A river winding through a densely forested valley with rocky cliffs on one side.

Montgomery County Vacation Rentals

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Our top choices for Montgomery County 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

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very good, (25 reviews)
"This is definitely an older home, but it was clean and comfortable and the Dolly memorabilia is amazing!"
United States
Glenda
The price is CA $89
CA $176 total
includes taxes & fees
Oct 19 - Oct 20
Cozy, Bright Home in Historic Downtown
A building with a staircase leading to a door marked with the number 218.

2. 1 Bedroom Bourbon House on the Hill

1 Bedroom Bourbon House on the Hill
Mount Sterling
10.0 out of 10, Exceptional, (2 reviews)
"This property was very welcoming to our small dog."
United States
Anne D.
The price is CA $140
CA $186 total
includes taxes & fees
Oct 25 - Oct 26
1 Bedroom Bourbon House on the Hill
A bedroom with a bed, nightstands, a ceiling fan, a mural of a sunset, and a window with blinds.

3. 5 o'clock somewhere in Mt Sterling

5 o'clock somewhere in Mt Sterling
Mount Sterling
9.4 out of 10, Exceptional, (3 reviews)
"A good stay in a friendly area."
United States
Trey S.
The price is CA $146
CA $193 total
includes taxes & fees
Oct 19 - Oct 20
5 o'clock somewhere in Mt Sterling
A bedroom with a bed, a ceiling fan, a TV, and large windows.

4. New, Cozy, Secluded Cabin

New, Cozy, Secluded Cabin
Jeffersonville
8.0 out of 10, Very good, (8 reviews)
"Great host, beautiful property, exactly as listed, steep driveway entrance but awesome overall!"
United States
Edgar O.
The price is CA $148
CA $276 total
includes taxes & fees
Oct 28 - Oct 29
New, Cozy, Secluded Cabin
Exterior

5. Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
The price is CA $153
CA $200 total
includes taxes & fees
Oct 19 - Oct 20
Hunting Lodge in the City
A kitchen with white cabinets, a central island, and a dining area with wooden chairs and a table.

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

The Towner : Sleeps 4 • Near RRG • Walk to Town
Stanton
9.8 out of 10, Exceptional, (52 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
The price is CA $127
CA $303 total
includes taxes & fees
Oct 26 - Oct 27
The Towner : Sleeps 4 • Near RRG • Walk to Town
A log cabin interior with a stone fireplace, wooden walls, and a ceiling fan.

7. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,103 reviews)
"Close to multiple trails and restaurants."
United States
Curtis
The price is CA $109
CA $120 total
includes taxes & fees
Nov 8 - Nov 9
Natural Bridge State Resort Park
A campsite with several tents on stilts over a sandy area near a river, surrounded by trees.

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

Furnished Glamping Tent/King Bed/Access to the Red River - Noble Bear - #4
Stanton
9.8 out of 10, Exceptional, (53 reviews)
"Great stay"
United States
Josh N.
The price is CA $92
CA $195 total
includes taxes & fees
Oct 21 - Oct 22
Furnished Glamping Tent/King Bed/Access to the Red River - Noble Bear - #4
A small wooden cabin with a porch, an American flag, and a small garden.

9. The Cozy Den

The Cozy Den
Wellington
9.8 out of 10, Exceptional, (98 reviews)
"Great place to stay for a small group!"
United States
Adalyn B.
The price is CA $120
CA $247 total
includes taxes & fees
Oct 19 - Oct 20
The Cozy Den
A log cabin interior with a dining area, a sofa, a fireplace, and a television.

10. • KNOTTY PINE•Cozy Cabin in RRG • Hot Tub • Fireplace • Pond for Fishing

• KNOTTY PINE•Cozy Cabin in RRG • Hot Tub • Fireplace • Pond for Fishing
Pine Ridge
9.8 out of 10, Exceptional, (49 reviews)
"Loved the location. And would definitely stay again."
United States
William
The price is CA $184
CA $318 total
includes taxes & fees
Nov 8 - Nov 9
• KNOTTY PINE•Cozy Cabin in RRG • Hot Tub • Fireplace • Pond for Fishing
A red building with a covered porch, two potted plants, a grill, and a ladder.

11. Beautiful Country Sunsets I

Beautiful Country Sunsets I
Hillsboro
9.6 out of 10, Exceptional, (69 reviews)
"Very nice, serene, and personable and the owners were excellent. Great sunrise and sunsets and the stars at night were amazing. "
United States
Simple
The price is CA $120
CA $204 total
includes taxes & fees
Oct 19 - Oct 20
Beautiful Country Sunsets I
A cabin with a deck, a fire pit, and string lights in a forest setting.

