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.

Search and Rent Winchester Condos

Where to?

Dates

November 2026

December 2026

Bundle & Save
Get more, spend less whenever you see Bundle & Save deals
OneKeyCash
Earn OneKeyCash on all your eligible bookings
Upfront pricing
We are not like the others - we include taxes and fees

Find vacation rentals that suit your style

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Winchester condo rentals

A covered porch with a wooden door, white railings, and a view of a grassy yard and parked cars.

1. Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington

Lexington

V K.

$247 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern living room with a sofa, armchairs, and a coffee table. There is a kitchen area with a bar and pendant lights.

2. Graffiti Art Haus - Walk to Central Bank Arena

Downtown Lexington

Todd S.

$180 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern apartment with a living room, kitchen, and dining area.

3. This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

Lexington

Andrew K.

$160 nightly

Nov 16 - Nov 17

Total with taxes and fees

A wooden deck leading to a red door, brick walls, and a white door in the background.

4. War Admiral @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown/GT College

Georgetown

Kiri B.

$222 nightly

Nov 22 - Nov 23

Total with taxes and fees

A modern kitchen with a central island, stainless steel appliances, and a dining area with wooden chairs and a table.

5. HUGE 3BR Penthouse King bed. Walk 2 RUPP elevator

Downtown Lexington

Heather C.

$452 nightly

Nov 7 - Nov 8

Total with taxes and fees

6. Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College

Georgetown

Rebecca M.

$271 nightly

Nov 16 - Nov 17

Total with taxes and fees

7. Secretariat @ The HoM- Ky Horse Park 11min, Ark 30min, Walk Downtown/GT College

Georgetown

Danielle B.

$271 nightly

Nov 16 - Nov 17

Total with taxes and fees

8. Sir Barton @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown / GT College

Georgetown

Nicole B.

$222 nightly

Nov 22 - Nov 23

Total with taxes and fees

View all properties

Learn more about Winchester

Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.

See all hotels in Winchester

Top reviews in Winchester

A Holiday Inn Express building with a covered entrance, stone pillars, and potted plants.

Holiday Inn Express Lexington East - Winchester by IHG

Winchester

10/10 Excellent

Dennis

A hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.

Hampton Inn Winchester

Winchester

10/10 Excellent

JDK

A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.

Best Western Winchester Hotel

Winchester

10/10 Excellent

Kimbery

A hotel room with a bed, a desk, a chair, a desk lamp, a window with curtains, an air conditioner, and a view of the outside.

Value Stay

Winchester

10/10 Excellent

This is a money saver motel. No frills, no bugs and no extras. The refrigerator, microwave and air conditioner and toilet were near new and functioning well. The carpet and sink are original from 1989 and in poor shape, the sink was draining very slowly but for the price of a clean room without bugs it wasn't an issue for us. The water saver shower head was annoying as could be but it's a hot shower and it was definitely clean so we lived with it. This isn't a vacation resort but if you're...

Crystal

A swimming pool with wooden walls and large windows offering views of greenery.

Baymont by Wyndham Winchester

Winchester

10/10 Excellent

Rick

An indoor swimming pool with tiled flooring, orange walls, and potted plants.

Comfort Inn Winchester

Winchester

10/10 Excellent

Holly H.

A modern cafe with wooden furniture, a self-service beverage station, and a flat-screen TV on the wall.

Home2 Suites Lexington Keeneland Airport, KY

Beaumont Residential

10/10 Excellent

Monte

An outdoor patio area with tables and chairs, a wooden pergola, and a brick wall.

Home2 Suites By Hilton Richmond, Ky

Richmond

10/10 Excellent

Melinda

An indoor swimming pool with a wooden ceiling, tiled walls, and a seating area with chairs and a table.

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Lexington

10/10 Excellent

karen

An outdoor seating area with modern furniture, planters, and a building in the background.

Elwood Hotel & Suites

Lexington

10/10 Excellent

Cari

A modern kitchen with a long counter, bar stools, and hanging light fixtures.

Residence Inn by Marriott Lexington South/Hamburg Place

Liberty Area

10/10 Excellent

We had stayed in Residence Inns before, but this one had rooms arranged a little differently. At least ours was...kind of all one room arrangement. However it was very comfortable and functional. The room was nicely furnished and clean, as was the rest of the hotel. Breakfast was amazing for a free breakfast. I had to force myself not to be a piglet. The nearby neighborhood has a super selection of great restaurants and stores, very convenient. You could honestly walk there if you were so...

Suzann

A modern hotel with a prominent red and grey facade, multiple windows, and a well-lit entrance.

avid hotel Lexington - Hamburg Area by IHG

Lexington

10/10 Excellent

Very pleasantly surprised by the room minimal foot print. The design of the room was excellent. Modern yet retro look. W Paul’s Recommend getting a top floor room as the soundproofing is a bit off the mark. We traveled with our dog and there was a minor discrepancy in the pet fee at registration versus what the web site information available. Overall very pleased and we will certainly stay again at Avid.

Kimberly

An outdoor seating area with a fire feature, yellow chairs, and a colorful sofa.

Home2 Suites by Hilton Lexington Hamburg

Lexington

10/10 Excellent

Debora

A large indoor swimming pool with a tiled floor, surrounded by large windows and a seating area with tables and chairs.

Holiday Inn Express Lexington - Horse Park Area by IHG

Lexington

10/10 Excellent

Trina

An outdoor seating area with wicker furniture and a fire pit, adjacent to a building with large windows and a brick facade.

TownePlace Suites by Marriott Lexington Keeneland/Airport

Beaumont Residential

10/10 Excellent

Cathy

A buffet area with multiple self-service stations for different food items.

Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG

Lexington

10/10 Excellent

catherine

A cozy lounge area with a blue sofa, round coffee tables, and a wooden archway.

The Manchester

Distillery District

10/10 Excellent

KIRSTEN

Frequently Asked Questions

Why book your condo in Winchester with Expedia?

Getting away shouldn't be difficult, so if you're on the lookout for condos at an affordable rate, Expedia has got your back. Keep costs down and select something small and affordable, or splurge on a luxury condo and spoil your favorite people. Our search filters make it a breeze to find a property in Winchester that matches your needs.

How can I find cheap condos in Winchester?

A great way to score cheap condos in Winchester is with Expedia's useful filter tool. Narrow down your search results by budget, amenities and star rating to snag unbeatable prices in just a few clicks.

What is there to do in Winchester near my condo?

Once you've settled into your hotel, venture out and discover the fantastic things Winchester has on offer. Southwind Golf Course is a top attraction to add to your travel itinerary.

Explore a world of travel with Expedia

Winchester Vacation Rentals
Standard Link for Winchester Vacation Rentals

Search and Rent Winchester Condos

Bundle & Save

OneKeyCash

Upfront pricing

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Winchester condo rentals

1. Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington

2. Graffiti Art Haus - Walk to Central Bank Arena

3. This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

4. War Admiral @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown/GT College

5. HUGE 3BR Penthouse King bed. Walk 2 RUPP elevator

6. Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College

7. Secretariat @ The HoM- Ky Horse Park 11min, Ark 30min, Walk Downtown/GT College

8. Sir Barton @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown / GT College

Learn more about Winchester

Top reviews in Winchester

Holiday Inn Express Lexington East - Winchester by IHG

10/10 Excellent

Frequently Asked Questions

Why book your condo in Winchester with Expedia?

How can I find cheap condos in Winchester?

What is there to do in Winchester near my condo?

Explore a world of travel with Expedia