Best Vacation Homes in Montgomery County
Cabin
10.0(48 Reviews)
1 Bedroom
1 Bath
2 Guests
625 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
R4,538/Night
7 Nights - R31,776
Apartment
1 Bedroom
1 Bath
2 Guests
699.65 ft²
- Fireplace/Heating
- Parking
Internet
Child Friendly
R3,459/Night
7 Nights - R24,205
Hotel
9.2(959 Reviews)
1 Bath
Hot Tub
Pool- Balcony/Terrace
Breakfast
R2,033/Night
7 Nights - R14,234
Cabin
10.0(9 Reviews)
4 Bedrooms
2 Baths
10 Guests
1650 ft²
Private Pool- Hot Tub
Spa- Fireplace/Heating
R11,306/Night
7 Nights - R79,149
House
1 Bedroom
1 Bath
2 Guests
1108.68 ft²
- Fireplace/Heating
- Parking
Air Conditioner- Internet
R3,039/Night
7 Nights - R21,271
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R3,198/Night
7 Nights - R22,389
House
10.0(1 Review)
2 Bedrooms
1 Bath
8 Guests
288 ft²
- Child Friendly
R2,898/Night
7 Nights - R20,282
Apartment
9.8(55 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
- Parking
R2,390/Night
7 Nights - R16,731
Montgomery County Luxury Rentals
House
7 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R49,934/Night
7 Nights - R349,538
Other
10.0(75 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R6,539/Night
7 Nights - R45,767
Other
10.0(4 Reviews)
4 Bedrooms
1 Bath
11 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R5,493/Night
7 Nights - R38,456
Condo
9.0(14 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R2,732/Night
7 Nights - R19,131
Hotel
8.7(196 Reviews)
9 Baths
322.92 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
R2,638/Night
7 Nights - R18,466
Hotel
9.0(170 Reviews)
1 Bath
373.66 ft²
- Private Pool
Oceanfront- Fireplace/Heating
- Pool
R2,411/Night
7 Nights - R16,877
Hotel
8.7(218 Reviews)
1 Bath
247.57 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R2,133/Night
7 Nights - R14,932
R1,917/Night
7 Nights - R13,424
Montgomery County Pet Friendly Vacation Rentals
Apartment
9.8(16 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Child Friendly
R1,539/Night
7 Nights - R10,781
Hotel
7.4(294 Reviews)
1 Bath
413.34 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R1,797/Night
7 Nights - R12,581
House
10.0(1 Review)
5 Bedrooms
3 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R7,906/Night
7 Nights - R55,349
Hotel
4.8(142 Reviews)
7 Baths
204.51 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R1,135/Night
7 Nights - R7,944
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pet Friendly
R1,021/Night
7 Nights - R7,150
R9,727/Night
7 Nights - R68,092
RV Rental
1 Bedroom
1 Bath
6 Guests
- Pet Friendly
- Parking
- Child Friendly
Security/Safety
R2,043/Night
7 Nights - R14,299
Montgomery County Large Vacation Homes
House
10.0(1 Review)
5 Bedrooms
3 Baths
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R13,910/Night
7 Nights - R97,371
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?
Timing your visit to the area can enhance your experience, so consider planning your stay during the season when local events and weather conditions align with your preferences for a memorable getaway in Montgomery County, Indiana.
Peak Season Highlights
Summer (June to August)
During the peak summer months, you'll experience warm weather ideal for outdoor activities and exploring the area. This is when the region sees an influx of visitors seeking a lively and vibrant atmosphere.
Average Temperature Daytime: 85°F - Nighttime: 65°F
Fall (September to November)
Autumn brings mild temperatures and colorful foliage, making it a popular time for sightseeing and outdoor pursuits in the region. Expect busier weekends as visitors enjoy the scenic landscape.
Average Temperature Daytime: 70°F - Nighttime: 50°F
Off-Season Highlights
Winter (December to February)
The winter months tend to be quieter, offering a peaceful retreat with cooler temperatures and fewer crowds. It’s an excellent time to enjoy indoor activities or scenic winter views.
Average Temperature Daytime: 40°F - Nighttime: 25°F
Early Spring (March to April)
In early spring, the area experiences a lull in visitors before the full bloom of the season, creating a tranquil atmosphere. You might find more flexible options for booking your stay during this period.
Average Temperature Daytime: 55°F - Nighttime: 35°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 areas perfect for preparing meals amidst scenic surroundings.
- Relax in private patios or decks with comfortable seating to unwind after a day of exploring.
- Take advantage of spacious yards ideal for outdoor games and family activities.
- Make use of on-site fire pits for cozy evenings under the stars.
- Access nearby walking trails or bike paths that showcase the natural beauty of the area.
- Benefit from included outdoor furniture designed for alfresco dining and lounging.
- Explore well-maintained gardens or landscaped grounds that enhance your outdoor experience here.
Top Attractions Around Montgomery County
What attractions are nearby?
While staying here, you can explore a variety of outdoor activities and local attractions that showcase the charm of Montgomery County, Indiana, offering a perfect blend of relaxation and adventure for your getaway.
