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.

Winchester Vacation Rentals

Q: What are some of the best vacation home rentals that Winchester has to offer?

Luxe Home Downtown - Sleeps 6. Off-street parking : Visitors like this Winchester vacation home rental. It is located in the city center and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. 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. You can relax into your vacation with a garden and a selection of games.

Dates

November 2026

December 2026

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Our top choices for Winchester vacation rentals

A two-story house with a porch and a front yard.

1. Charming Victorian Apartment | Downtown Winchester

Winchester

AED 1,480 total

includes taxes & fees

16 Nov - 17 Nov

A black leather sofa with a center console, a glass table, and two boxes on the table.

2. The Winchester

Winchester

Gina

AED 1,024 total

includes taxes & fees

9 Nov - 10 Nov

A kitchen with white cabinets, a stainless steel oven, and a dishwasher.

3. 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

Winchester

Tim T.

AED 996 total

includes taxes & fees

9 Nov - 10 Nov

A two-story wooden cabin with a balcony, surrounded by trees.

4. River Relaxation - Calm Riverfront Home in Winchester Kentucky

Winchester

Polly H.

AED 1,278 total

includes taxes & fees

8 Nov - 9 Nov

A log cabin interior with a stone fireplace, wooden walls, and a ceiling fan.

5. Natural Bridge State Resort Park

Slade

Logan

AED 227 total

includes taxes & fees

6 Dec - 7 Dec

A log cabin interior with a wooden desk, leather armchair, and a patterned rug.

6. Unique Stay in a 1907 Log Cabin on The Kentucky River

Lexington

Anonymous traveler

AED 678 total

includes taxes & fees

8 Nov - 9 Nov

A log cabin interior with a sofa, a coffee table, a fireplace, and a staircase leading to another room.

7. 1800’s Historical Log Cabin near I-75 Interstate

Lexington

Christopher S.

AED 929 total

includes taxes & fees

8 Nov - 9 Nov

A hotel lobby with a flat-screen TV, a coat rack, a table with chairs, and a view of the outside through large glass doors.

8. 2 Full Beds | Non-Smoking, Micfridge

Lexington

Miguel

AED 235 total

includes taxes & fees

26 Nov - 27 Nov

A wooden deck with two chairs and a small round table, surrounded by lush greenery.

9. Treetops Solar Sanctuary

Chevy Chase

Anna C.

AED 589 total

includes taxes & fees

9 Nov - 10 Nov

A cabin with a deck, a fire pit, and string lights in a forest setting.

10. Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Irvine

Anonymous traveler

AED 684 total

includes taxes & fees

11 Nov - 12 Nov

A modern living room with a glass coffee table, leather armchair, dining area with chairs, and a chandelier.

11. Luxury on Main / South & Downtown Hideaway

Richmond

Jordan B.

AED 636 total

includes taxes & fees

10 Nov - 11 Nov

A kitchen with white cabinets, a central island, and a dining area with wooden chairs and a table.

12. The Towner : Sleeps 4 • Near RRG • Walk to Town

Stanton

lisa s.

AED 787 total

includes taxes & fees

3 Dec - 4 Dec

A campsite with several tents on stilts over a sandy area near a river, surrounded by trees.

13. Furnished Glamping Tent/King Bed/Access to the Red River - Noble Bear - #4

Stanton

Josh N.

AED 462 total

includes taxes & fees

15 Nov - 16 Nov

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

14. Graffiti Art Haus - Walk to Central Bank Arena

Downtown Lexington

Todd S.

AED 853 total

includes taxes & fees

6 Dec - 7 Dec

A hot tub with two people and a bar area with bottles and a lantern.

15. Relaxing Hot Tub | S’mores Fire Pit | Garage

LEXINGTON

Stephanie S.

A brown leather sofa in a living room with a large window, a mirror, and a view of a kitchen.

16. Luxurious 1-bedroom with Free Parking

Lexington

Zoe K.

AED 1,032 total

includes taxes & fees

3 Dec - 4 Dec

A bedroom with a bed, bedside tables, a ceiling fan, a mirror, and a door.

17. Westfield Blue & Gazebo Luxury & Privacy Getaway

Richmond

ZACHARY W.

AED 550 total

includes taxes & fees

17 Nov - 18 Nov

A stone pavilion named Hamburg Pavilion with a flagpole, surrounded by landscaped gardens and trees.

18. Midnight Lexington Newly Remodeled Designer Stay

Lexington

Michael M.

A cabin with a wooden deck, a covered porch, and a small garden area.

19. Larkspur Cabin with Hot Tub near Red River Gorge

Stanton

Anonymous traveler

A wooden deck with a table and chairs, surrounded by a house and greenery.

20. Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington

Downtown Lexington

Maria J.

AED 539 total

includes taxes & fees

15 Nov - 16 Nov

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Find vacation rentals that suit your style

Top Winchester Hotel Reviews

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

Elwood Hotel & Suites

Lexington

10/10 Excellent

Cari

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 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 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 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

A modern living room with a sofa, armchairs, a coffee table, and a dining table. A large window offers a view of the cityscape.

The Manchester

Distillery District

10/10 Excellent

Damon

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 patio with a stone fire pit, seating, and string lights.

Staybridge Suites Lexington - University Area by IHG

Lexington

10/10 Excellent

Hope

A Holiday Inn Express & Suites hotel with a modern design, multiple floors, and a parking lot with various vehicles.

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

Lexington

10/10 Excellent

catherine

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 reception area with a black counter, a small seating area, and a view of the outside.

Asbury Inn & Suites

Wilmore

10/10 Excellent

James

Frequently Asked Questions

Are there vacation rentals in Winchester?

Yes, we offer vacation rentals close to top points of interest in Winchester, or you can choose a more secluded option if you want a relaxing place to stay. Our travelers say Winchester has a good selection of restaurants. Make sure you have time to check out the coffeehouses and shopping during your trip.

What are some of the best vacation home rentals that Winchester has to offer?

Luxe Home Downtown - Sleeps 6. Off-street parking: Visitors like this Winchester vacation home rental. It is located in the city center and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. 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. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Winchester?

Expedia has 9 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

College Park and GRCHS Baseball Field are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Cassell Creek Golf Course and Winchester Opera House are other places to visit while you're in town.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Winchester. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.

Winchester Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester vacation rentals

1. Charming Victorian Apartment | Downtown Winchester

2. The Winchester

3. 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4. River Relaxation - Calm Riverfront Home in Winchester Kentucky

5. Natural Bridge State Resort Park

6. Unique Stay in a 1907 Log Cabin on The Kentucky River

7. 1800’s Historical Log Cabin near I-75 Interstate

8. 2 Full Beds | Non-Smoking, Micfridge

9. Treetops Solar Sanctuary

10. Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

11. Luxury on Main / South & Downtown Hideaway

12. The Towner : Sleeps 4 • Near RRG • Walk to Town

13. Furnished Glamping Tent/King Bed/Access to the Red River - Noble Bear - #4

14. Graffiti Art Haus - Walk to Central Bank Arena

15. Relaxing Hot Tub | S’mores Fire Pit | Garage

16. Luxurious 1-bedroom with Free Parking

17. Westfield Blue & Gazebo Luxury & Privacy Getaway

18. Midnight Lexington Newly Remodeled Designer Stay

19. Larkspur Cabin with Hot Tub near Red River Gorge

20. Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

Holiday Inn Express Lexington East - Winchester by IHG

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Winchester?

What are some of the best vacation home rentals that Winchester has to offer?

How many vacation rentals are there in Winchester?

What can I see and do in Winchester?

What are vacation rentals like in Winchester?