Discover Your Perfect Montgomery County Vacation Homes

Montgomery County Pet Friendly Vacation Rentals

9.8 (4 Reviews)
Apartment
Suite 39 North
  • Air Conditioner
  • Parking
  • Pet Friendly
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New
House
Historic Hope Chapel
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
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See More Pet-Friendly Vacation Rentals in Montgomery County on PetFriendly.io

Why Choose Rent By Owner for your Montgomery County Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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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

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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
autumn
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

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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
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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

More Top-Rated Vacation Rentals in Montgomery County Area

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.

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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.
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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

Shades State Park
Shades State Park Vacation Rentals
Lapland
Lapland Vacation Rentals
Linden
Linden Vacation Rentals
Alamo
Alamo Vacation Rentals
New Market
New Market Vacation Rentals
Waynetown
Waynetown Vacation Rentals
Darlington
Darlington Vacation Rentals
New Richmond
New Richmond Vacation Rentals
Wingate
Wingate Vacation Rentals
Crawfordsville Aquatic Center
Crawfordsville Aquatic Center Vacation Rentals
Crawfordsville
Crawfordsville Vacation Rentals
Waveland
Waveland Vacation Rentals
More Places to Stay Near Montgomery County

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:

2. How many vacation rentals have private pools in Montgomery County?

There are 28 vacation rentals with private pools near Montgomery County. Top-rated RBO homes that have access to a swimming pool include:

3. 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:

4. How many Rentbyowner vacation rentals are available in Montgomery County?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 536 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. 

5. 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.

6. 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.

7. 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.

8. 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.

9. 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.