Family Activities
- Turkey Run State Park: Discover scenic hiking trails and outdoor adventures amidst rugged landscapes right in the region.
- Corydon Capitol State Historic Site: Step back in time at this historic site that offers family-friendly tours and educational experiences about Indiana's history.
- Clifty Falls State Park: Enjoy breathtaking waterfalls, nature walks, and picnic spots perfect for relaxing family outings nearby.
- Madison: Explore charming streets, local museums, and riverfront activities that make for a memorable family day in this picturesque town.
Adult Activities
- Visit the Indiana War Memorials: You can explore the region’s rich history by touring memorials dedicated to Indiana veterans, offering a meaningful experience in Montgomery County.
- Explore Civilian Museums and Historic Sites: Delve into local heritage through museums and historic landmarks that showcase the area's past, ideal for history enthusiasts staying in nearby vacation rentals.
- Enjoy Outdoor Recreation at Local Parks: In your time here, relax and unwind by engaging in outdoor activities such as hiking, picnicking, or birdwatching at scenic parks within the area.
- Attend Community Festivals and Events: Experience the local culture and hospitality by participating in annual festivals or community gatherings hosted throughout the region.
Other Places to Stay in Montgomery County, IN
Lapland
Waveland
Waynetown
New Market
Linden
Ladoga
Shades State Park
Darlington
Crawfordsville Aquatic Center
Yountsville
Crawfordsville
Montgomery County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the area’s event calendar when booking your vacation rentals to make the most of local festivals or markets during your stay.
- Explore Outside the Main Attractions: Use your vacation rentals as a comfortable base to discover hidden gems and scenic spots in the region beyond popular destinations.
- Choose a Strategic Location: Select properties close to key attractions or outdoor activities to maximize your time exploring and minimize travel time around this destination.
- Engage with the Community: Take advantage of the friendly local atmosphere by visiting nearby shops, eateries, and parks to enrich your experience in the area.
Transportation Options
- Montgomery County Transit System: Offers convenient local bus services that make exploring the area easy during your stay.
- Amtrak Stations in nearby Lafayette: Provides regional train options connecting you to other parts of Indiana and beyond.
- Private Car Rentals: Available through several providers, giving you flexible transportation to visit the region's attractions at your own pace.
- Taxis and Rideshare Services: Easily accessible in this destination for quick trips within the county or to neighboring areas.
Local Customs Options
- Community Events and Festivals: Participating in local festivals and community events allows you to immerse yourself in the area's welcoming spirit and celebrate its traditions.
- Historical Preservation: Respect for historic sites and architecture is a cherished custom, reflecting the region’s appreciation for its rich past.
- Local Cuisine Appreciation: Enjoying regional dishes at neighborhood eateries highlights the area's unique culinary heritage and hospitality.
- Outdoor Recreation Etiquette: Observing outdoor customs such as fishing, hiking, and boating etiquette ensures harmony with nature and local residents here.
Frequently Asked Questions About Montgomery County?
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:
- 115 year old farmhouse renovated completely 2014, on 4 acres
- Yurt inspired Cabin at The Queen & I Homestead
- Sugar Creek Cabin w/Nordic spa bordering 2 state parks!
- Charming historic home centrally located in Crawfordsville, near Wabash
- Modern Elegance: Timeless Crawfordsville Studio!
- Kozy Kodiak Camper in Beautiful Crawfordsville
- Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly
- Home away from home!
- Holiday Inn Express Hotel & Suites Crawfordsville by IHG
- Hampton Inn & Suites Crawfordsville
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 38 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?
Cancellation policies vary depending on the individual property listing. You should review the specific cancellation terms outlined in the rental details or contact the property owner directly to understand any fees or restrictions before booking.
5. Are there any additional fees I should be aware of when booking a vacation rental in the area?
Additional fees such as cleaning, service charges, or security deposits may apply and are typically listed during the booking process. Confirm these details by reviewing the listing information or reaching out to the host to ensure transparency.
6. How do I ensure my dates are available before proceeding with the reservation?
Availability can be checked directly on the listing page by selecting your desired dates. If you have questions about availability or need assistance, contacting the property owner can help clarify booking options.
7. Is it possible to modify or extend my stay once I've made a reservation?
Modifications or extensions depend on the property's policies and availability. It’s best to contact the host directly after booking to discuss any changes to your reservation.
8. Are there any specific house rules or requirements I should know about before staying in this destination?
Many listings specify house rules regarding smoking, pets, or noise levels. Review the property description carefully and communicate with the owner if you have any special requirements or questions about the rules.
Montgomery County Top Rated Vacation Rentals
R1,652/Night
7 Nights - R11,559
Hotel
8.4(1004 Reviews)
1 Bath
- Spa
- Fireplace/Heating
- Pool
- Breakfast
R1,698/Night
7 Nights - R11,884
Other
9.8(89 Reviews)
2 Bedrooms
2 Baths
9 Guests
1350 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
R4,249/Night
7 Nights - R29,750
Cabin
9.6(125 Reviews)
3 Bedrooms
2 Baths
8 Guests
1836 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
R9,808/Night
7 Nights - R68,659