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

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (132 reviews)
"Super cute cabin! We enjoyed every minutes and will be back!"
United States
Heather A.
The price is CA $135
CA $286 total
includes taxes & fees
Oct 29 - Oct 30
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Interior

13. Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods

Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods
Stanton
10.0 out of 10, Exceptional, (341 reviews)
"I absolutely loved everything about this cabin! Can’t wait to book again! Very clean and relaxing!"
United States
Jacinda P.
The price is CA $214
CA $394 total
includes taxes & fees
Oct 22 - Oct 23
Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods
A cozy cabin-style kitchen with wooden walls, a loft area, and basic amenities including a refrigerator, stove, and microwave.

14. The Stillhouse Cabin, mins from Red River Gorge

The Stillhouse Cabin, mins from Red River Gorge
Campton
9.6 out of 10, Exceptional, (129 reviews)
"It was a beautiful little cabin. Could use some deep cleaning but overall had all needed necessities. Driveway is exactly as you see it, off the beaten path. Had a great experience!"
United States
Jonathan
The price is CA $141
CA $242 total
includes taxes & fees
Oct 22 - Oct 23
The Stillhouse Cabin, mins from Red River Gorge
A log cabin interior with a blue sofa, wooden cabinets, a kitchen area, and a television.

15. Cozy Cabin Near Cave Run Lake & Marina #1

Cozy Cabin Near Cave Run Lake & Marina #1
Morehead
9.8 out of 10, Exceptional, (67 reviews)
"Perfect location to stay to enjoy all the things Cave Run Lake has to offer! Cabin is clean and perfect for an intimate weekend getaway! We really enjoyed our stay!"
United States
Hannah M.
The price is CA $140
CA $263 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Cabin Near Cave Run Lake & Marina #1
A log cabin with a black door, a porch with chairs, and a small deck area.

16. Cave Run Lodge - Near Lake - Playground & Fire pit - Cabin #6

Cave Run Lodge - Near Lake - Playground & Fire pit - Cabin #6
Morehead
9.6 out of 10, Exceptional, (14 reviews)
"Me and my sister stayed there so that we could visit with family. It was big enough for everything that we needed very enjoyable stay."
United States
henry h.
The price is CA $122
CA $243 total
includes taxes & fees
Oct 26 - Oct 27
Cave Run Lodge - Near Lake - Playground & Fire pit - Cabin #6
A small, single-story cabin with a porch, surrounded by trees.

17. Quiet relaxing Cabin in Wellington backed up to Daniel Boone National Forest.

Quiet relaxing Cabin in Wellington backed up to Daniel Boone National Forest.
Wellington
10.0 out of 10, Exceptional, (18 reviews)
"Great stay!"
United States
Lisa W.
The price is CA $112
CA $316 total
includes taxes & fees
Nov 1 - Nov 2
Quiet relaxing Cabin in Wellington backed up to Daniel Boone National Forest.
A dining table with two plates of food, two beer bottles, and a vase with flowers.

18. Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape

Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape
Stanton
10.0 out of 10, Exceptional, (43 reviews)
"Love the area and the stay was great! Thanks for the communication we had a great time. "
United States
Holly,
The price is CA $200
CA $358 total
includes taxes & fees
Oct 21 - Oct 22
Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape
A wooden cabin interior with a kitchen featuring a stove, microwave, and refrigerator.

19. Plum Crazy: Frenchburg Cabin on 1 Acre

Plum Crazy: Frenchburg Cabin on 1 Acre
Frenchburg
9.6 out of 10, Exceptional, (16 reviews)
"This is the perfect little cabin for a getaway! It was clean, had all the amenities we needed, and the hot tub was a huge plus."
United States
Robert
The price is CA $156
CA $435 total
includes taxes & fees
Oct 25 - Oct 26
Plum Crazy: Frenchburg Cabin on 1 Acre
A spa area with a hot tub and a view of a kitchen through a window.

20. Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge

Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge
Stanton
10.0 out of 10, Exceptional, (139 reviews)
"Great location, and super unique!"
United States
JR C.
The price is CA $214
CA $385 total
includes taxes & fees
Oct 19 - Oct 20
Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Montgomery County Hotel Reviews

Wolf Pup- A Frame- Hillside Tiny Cottage Wi-Fi

Wolf Pup- A Frame- Hillside Tiny Cottage Wi-Fi

10/10 Excellent
"Fabulous weekend exploring the gorge with my daughter. And this cabin was so unique and just added to the fun experience! The property is well-maintained with modern decor. Bed was comfortable. Appreciated the extra touches of a space heater, games and record player. Spectacular view off the back porch. Keep in mind it is essentially “glamping” and definitely feels rustic but we knew that going into it. We were glad we chose to pack in most of our food as the restaurant/grocery store options are very slim. Would recommend to anyone wanting a unique tiny home experience in nature!"
jen r. 3-night trip
Posted 8 hours ago
Wolf Pup- A Frame- Hillside Tiny Cottage Wi-Fi

Find out more about Montgomery County

Everything you need to know about Montgomery County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montgomery County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Montgomery County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montgomery County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montgomery County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montgomery County vacation rentals we have selected for you start as low as CA $120 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Montgomery County rentals

At Expedia, we put the best Montgomery County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Montgomery County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montgomery County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montgomery County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.