North Middletown Vacation Rentals

Q: What's the top vacation rental that North Middletown has to offer?

Renovated train station on thoroughbred horse farm. : This vacation home rental outside of North Middletown is located in the city center and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

Dates

November 2026

December 2026

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Our top choices for North Middletown vacation rentals

A Farmers' Market pavilion with a clear roof, a sign indicating it's powered by KJ, and operating hours from June through October.

1. Cozy, Bright Home in Historic Downtown

Mount Sterling

Glenda

SAR 434 total

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a bed, nightstands, a ceiling fan, a mural of a sunset, and a window with blinds.

2. 5 o'clock somewhere in Mt Sterling

Mount Sterling

Trey S.

SAR 478 total

includes taxes & fees

8 Nov - 9 Nov

3. Hunting Lodge in the City

Mount Sterling

SAR 497 total

includes taxes & fees

8 Nov - 9 Nov

4. The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling

Mount Sterling

Robert G.

SAR 575 total

includes taxes & fees

30 Nov - 1 Dec

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

5. Charming Victorian Apartment | Downtown Winchester

Winchester

SAR 1,538 total

includes taxes & fees

30 Nov - 1 Dec

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

6. 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

Winchester

Tim T.

SAR 1,047 total

includes taxes & fees

20 Nov - 21 Nov

A rural road curving through a green landscape with a wooden fence, a stone wall, and a small building in the distance.

7. Historical 4-bedroom farmhouse in serene Sharpsburg with AC.

Sharpsburg

Garrett W.

SAR 1,552 total

includes taxes & fees

8 Nov - 9 Nov

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

8. The Winchester

Winchester

Gina

SAR 1,047 total

includes taxes & fees

20 Nov - 21 Nov

A gated entrance with a stone wall, a tree, and white hydrangea flowers.

9. Cabin in Kentucky Horse Country

Bourbon County

Siobann S.

SAR 1,745 total

includes taxes & fees

8 Nov - 9 Nov

A living room with a blue sofa set, a wooden coffee table, and a chandelier.

10. The Parsonage of Paris

Paris

Leslie S.

SAR 1,237 total

includes taxes & fees

14 Nov - 15 Nov

A dining room with a wooden table and chairs, a chandelier, a fireplace, and a mirror on the wall.

11. The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway

Paris

"This property is an older home remodeled. the showers are only for SMALL people. they use horrible smelling air freshners. it took 2 days to get the chemical smell out. And the lights in the bathroom went out after the first day. The price on this home is way to high for the property. But on a good note, the fenced in back yard is huge. the dogs loved it. but the next door neighbor has aggressive pit bulls who go nuts at the fence when they are out. . And after letting the owner know about the...

Randy H.

SAR 1,500 total

includes taxes & fees

9 Nov - 10 Nov

An outdoor patio area with a fire pit, wicker furniture, and a pool.

12. Bluegrass Bourbon Retreat/Pool/ Downtown Paris

Paris

SAR 2,587 total

includes taxes & fees

8 Nov - 9 Nov

A house with a blue door, two windows with shutters, and a porch with a white railing.

13. Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace

Millersburg

SAR 1,219 total

includes taxes & fees

9 Nov - 10 Nov

A doorway leading to a room with a patterned chair and a painting on the wall.

14. Charming Apartment in the Heart of Carlisle

Carlisle

Stephanie D.

SAR 1,021 total

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a beige exterior, numbered 1112, featuring a front porch with two wicker chairs and two wall-mounted lanterns.

15. The Neal House: Charming & Historic 3 Bedroom House

Millersburg

SAR 1,706 total

includes taxes & fees

9 Nov - 10 Nov

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

16. River Relaxation - Calm Riverfront Home in Winchester Kentucky

Winchester

Polly H.

SAR 1,307 total

includes taxes & fees

8 Nov - 9 Nov

A kitchen with a central island, two pendant lights, a stove, and wooden cabinets.

17. Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC

Millersburg

"This property is perfect for families traveling together. Each bedroom has its own bathroom and plenty of room for everyone to relax. The kitchen is perfect and the back porch makes a great place to have your coffee in the morning or in the evening. It’s only 20 minutes from Cynthia Anna and less than 10 minutes from Paris, so if you were looking for a great place to stay look no further! We had an issue with one of the beds and they took care of it within a few hours"

Michelle

SAR 1,880 total

includes taxes & fees

9 Nov - 10 Nov

A two-story house with a front porch, a central door, and a small front yard.

18. The Parsonage: A Grand 19th Century 4 Bedroom Home

Millersburg

SAR 1,839 total

includes taxes & fees

9 Nov - 10 Nov

A house with a covered porch, string lights, and a lawn.

19. Charming Cottage - Near I-75 & Horse Park + Farms

Lexington

Scooby D.

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

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

LEXINGTON

Stephanie S.

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Find vacation rentals that suit your style

Top North Middletown 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 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 Holiday Inn Express & Suites building with a modern design, featuring a covered entrance and stone pillars.

Holiday Inn Express & Suites Mt Sterling North by IHG

Mount Sterling

10/10 Excellent

JimS.

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

A hotel room with a bed, a desk with a chair, a sofa, and a TV.

Comfort Inn & Suites Mount Sterling

Mount Sterling

10/10 Excellent

Gilda

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

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

Baymont by Wyndham Winchester

Winchester

10/10 Excellent

Rick

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

Fairfield Inn & Suites by Marriott Lexington East/I-75

Lexington

10/10 Excellent

Randy

A modern kitchen with grey cabinets, a wooden dining table, and overhead lighting.

Homewood Suites Lexington-Hamburg

Lexington

10/10 Excellent

Charles

A modern bathroom with a blue door, a glass shower enclosure, and a white sink with a mirror.

Spark by Hilton Lexington Hamburg

Lexington

10/10 Excellent

Allison

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

Comfort Inn Winchester

Winchester

10/10 Excellent

Holly H.

A building with a brick facade, surrounded by well-maintained landscaping including various shrubs and flowering plants.

Ramada Limited Mount Sterling

Mount Sterling

10/10 Excellent

Bonnie

Frequently Asked Questions

Can I find a vacation rental in North Middletown?

Yes, we offer vacation rentals near top local attractions in North Middletown, or you can go with a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that North Middletown has to offer?

Renovated train station on thoroughbred horse farm.: This vacation home rental outside of North Middletown is located in the city center and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in North Middletown?

While you're exploring the area, Lake Carnico and College Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find The Cane Ridge Meeting House and Claiborne Farm.

What are vacation rentals like in North Middletown?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in North Middletown. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips or small group gatherings.

North Middletown Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for North Middletown vacation rentals

1. Cozy, Bright Home in Historic Downtown

2. 5 o'clock somewhere in Mt Sterling

3. Hunting Lodge in the City

4. The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling

5. Charming Victorian Apartment | Downtown Winchester

6. 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

7. Historical 4-bedroom farmhouse in serene Sharpsburg with AC.

8. The Winchester

9. Cabin in Kentucky Horse Country

10. The Parsonage of Paris

11. The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway

12. Bluegrass Bourbon Retreat/Pool/ Downtown Paris

13. Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace

14. Charming Apartment in the Heart of Carlisle

15. The Neal House: Charming & Historic 3 Bedroom House

16. River Relaxation - Calm Riverfront Home in Winchester Kentucky

17. Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC

18. The Parsonage: A Grand 19th Century 4 Bedroom Home

19. Charming Cottage - Near I-75 & Horse Park + Farms

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

Find vacation rentals that suit your style

Top North Middletown Hotel Reviews

Holiday Inn Express Lexington East - Winchester by IHG

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in North Middletown?

What's the top vacation rental that North Middletown has to offer?

What can I see and do in North Middletown?

What are vacation rentals like in North Middletown?