An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

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Check availability on Winchester Cheap Hotels

Tonight
Oct 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Winchester cheap hotels

An indoor swimming pool with a wooden ceiling, tiled walls, and a seating area with chairs and a table.
A modern hotel room with a bed, a desk, a chair, a sofa, and a large mirror.
A lobby with a sofa, armchairs, a fireplace, a TV, and a patterned rug.
A multi-story hotel with a prominent 'LaQuinta' sign, a covered entrance, and a parking lot.

1. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Lexington
United States
Sheila
￥13,792
￥16,008 total
includes taxes & fees
Nov 8 - Nov 9
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
A hotel lobby with blue walls, a seating area with blue chairs, a bar, and artwork on the walls.
A hotel room with two beds, a bathroom, and a hallway.
A spacious lobby with a high ceiling, large windows, and a blue accent wall. There are multiple seating areas with chairs and tables, and a television mounted on the wall.
An indoor swimming pool with a lifeguard station, poolside chairs, and a clear 3 FT depth marking.

2. GuestHouse Lexington

GuestHouse Lexington
Lexington
United States
Charles
￥10,628
￥12,336 total
includes taxes & fees
Oct 28 - Oct 29
GuestHouse Lexington
A large indoor swimming pool with a tiled floor, surrounded by large windows and a seating area with tables and chairs.
A multi-story hotel with a curved entrance canopy, large windows, and a modern design.
A modern dining area with a central white table surrounded by blue chairs, a flat-screen TV mounted on the wall, and large windows offering a view of the outside.
A modern hotel lobby with a long communal table, blue and orange seating, a coffee station, and a large wooden door.

3. Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG
Lexington
United States
Sherri
￥14,552
￥16,890 total
includes taxes & fees
Nov 3 - Nov 4
Holiday Inn Express Lexington - Horse Park Area by IHG
A modern reception area with a wooden ceiling, a reception desk, seating arrangements, and a mural of horses.
A hotel room with two beds, a desk, a chair, and a TV.
A hotel with a covered entrance, a bell tower, and a parking lot.
A vending machine stocked with various beverages and snacks, including sodas and chips.

4. Clarion Pointe Richmond North near University

Clarion Pointe Richmond North near University
Richmond
United States
Tracy
￥11,099
￥12,236 total
includes taxes & fees
Nov 22 - Nov 23
Clarion Pointe Richmond North near University
A spacious lobby with a large seating area, a coffee bar, and a view of the kitchen area.
A hotel room with a bed, a desk, a television, a chair, a sofa, and a window with curtains.
A banquet hall with round tables set for a formal event, featuring floral centerpieces and candles.
A buffet setup with clear glass serving stations and a coffee machine in the background.

5. Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park
Lexington
United States
Melody
￥8,394
￥9,743 total
includes taxes & fees
Nov 22 - Nov 23
Quality Inn Lexington -Horse Park
A hotel room with a bed, a desk, a chair, a television, and a bathroom.
A hotel room with a desk, chair, coat rack, wall-mounted TV, and a red chair.
A hotel reception area with a wooden reception desk, a red wall with a 'Free Wi-Fi All Rooms' sign, a stone wall with a 'Red Roof Inn' sign, and a black and red doormat.
A Red Roof Inn with a covered entrance, multiple windows, and a parking lot.

6. Red Roof Inn Richmond, KY

Red Roof Inn Richmond, KY
Richmond
United States
Leeann
￥8,469
￥9,336 total
includes taxes & fees
Nov 4 - Nov 5
Red Roof Inn Richmond, KY
A reception area with a stone wall, a Baymont Inn & Suites sign, a refrigerator stocked with beverages, and a wooden counter.
A hotel room with a bed, a sofa, a small table, and a bathroom.
A Baymont Inn & Suites building with a prominent sign, a covered entrance, and a parking lot.
A restaurant with wooden tables and chairs, a counter with a coffee machine, and a television mounted on the wall.

7. Baymont by Wyndham Georgetown/Lexington North

Baymont by Wyndham Georgetown/Lexington North
Georgetown
United States
Mari
￥11,024
￥12,153 total
includes taxes & fees
Nov 4 - Nov 5
Baymont by Wyndham Georgetown/Lexington North
You will love this destination.
An outdoor patio area with wicker furniture, a stone fire pit, and a view of a multi-story building with large windows.
A hotel lobby with a granite bar, seating area, and a stone accent wall.
An indoor swimming pool with clear water, tiled walls, and a 'NO DIVING' sign.

8. 1 Bedroom | Indoor Pool. Free Daily Breakfast

1 Bedroom | Indoor Pool. Free Daily Breakfast
Lexington
￥31,977
￥42,442 total
includes taxes & fees
Nov 8 - Nov 9
1 Bedroom | Indoor Pool. Free Daily Breakfast
A bedroom with a bed, a window with blinds, a bedside table, a lamp, and a door leading to another room.
A living room with a red sofa, a TV, a small table, and a decorative rug.
A living room with a red sofa, a black table, a flat-screen TV, a fireplace, and a door leading outside.
A hallway with a window, a wooden table with stools, and a red striped rug.

9. Hallelujah Acres Side 2

Hallelujah Acres Side 2
Georgetown
United States
Amelia D.
￥16,240
￥38,144 total
includes taxes & fees
Nov 4 - Nov 5
Hallelujah Acres Side 2
A hot tub with a view of a forest, a ceiling fan, and a painting on the wall.
A bedroom with a wooden bed frame, a large window, and a painting on the wall.
A modern two-story house with a covered porch and a small tower-like structure on the roof.
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen in the background.

10. New Barndominium/12 Guest /2 Hot Tubs/ 2 Kitchens/ 2 Firepits

New Barndominium/12 Guest /2 Hot Tubs/ 2 Kitchens/ 2 Firepits
Stanton
United States
Anonymous traveler
￥54,189
￥118,190 total
includes taxes & fees
Nov 17 - Nov 18
New Barndominium/12 Guest /2 Hot Tubs/ 2 Kitchens/ 2 Firepits
View all properties

Top Winchester Hotel Reviews

Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"Great"
Hana 2-night trip
Posted 10 hours ago
Natural Bridge State Resort Park
Motel 6 Lexington I-75 Hamburg

Motel 6 Lexington I-75 Hamburg

10/10 Excellent
"My stay was great room was clean and well stocked with toiletries, good place to stay needed some attention"
Michael 1-night trip
Posted 1 day ago
Motel 6 Lexington I-75 Hamburg
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"We had a great stay! Everything was very clean. The breakfast was amazing with made to order omelettes & waffles & very spacious dining room. It would have been nice to have queens beds instead of double size, but for one night, it was fine. Overall a positive experience!"
Kimberly 1-night trip
Posted 3 days ago
Embassy Suites by Hilton Lexington Green

Frequently asked questions

What is Winchester like for travelers on a budget?
Explore cheap places to stay in Winchester on Expedia.com and plan a vacation that stays within your budget. Winchester is a destination that visitors enjoy for its dining options. You can look through a wide range of accommodation choices with Member Prices to find the best deal for you. With our site's handy page filters, you can search by price per night, or by favorite amenities like free parking and free WiFi. Or, try refining your search with the location filters to see affordable options around local attractions, such as Bluegrass Heritage Museum or Cassell Creek Golf Course. As you browse, use the heart button to keep track of your favorites so that you can return to them easily when you're ready to decide. Interested in a flight or a rental car too? Take a look at the Bundle and Save vacation packages and discover big savings when you book your transportation at the same time.
When is the best time for a budget trip to Winchester?
Weather will likely play an important role when you plan your trip to Winchester, and keep in mind that cheaper options are usually available when the weather isn't as good. 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.
What is there to see and do in Winchester?
Winchester is known for its dining options and offers things to see and do without spending a fortune. You can budget for the local attractions that interest you most, and then plan some activities that cost little or nothing at all. If you're eager to get outdoors, you can enjoy the natural setting at College Park, GRCHS Baseball Field, or Community Park.
How can I get to Winchester and get around on a budget?
Scoping out the transportation options in Winchester is a smart way to keep your trip affordable. The closest airport is Blue Grass Airport (LEX), 23 mi (37.1 km) away. Winchester might not have many public transit options so renting a car could be an economical alternative to explore more of the area.

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