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Find hotels in Winchester, KY from CA $76

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May 13 - May 14
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May 14 - May 15
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Top 10 Winchester hotels and places to stay

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 CA $180
CA $244 total
includes taxes & fees
May 21 - May 22
Sunset Ridge ~ Rustic & Tranquil 100-Acre Getaway!
Living area
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 CA $123
CA $241 total
includes taxes & fees
May 16 - May 17
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 CA $138
CA $280 total
includes taxes & fees
May 20 - May 21
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 CA $196
CA $217 total
includes taxes & fees
May 28 - May 29
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 CA $279
CA $307 total
includes taxes & fees
May 29 - May 30
TownePlace Suites by Marriott 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, (336)
"Property is located behind a strip mall with no signage and how to get to it"
The price is CA $138
CA $154 total
includes taxes & fees
Jun 9 - Jun 10
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, (754)
"Very clean and comfortable. Friendly staff"
The price is CA $174
CA $191 total
includes taxes & fees
May 26 - May 27
Holiday Inn Express & Suites Richmond, an IHG Hotel
Premium bedding, in-room safe, iron/ironing board
Hampton Inn Richmond
2.5 star property
9.0 out of 10, Wonderful, (1003)
"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 CA $138
CA $152 total
includes taxes & fees
May 27 - May 28
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 CA $150
CA $165 total
includes taxes & fees
May 19 - May 20
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, (1527)
"The property is located in an easy to get to area. Check-in was easy and staff was friendly. "
The price is CA $112
CA $130 total
includes taxes & fees
May 16 - May 17
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 CA $107
CA $118 total
includes taxes & fees
May 26 - May 27
Clarion Pointe Richmond North near University
Seasonal outdoor pool
Best Western Winchester Hotel
2.5 star property
8.4 out of 10, Very good, (817)
"Very friendly staff, great breakfast."
The price is CA $123
CA $136 total
includes taxes & fees
May 19 - May 20
Best Western Winchester Hotel
Lobby sitting area
Hotel Lex
2.5 star property
8.0 out of 10, Very good, (110)
"It was nice and clean. Not bathtub in our room. That upset me. "
The price is CA $153
CA $178 total
includes taxes & fees
May 15 - May 16
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 CA $99
CA $109 total
includes taxes & fees
May 20 - May 21
Red Roof Inn Richmond, KY
Exterior
Super 8 by Wyndham Richmond
2.0 star property
7.6 out of 10, Good, (773)
"The staff was great! My room was clean and accommodating. "
The price is CA $103
CA $113 total
includes taxes & fees
May 21 - May 22
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, (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 CA $149
CA $165 total
includes taxes & fees
May 15 - May 16
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 CA $103
CA $120 total
includes taxes & fees
May 16 - May 17
Comfort Inn Hamburg Area / I-75 Lexington
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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

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.

What is the best spa hotel in Winchester?

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

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

Franklin Ridge Farms Winchester Between Lexington 20 min. & Stanton 15min. is a favorite water park hotel in WinchesterCheck out all hotels with or near waterparks in Winchester.

What is the best accommodation for staying close to Blue Grass Airport (LEX)?

Chateau Annette is a popular 3.5-star B&B featuring free breakfast and free parking. It's located a short 1.8 mi (3 km) from Blue Grass Airport. Other good choices close to the airport include Comfort Suites and Americas Best Value Inn Blue Grass Airport.

How is it to stay in Winchester?

Visitors to Winchester are sure to enjoy the restaurants. Tourists can also enjoy the city's coffeehouses, shopping, and football games. In Winchester, there are 18 hotels and other accommodations to choose from. Find out more about Winchester.

What is there to see in 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 agenda are Bluegrass Heritage Museum and Southwind Golf Course. Check out what more to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches.