Skip to main content

Filter by:


Star Rating

Review Score

Winchester – 6 hotels and places to stay
See the latest prices and deals by choosing your dates.
Best Western Winchester Hotel, hotel in Winchester

This Winchester, Kentucky hotel features an outdoor pool and rooms with free WiFi and cable TV with HBO. Best Western Winchester Hotel is 9 miles from Fort Boonesborough State Park.

The room was clean and nicely decorated. The room has one of the largest TV's I have seen in a room especially at this price (probably a 50"). Breakfast had the most choice at any place we have ever stayed. Hot breakfast included biscuits and gravy, scrambled eggs, sausage patties, bacon pieces and diced potatoes (eggs, bacon pieces and potatoes combined to make a good hash). There were ten different kinds of cereal, various small pastries, etc. In addition to the usual orange juice and apple juice machine, there were several varieties of Healthy Balance juices and there were several gluten free and vegan friendly options.
8.1
Scored 8.1
Very Good
Rated very good
283 reviews
Price from$90.24per night
Hampton Inn Winchester KY, hotel in Winchester

Located just off I-64, this hotel is a 5-minute drive from downtown Winchester. It serves breakfast every morning and features an outdoor pool. An evening reception is offered each night.

Nice location away from the hustle of life.
9.0
Scored 9.0
Wonderful
Rated wonderful
107 reviews
Price from$123.25per night
Holiday Inn Express - Lexington East - Winchester, an IHG Hotel, hotel in Winchester

Located in Winchester and with Fort Boonesborough State Park reachable within 10 miles, Holiday Inn Express - Lexington East - Winchester, an IHG Hotel provides express check-in and check-out,...

Comfortable bed and clean room
8.8
Scored 8.8
Excellent
Rated excellent
172 reviews
Price from$143per night
Baymont by Wyndham Winchester, hotel in Winchester

Baymont by Wyndham Winchester offers rooms with free cable TV and an indoor pool and sauna, easily reached from Interstate 65 in Kentucky’s historic bluegrass country.

Room was Clean , the staff was friendly overall good stay.
6.8
Scored 6.8
Pleasant
Rated pleasant
166 reviews
Price from$79.80per night
Comfort Inn, hotel in Winchester

Located close to Interstate 64, this Winchester hotel offers free WiFi, an indoor pool, and rooms that feature a flat-screen TV and plush bedding. Cassell Creek Golf Course is 3.1 mi away.

The breakfast was decent. The beds were comfortable. The shower was very nice
5.3
Scored 5.3
Average
Rated fair
113 reviews
Price from$75.06per night
Red Roof Inn Lexington - Winchester, hotel in Winchester

Located 3 minutes’ drive from Interstate 64, thisRed Roof Inn Lexington - Winchester hotel is 17 minutes’ drive from the Lexington city center and 25 miles from the Kentucky Horse Park.

Staff was very kind and helpful. The lobby was clean and smelled nice.
6.0
Scored 6.0
Pleasant
Rated pleasant
99 reviews
Price from$65.59per night
Comfort Inn Hamburg Area I-75 Lexington, hotel in Winchester

Comfort Inn Hamburg Area I-75 Lexington in Lexington is conveniently located less than 10 miles from the University of Kentucky and Rupp Arena.

The staff was very helpful and polite.
6.3
Scored 6.3
Pleasant
Rated pleasant
170 reviews
Price from$75.65per night
La Quinta by Wyndham Lexington South / Hamburg, hotel in Winchester

This hotel features an indoor pool, this La Quinta Inn & Suites Lexington South/Hamburg hotel is a 20 mintues' drive from The University of Kentucky and Rupp Arena.

We stay at this hotel at least once a year, usually more. Have done so for many years. Breakfast is good, staff is great.
8.2
Scored 8.2
Very Good
Rated very good
1,152 reviews
Price from$107.07per night
Hotel Lex - Hotel and Conference Center, hotel in Winchester

Located in Lexington, 5.7 miles from The Arboretum, Hotel Lex - Hotel and Conference Center provides accommodations with a fitness center, free private parking, a garden and a shared lounge.

Everything
8.0
Scored 8.0
Very Good
Rated very good
34 reviews
Price from$186per night
Days Inn by Wyndham Lexington Southeast, hotel in Winchester

This Lexington hotel is 9 miles from the University of Kentucky. Days Inn Lexington South serves breakfast to grap and go and features guest rooms with free Wi-Fi and cable TV with HBO.

Nothing. The staff were not friendly whatsoever. They would only give four people one wash rag and if you ask for more they would try to just give you one more and say you already have one. The microwave quit and they tried to wait till the next day to give us another one and when I told them I’m calling Wyndham on them he said I’ll be right there I don’t like your attitude, I said come right on I don’t like how you’re treating us. One of the chairs the seating part was broken and they put a piece of plywood in it and screws and when you sit down my wife got screws in her butt the cut her hand and butt.
6.4
Scored 6.4
Pleasant
Rated pleasant
184 reviews
Price from$53.82per night
See all 6 hotels in Winchester

Most-booked hotels in Winchester in the past month

Subscribe to receive premium deals

Prices drop the second you sign up!

What Guests Said About Winchester:

  • 10
    Scored 10

    My favorite spots at Comfort Inn was in my room in that soft...

    My favorite spots at Comfort Inn was in my room in that soft bed they have. When me and my man ate at Comfort Inn, we sat at the corner table where it is only two chairs and is was in the far corner. Getting around Winchester easy? well I really don't know because I haven't experience walking around Winchester at all yet. Some fun activities for young couples like myself, I would say a nice trip on the beach, or going in the pool for a nice swim, or take many pictures at a beautiful view.
    Crystyle
    United States of America

Explore guest reviews of hotels in Winchester

  • 5.3
    Scored 5.3
    Average
    Rated fair
     · 113 reviews
    The staff was very friendly however I was upset that i specifically chose this hotel for the indoor pool and then found out when I checked in that it had been closed for 3 years due to needing repairs, and there’s also the fact that the toilet wouldn’t flush without being plunged every time
    Ashlie
    United States of America
  • From $178.97 per night
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 107 reviews
    I have for many years used the Hampton brand thinking the premium in price was worth it , twice now I have been left disappointed and out of pocket , I don't know if the whole brand is having issues or I have just been unlucky. The overall hotel is nice .
    john
    United Kingdom
  • From $91.11 per night
    6.8
    Scored 6.8
    Pleasant
    Rated pleasant
     · 166 reviews
    The location right off the highway was very convenient. The owner/staff were very friendly and accommodating. The room was VERY spacious and comfortable. It was more like a suite than just a hotel room.
    Jill
    United States of America
  • From $77.82 per night
    6.0
    Scored 6.0
    Pleasant
    Rated pleasant
     · 99 reviews
    Room was fine but desk chair was extremely stained. Water was hot quickly in the shower. Obviously hotel is undergoing some needed upgrades which is a good thing. Pleasant exterior.
    Bruce
    United States of America
  • 8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 172 reviews
    Most comfortable hotel bed we've ever slept in! Clean, comfortable, convenient to I-64. We travel through here several times per year...this is now our go-to stopover.
    B
    Barbara
    United States of America
  • From $109.95 per night
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 283 reviews
    The Staff were great. Provided us with extra pillows instead if giving the run around like other hotels/motels. Will definitely stay here again.
    James Elder
    United States of America
  • From $178.97 per night
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 107 reviews
    One of the best breakfasts I have ever had at a hotel! The beds were so comfortable to sleep in, instantly was able to fall asleep.
    Jessica
    United States of America
  • From $77.82 per night
    6.0
    Scored 6.0
    Pleasant
    Rated pleasant
     · 99 reviews
    Hotel was clean staff super friendly However you could hear everything outside your room
    Valerie
    United States of America
  • From $109.95 per night
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 283 reviews
    The hotel room was clean as was the the amenities. Breakfast was the best I've ever seen!
    A
    Anonymous
    United States of America
  • 8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 172 reviews
    Breakfast was fine comparable to other hotels.
    D
    Diana
    United States of America
  • From $91.11 per night
    6.8
    Scored 6.8
    Pleasant
    Rated pleasant
     · 166 reviews
    Worst hotel experience I've ever had!!
    David
    United States of America
  • 5.3
    Scored 5.3
    Average
    Rated fair
     · 113 reviews
    Hotel was comfortable!
    Denise
    United States of America