndham Richmond
Desk, laptop workspace, iron/ironing board, free cribs/infant beds
Comfort Suites Richmond
2.5 star property
7.6 out of 10, Good, (596)
"The staff was friendly and very accommodating. It was clean and an enjoyable overnight stay."
The price is $98
$108 total
includes taxes & fees
Jun 16 - Jun 17
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 $76
$88 total
includes taxes & fees
May 27 - May 28
Comfort Inn Hamburg Area / I-75 Lexington
Don't see what you're looking for?
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.

More cheap stays in Winchester

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

1938 Stanton Way, Bldg A, Lexington, KY
The price is $71 per night from May 23 to May 24
$71
$83 total
includes taxes & fees
May 23 - May 24
8.4/10 Very Good! (964 reviews)

Stay near popular Winchester attractions

Image for University of Kentucky

University of Kentucky

Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

See properties
University of Kentucky

Winchester Travel Info

Number of reviews
6,115
Accommodation
1,210 hotels
Highest price
$137
Lowest price
$55
Reasons to visit
Bluegrass Heritage Museum, Southwind Golf Course and Lykins Park
Hotels with dining
2
Hotels with free breakfast
6

Frequently asked questions

What's the best place to stay in Winchester?

Hampton Inn Winchester is ranked highly by Expedia customers. This hotel offers free breakfast and free parking. Reviews from our site also recommend Holiday Inn Express Lexington East - Winchester, an IHG Hotel and Best Western Winchester Hotel as top choices for your visit. See all available top hotels, or vacation rentals in Winchester.

What are some of the best vacation rentals in Winchester?

Stay in a 1953 Gunnison Home is within walking distance to St Joe Hospital: This vacation home rental outside Winchester is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. See all vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes, the majority of hotel bookings are fully refundable if cancelled before the hotel’s cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, it might still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

For more information about changing or cancelling your trip to Winchester, head over to our customer service page.

What's the best place to stay on a budget in Winchester?

Based on reviews, Red Roof Inn Lexington - Winchester is a popular hotel for our travelers who want a more economical choice, and features free WiFi and free parking. View all budget hotels in Winchester.

What's the best place to stay for families in Winchester?

Hampton Inn Winchester is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families. Attractions in the area like Lexington Ice Center and Paradise Cove Aquatic Center are also fun for kids of all ages. Find more child-friendly accommodations in Winchester.

What is the favorite LGBTQ-friendly accommodation in Winchester?

Best Western Winchester Hotel is a top LGBTQ-friendly hotel that features free breakfast and free parking. Hampton Inn Winchester and Holiday Inn Express Lexington East - Winchester, an IHG Hotel are two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Winchester.

What's the best pet-friendly place to stay in Winchester?

Baymont by Wyndham Winchester is a top dog-friendly hotel, and offers an indoor pool and a fitness center for its human guests. Other good choices for you and your pet's trip include Best Western Winchester Hotel and Hampton Inn Winchester. See more pet-friendly hotel accommodations in Winchester.

Where is the best hotel to stay close to Community Park?

Best Western Winchester Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and free parking. It's located just a short 0.8 mi (1.3 km) from Community Park. Other good choices within a few miles include Baymont by Wyndham Winchester and Holiday Inn Express Lexington East - Winchester, an IHG Hotel.

What about the best place to stay close to Southwind Golf Course?

One of the top choices for your stay is Best Western Winchester Hotel, located 2.7 mi (4.3 km) from Southwind Golf Course, and this hotel offers free breakfast and free parking. Holiday Inn Express Lexington East - Winchester, an IHG Hotel and Baymont by Wyndham Winchester are two other good choices within 5 miles.

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 accommodations with pools in Winchester?

Baymont by Wyndham Winchester is a top hotel with a pool, free breakfast, and free WiFi. A couple of other options that offer an onsite pool include Best Western Winchester Hotel and Comfort Inn. View all hotels with pools in Winchester.

Recent reviews of Winchester hotels
Expedia verified reviews

Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

5/5 Excellent
"The free snacks were a great addition!"
A verified traveler stayed at Embassy Suites by Hilton Lexington Green
Posted 14 hours ago
Embassy Suites by Hilton Lexington Green