Montgomery County Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Top cities in Montgomery County

An aerial view of a town with historic buildings, a central green area, and a parking lot.
Vacation Rentals

Mount Sterling

Mount Sterling

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Montgomery County holiday 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 NZ$205
includes taxes & fees
11 Nov - 12 Nov
Cozy, Bright Home in Historic Downtown
A bedroom with a bed, a ceiling fan, a TV, and large windows.

2. New, Cozy, Secluded Cabin

New, Cozy, Secluded Cabin
Jeffersonville
8.4 out of 10, Very good, (9 reviews)
"Great host, beautiful property, exactly as listed, steep driveway entrance but awesome overall!"
United States
Edgar O.
The price is NZ$327
includes taxes & fees
11 Nov - 12 Nov
New, Cozy, Secluded Cabin
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
9.0 out of 10, Wonderful, (4 reviews)
"A good stay in a friendly area."
United States
Trey S.
The price is NZ$226
includes taxes & fees
11 Nov - 12 Nov
5 o'clock somewhere in Mt Sterling
Exterior

4. Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
The price is NZ$235
includes taxes & fees
11 Nov - 12 Nov
Hunting Lodge in the City
Private kitchen

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

The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
Mount Sterling
10.0 out of 10, Exceptional, (3 reviews)
"Very easy check in and nice location"
United States
Robert G.
The price is NZ$272
includes taxes & fees
30 Nov - 1 Dec
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
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 NZ$374
includes taxes & fees
11 Nov - 12 Nov
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, (2,139 reviews)
"Love staying here, such easy access to the Gorge and Natural Bridge. Always convenient and easy to deal with. Always a place I keep in mind when I’m staying in the area."
United States
Logan
The price is NZ$110
includes taxes & fees
7 Dec - 8 Dec
Natural Bridge State Resort Park
A log cabin interior with a blue sofa, wooden cabinets, a kitchen area, and a television.

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

Cozy Cabin Near Cave Run Lake & Marina #1
Morehead
9.8 out of 10, Exceptional, (68 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 NZ$303
includes taxes & fees
18 Nov - 19 Nov
Cozy Cabin Near Cave Run Lake & Marina #1
A campsite with several tents on stilts over a sandy area near a river, surrounded by trees.

9. 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, (60 reviews)
"Great stay"
United States
Josh N.
The price is NZ$223
includes taxes & fees
11 Nov - 12 Nov
Furnished Glamping Tent/King Bed/Access to the Red River - Noble Bear - #4
A kitchen with wooden walls, a central island, black cabinets, and a white countertop.

10. Boone's Bluff RRG- HUMBLE COZY STAY w/ Firepit

Boone's Bluff RRG- HUMBLE COZY STAY w/ Firepit
Pine Ridge
9.8 out of 10, Exceptional, (48 reviews)
"Super clean and beautiful property. Really good getaway for couples to explore the area! Trails are super close to this property"
United States
Ty A.
The price is NZ$360
includes taxes & fees
12 Nov - 13 Nov
Boone's Bluff RRG- HUMBLE COZY STAY w/ Firepit
A cabin with a deck, a fire pit, and string lights in a forest setting.

11. 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, (134 reviews)
"It was a great cozy place for a weekend for me and my sister. It had everything we needed and we especially loved having the window bed! Would definitely consider staying here again."
United States
Anonymous traveller
The price is NZ$334
includes taxes & fees
11 Nov - 12 Nov
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
A small wooden cabin with a porch, an American flag, and a small garden.

12. The Cozy Den

The Cozy Den
Wellington
9.8 out of 10, Exceptional, (100 reviews)
"Great place to stay for a small group!"
United States
Adalyn B.
The price is NZ$295
includes taxes & fees
11 Nov - 12 Nov
The Cozy Den
A red building with a covered porch, two potted plants, a grill, and a ladder.

13. 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 NZ$241
includes taxes & fees
2 Dec - 3 Dec
Beautiful Country Sunsets I
A cabin with a fire pit, seating, and a porch.

