Montgomery County Vacation Rentals from CA $145: Short-Term Rentals for 2026

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

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Our top choices for Montgomery County vacation rentals

A Farmers' Market pavilion with a green signboard, white structural elements, and a covered area with yellow bollards.

1. Cozy, Bright Home in Historic Downtown

Mount Sterling

Glenda

CA $177 total

includes taxes & fees

Sep 30 - Oct 1

A building with a staircase leading to a door marked with the number 218.

2. 1 Bedroom Bourbon House on the Hill

Mount Sterling

Anne D.

CA $186 total

includes taxes & fees

Sep 30 - Oct 1

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

Mount Sterling

Trey S.

CA $193 total

includes taxes & fees

Sep 30 - Oct 1

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

Mount Sterling

"Clean, unexpected amenities provided in case you forgot something. Ceiling fans in living room and bedroom. Recently renovated. The sweet treats in the fridge upon check in, both local, were a nice touch and paired well with coffee in the morning. Walkable to a nice local bar and grill, downtown area, was a bonus. 5 minutes to I-64. About a half an hour or less to Red River Gorge/ Natural Bridge if you are going hiking. Pet friendly. WiFi. We would definitely stay here again!"

Dan S.

A bedroom with a bed, a ceiling fan, a TV, and large windows.

5. New, Cozy, Secluded Cabin

Jeffersonville

Edgar O.

CA $273 total

includes taxes & fees

Sep 30 - Oct 1

6. Hunting Lodge in the City

Mount Sterling

CA $200 total

includes taxes & fees

Oct 3 - Oct 4

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

7. Natural Bridge State Resort Park

Slade

Monty

CA $145 total

includes taxes & fees

Sep 30 - Oct 1

A wooden deck with blue chairs overlooking a river and forested hills.

8. Furnished Glamping Tent/2 Queen Beds/Red River Access- Soaring Eagle - #7

Stanton

kayla

CA $186 total

includes taxes & fees

Sep 30 - Oct 1

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Top Montgomery County Hotel Reviews

Best Western Winchester Hotel

10/10 Excellent

"Staff was friendly and helpful. Breakfast was good. Ample parking. My room was very clean."

Black Bear Lodge Motel

8/10 Good

"It is a super cute and in a great spot close to everything. When we got there the lights and plugs weren’t working. The staff was on it though and fixed the issue fast. The place was so clean. The coffee maker wasn’t working properly. The bed was horrible. Now I know that’s probably not a big deal for some but man. We only got two flat pillows but at the request of more they brought them fast. I do love it but not sure if I will go back until they get a way better mattress. Price was reasonable also."

Higher Standards-RRG-Hot Tub- Hand Crafted Detail

8/10 Good

"Amazing cabin in a beautiful serene setting. Cabin is custom built with unique detail. We were disappointed with the grill situation - we were not able to use it, as it was filthy inside and falling apart. We had purchased nice steaks and chicken to grill and had to change plans. Hot tub was very nice, cabin was very clean. I would recommend the owners provide more cookware, spray cleaner for kitchen cleanup, and also maybe stock cards and games for rainy days or families. The fire pit and chairs are great, but would recommend stocking a bit of covered firewood, lighters, a flash light, and bug spray. Overall I would recommend the cabin - it is beautiful!"

Secluded Cabin has its own private waterfall, hot tub and wi-fi

8/10 Good

"My husband and I loved this little cabin. It’s quiet and very private. We definitely would stay here again. Things you should know, 14 wheel or front wheel drive would probably be best. 2The water is from a well so it’s a bit sulfur smelling but it did great things for skin and hair! 3The oven racks are rusty, so get aluminum foil so you can get a take and bake pizza from Miguel’s. It’s delicious! 4If you don’t like steps, you’re in trouble 5You must have BBQ from Thatchers and a show at the pit house. The owners were immediately old friends. 6If you’re looking for “convenience “ this is not your place. It’s removed and wonderful and needs to stay that wayAbout the house The bed was big and very comfortable and it was so nice to have the hot tub accessible only from the loft. It made it very private. Two bathrooms is definitely a bonus. The “stairs” and rails are a great touch. It’s definitely easier to come down backwards. There are some basic maintenance needs but I have those at my house as well so you’ll be fine. Go do something outside like ride that steep ass chair lift. Hike down if you can. It’s magical."

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 $145 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.

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Montgomery County vacation rentals

1. Cozy, Bright Home in Historic Downtown

2. 1 Bedroom Bourbon House on the Hill

3. 5 o'clock somewhere in Mt Sterling

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

5. New, Cozy, Secluded Cabin

6. Hunting Lodge in the City

7. Natural Bridge State Resort Park

8. Furnished Glamping Tent/2 Queen Beds/Red River Access- Soaring Eagle - #7

9. The Cozy Den

10. Mountaintop Cottage

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

12. Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.

13. Serene Retreat, Private Setting, Near Muir Valley Climbing & Redpoint BBQ

14. Larkspur Cabin with Hot Tub near Red River Gorge

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

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

17. Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion

18. "Stars Hollow" Cozy Mini Cabin Stay - RRG

19. Plum Crazy: Frenchburg Cabin on 1 Acre

20. Red River Gorge Turtle Falls Hot Tub Firepit Wi-Fi

Find vacation rentals that suit your style

Top Montgomery County Hotel Reviews

Best Western Winchester Hotel

Ramada Limited Mount Sterling

Black Bear Lodge Motel

Comfort Inn Winchester

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

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

Higher Standards-RRG-Hot Tub- Hand Crafted Detail

TURNING LEAF•Cozy Cabin in the RRG• Couples Retreat

Secluded Cabin has its own private waterfall, hot tub and wi-fi

Find out more about Montgomery County