Best Vacation Homes in Montgomery County
Cabin
10.0(6 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $224/Night
7 Nights - US $1,571
House
9.5(2 Reviews)
1 Bedroom
1 Bath
4 Guests
796.53 ft²
- Pet Friendly
Parking
Air Conditioner
Internet
US $229/Night
7 Nights - US $1,604
Hotel
8.8(624 Reviews)
1 Bath
Pool
Breakfast- Kitchen
- Parking
US $153/Night
7 Nights - US $1,073
House
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $119/Night
7 Nights - US $833
House
2.0(1 Review)
2 Bedrooms
2 Baths
14 Guests
1636.11 ft²
Spa- Balcony/Terrace
- Pet Friendly
- Parking
US $273/Night
7 Nights - US $1,913
Apartment
9.8(12 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $144/Night
7 Nights - US $1,009
Cabin
9.6(26 Reviews)
2 Bedrooms
2 Baths
14 Guests
1632 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $219/Night
7 Nights - US $1,533
Apartment
9.6(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $146/Night
7 Nights - US $1,022
Montgomery County Luxury Rentals
House
9.2(10 Reviews)
7 Bedrooms
4 Baths
30 Guests
5000 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,793/Night
7 Nights - US $12,549
House
3 Bedrooms
3 Baths
5 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $287/Night
7 Nights - US $2,008
Cabin
9.6(5 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $227/Night
7 Nights - US $1,592
House
1 Bedroom
1 Bath
4 Guests
796.53 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $197/Night
7 Nights - US $1,379
House
2 Bedrooms
1 Bath
4 Guests
602.78 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $177/Night
7 Nights - US $1,239
House
1 Bedroom
1 Bath
4 Guests
53.82 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $150/Night
7 Nights - US $1,052
Cabin
9.2(71 Reviews)
2 Bedrooms
1 Bath
4 Guests
592 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $145/Night
7 Nights - US $1,012
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $140/Night
7 Nights - US $980
Montgomery County Pet Friendly Vacation Rentals
House
9.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $119/Night
7 Nights - US $833
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $169/Night
7 Nights - US $1,183
House
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $121/Night
7 Nights - US $849
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $74/Night
7 Nights - US $516
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $68/Night
7 Nights - US $476
Cabin
10.0(13 Reviews)
1 Bedroom
1 Bath
4 Guests
344 ft²
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
US $219/Night
7 Nights - US $1,536
Montgomery County Top Rated Vacation Rentals
Hotel
8.4(130 Reviews)
8 Baths
301.39 ft²
Private Pool- Fireplace/Heating
- Pool
- Breakfast
US $121/Night
7 Nights - US $845
US $113/Night
7 Nights - US $793
Hotel
7.8(197 Reviews)
1 Bath
- Private Pool
- Pool
- Parking
- Internet
US $98/Night
7 Nights - US $686
US $84/Night
7 Nights - US $590
Hotel
6.1(10 Reviews)
14 Baths
321.58 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $85/Night
7 Nights - US $595
Why Choose Rent By Owner for your Montgomery County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Montgomery County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination can greatly enhance your experience, as the area's climate and seasonal events offer unique opportunities for relaxation and exploration throughout the year.
Peak Season Highlights
Spring (March to May)
During spring, the area blooms with vibrant colors, making it an ideal time to enjoy scenic views and outdoor activities. Temperatures are mild and comfortable, perfect for exploring your vacation rentals.
Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
Fall (September to November)
Autumn brings stunning foliage and pleasant weather, attracting visitors seeking to experience the region’s natural beauty. This is a popular time to enjoy outdoor adventures from your vacation rental here.
Average Temperature Daytime: 65-70°F - Nighttime: 45-50°F
Off-Season Highlights
Winter (December to February)
During winter, the area experiences a quieter atmosphere with cooler temperatures, making it an excellent choice for those who prefer a peaceful retreat from their vacation rentals.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Summer (June to August)
Summertime offers warm weather ideal for outdoor relaxation, though this is a busier period for visitors. Booking your vacation rental here early will ensure a comfortable stay during peak season.
Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F
Weekly Weather Forecast for Montgomery County
How to Book Your Montgomery County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Montgomery County
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor grilling with a well-equipped barbecue area, perfect for gatherings in the region's scenic settings.
- Relax on private patios or verandas that offer picturesque views of the surrounding countryside.
- Make use of spacious yards or gardens ideal for outdoor activities and family fun in this inviting destination.
- Take advantage of outdoor dining spaces to savor meals under the open sky, surrounded by natural beauty.
- Explore nearby walking trails or nature paths accessible directly from your rental for outdoor adventure.
- Unwind in a private hot tub or spa area, providing a soothing retreat after exploring the area's attractions.
- Utilize outdoor fire pits or fireplaces for cozy evenings and memorable nights under the stars.
Top Attractions Around Montgomery County
What attractions are nearby?
Here, you can explore a variety of outdoor activities and local attractions that showcase the region’s natural beauty and cultural charm, making your stay in Montgomery County an enjoyable and memorable experience.
Family Activities
- Bluegrass Heritage Museum: Dive into the rich history of Montgomery County at this museum, offering engaging exhibits perfect for family learning adventures.
- KY River Adventures: Experience outdoor fun with kayaking and tubing along the Kentucky River, ideal for families seeking active pursuits in the region.
- Claysville Park: Enjoy picnicking, playgrounds, and scenic trails at this local park, making it a great spot for family outings and relaxing afternoons.
- Historic Downtown Mount Sterling: Stroll through charming streets filled with unique shops and eateries, offering a taste of the area's local culture and history.
Adult Activities
- Visit the Kentucky River Palisades: Explore this stunning natural formation, perfect for scenic drives and outdoor photography in the region.
- Discover local history at the Montgomery County Heritage Center: Gain insights into the area's rich past through engaging exhibits and historical displays.
- Enjoy outdoor recreation at the Bluegrass Community Park: Take advantage of walking trails, picnic areas, and sports facilities for a relaxing day outdoors.
- Experience local flavors through culinary tours: Sample authentic regional cuisine at various eateries that highlight the area's cultural heritage.
Other Places to Stay in Montgomery County, KY
Camargo
CHI Saint Joseph Health - Saint Joseph Mount Sterling
Jeffersonville
Mount Sterling
Montgomery County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the regional calendar to align your stay with festivals or markets that showcase the area's unique culture and enhance your experience.
- Explore Nearby Natural Settings: Take advantage of outdoor opportunities close to your rental to enjoy the region's scenic landscapes and fresh air.
- Opt for Central Locations: Choose accommodations situated near key attractions to maximize your sightseeing time and reduce travel hassle in this destination.
- Support Local Businesses: Engage with local eateries, shops, and markets during your visit to gain authentic insights into the area's vibrant community.
Transportation Options
- LexTran Bus Service: The local bus system offers convenient transportation around the city and nearby areas, making it easy for you to explore without a car in this region.
- Rental Cars: Numerous rental agencies operate here, providing flexible options to discover the region at your own pace during your stay.
- Taxi and Rideshare Services: Reliable taxi companies and rideshare options like Uber and Lyft are available for quick and hassle-free travel within the area.
- Public Transportation Infrastructure: The region is equipped with well-maintained public transit routes that connect key destinations, offering an affordable way to navigate here.
Local Customs Options
- Kentucky Bourbon Heritage:** You can explore the region's rich bourbon traditions, which influence local celebrations and hospitality in this area.
- Expect warm welcomes and friendly interactions that reflect the area's strong tradition of Southern politeness and community spirit.
- Enjoy the musical heritage of Kentucky, often showcased during community events and gatherings in the region.
- Participate in seasonal festivals and events that highlight local customs and bring residents and visitors together.
Montgomery County Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Montgomery County?
There are a lot of options in Montgomery County. If you plan on staying in the Montgomery County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Montgomery County:
- Rustic Mt. Sterling Cabin 1 Near Downtown Pets OK
- 1 Bedroom Bourbon House on the Hill
- Historic 2-Bedroom in Downtown
- Peaceful Mt Sterling Cabin: Deck & Fire Pit!
- Charming Downtown Apartment
- Rustic Mt. Sterling Cabin 2 Near Downtown Pets OK
- Rustic Mt Sterling Cabin1 Near Downtown Pets OK
- A Frame of Mind- Firepit, WiFi, Arcade, Pet Friendly
- Barn! 2-Hole Golf Course, BBall, Wiffleball, Soccer, Theater, Arcade, 2 Hot Tubs
- 5 o'clock somewhere in Mt Sterling
2. Which vacation homes in Montgomery County are best for families?
If you are looking for a family-friendly vacation home in Montgomery County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Montgomery County:
3. How many Rentbyowner vacation rentals are available in Montgomery County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 32 in the Montgomery County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Montgomery County.
4. What is the cancellation policy for vacation rentals in Montgomery County, Kentucky?
The cancellation policy varies by property; it is detailed in each listing. To ensure you understand the terms, please review the specific policy before booking or contact the property owner directly.
5. How do I confirm availability and book a vacation rental in the area?
Availability can be checked directly on the listing page. Once you find a suitable property, complete the booking through the platform, or reach out to the host if you have any questions about the reservation process.
6. Are there any additional fees or charges I should be aware of when booking here?
Additional fees such as cleaning, service charges, or taxes are typically included in the listing details. For clarity, review the total costs before finalizing your booking or contact the owner for a breakdown of all applicable charges.
7. What amenities and features are generally available in vacation rentals in this region?
Most properties offer essential amenities like Wi-Fi, parking, and fully equipped kitchens. Specific features vary by listing, so check each property's details to ensure they meet your needs.
8. Who should I contact if I have questions or need support during my stay in Montgomery County?
For any queries before or during your visit, contact the property owner or host listed on the booking platform. They are dedicated to providing a seamless and reliable experience in this destination.