14. Dog-friendly cabin near Nada Tunnel with hot tub

Dog-friendly cabin near Nada Tunnel with hot tub
Slade
10.0 out of 10, Exceptional, (7 reviews)
"Cozy bungalow, very clean, great location and very relaxing. We loved staying there. Hope to revisit soon."
United States
Timothy
The price is NZ$467
includes taxes & fees
30 Nov - 1 Dec
Dog-friendly cabin near Nada Tunnel with hot tub
A cozy cabin-style kitchen with wooden walls, a loft area, and basic amenities including a refrigerator, stove, and microwave.

15. The Stillhouse Cabin, mins from Red River Gorge

The Stillhouse Cabin, mins from Red River Gorge
Campton
9.6 out of 10, Exceptional, (135 reviews)
"Away from busy towns and in an area where you can see the stars at night. Place was clean in arrival with sleeping arrangements as stated. Shower is nice and remodeled and enjoyable property to walk around and enjoy the scenery."
United States
Adam
The price is NZ$288
includes taxes & fees
11 Nov - 12 Nov
The Stillhouse Cabin, mins from Red River Gorge
A log cabin interior with a dining area, a sofa, a fireplace, and a television.

16. KNOTTY PINE•Cozy Cabin in RRG• Hot Tub •Fireplace •Pond for Fishing•Couples Love

KNOTTY PINE•Cozy Cabin in RRG• Hot Tub •Fireplace •Pond for Fishing•Couples Love
Pine Ridge
9.8 out of 10, Exceptional, (58 reviews)
"The cabin was easy to access and very clean. It was a great value. I booked this last minute for a solo trip to the area and was very pleased with everything. Thank you."
United States
Kim
The price is NZ$350
includes taxes & fees
15 Nov - 16 Nov
KNOTTY PINE•Cozy Cabin in RRG• Hot Tub •Fireplace •Pond for Fishing•Couples Love
A log cabin with a black door, a porch with chairs, and a small deck area.

17. 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 NZ$301
includes taxes & fees
9 Dec - 10 Dec
Cave Run Lodge - Near Lake - Playground & Fire pit - Cabin #6
Interior

18. 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, (344 reviews)
"great secluded property with everything we needed for a great weekend. Hot Tub was nice after a day of hiking."
United States
Kenneth
The price is NZ$509
includes taxes & fees
19 Nov - 20 Nov
Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods
A wooden cabin interior with a kitchen featuring a stove, microwave, and refrigerator.

19. Plum Crazy: Hot Tub Cabin in Frenchburg

Plum Crazy: Hot Tub Cabin in Frenchburg
3.0 star property
Frenchburg
10.0 out of 10, Exceptional, (4 reviews)
"This cabin was 100% the cleanest and nicest I’ve ever stayed in. Adorable, had everything needed for a comfortable stay. "
United States
Amy
The price is NZ$530
includes taxes & fees
11 Nov - 12 Nov
Plum Crazy: Hot Tub Cabin in Frenchburg
A small, dark-colored cabin with a gravel path leading to it, surrounded by trees and a string of lights.

20. Romantic Red River Gorge Cabin • Hot Tub • Quiet Escape

Romantic Red River Gorge Cabin • Hot Tub • Quiet Escape
Stanton
10.0 out of 10, Exceptional, (183 reviews)
"Loved the secluded atmosphere"
United States
Andrea
The price is NZ$454
includes taxes & fees
11 Nov - 12 Nov
Romantic Red River Gorge Cabin • Hot Tub • Quiet Escape
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.
View all properties

Find holiday rentals that suit your style

Apartment image
Apartments
Apartments
cabin image
Cabins
Cabins

Find out more about Montgomery County

Everything you need to know about Montgomery County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery County holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montgomery County holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montgomery County holiday rentals we have selected for you start as low as NZ$109 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 holiday 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 holiday.

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.