Best Vacation Homes in Montgomery County
House
10.0(24 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
R2,166/Night
7 Nights - R15,162
House
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
785.77 ft²
- Fireplace/Heating
Parking
Internet
Child Friendly
R2,511/Night
7 Nights - R17,569
Hotel
9.6(593 Reviews)
1 Bath
Pool- Balcony/Terrace
Breakfast- Kitchen
R2,413/Night
7 Nights - R16,897
House
10.0(18 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
R1,988/Night
7 Nights - R13,917
Apartment
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
661.98 ft²
Private Beach
Oceanfront
Ocean View- Balcony/Terrace
R2,079/Night
7 Nights - R14,556
House
10.0(13 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R3,852/Night
7 Nights - R26,967
Apartment
10.0(3 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R2,863/Night
7 Nights - R20,041
House
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
784 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R1,693/Night
7 Nights - R11,854
Montgomery County Luxury Rentals
House
3 Bedrooms
2 Baths
6 Guests
1334.72 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R3,340/Night
7 Nights - R23,381
House
9.4(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R3,297/Night
7 Nights - R23,087
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,210/Night
7 Nights - R22,464
House
3 Bedrooms
2 Baths
6 Guests
1330 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
R3,159/Night
7 Nights - R22,121
House
9.8(20 Reviews)
2 Bedrooms
1 Bath
5 Guests
1150 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,056/Night
7 Nights - R21,384
Hotel
9.1(154 Reviews)
8 Baths
301.39 ft²
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
R2,849/Night
7 Nights - R19,943
House
9.8(18 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,759/Night
7 Nights - R19,321
House
1 Bedroom
1 Bath
2 Guests
753.47 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
R2,271/Night
7 Nights - R15,899
Montgomery County Pet Friendly Vacation Rentals
House
10.0(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,354/Night
7 Nights - R16,472
Hotel
8.6(112 Reviews)
1 Bath
271.25 ft²
- Private Pool
- Oceanfront
Hot Tub- Fireplace/Heating
R1,835/Night
7 Nights - R12,837
Hotel
7.2(159 Reviews)
1 Bath
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
R1,350/Night
7 Nights - R9,448
House
10.0(13 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R1,785/Night
7 Nights - R12,493
Hotel
7.9(194 Reviews)
1 Bath
319.33 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
R1,474/Night
7 Nights - R10,315
House
9.0(7 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
R1,891/Night
7 Nights - R13,230
Hotel
7.8(308 Reviews)
5 Baths
389.66 ft²
- Private Pool
- Oceanfront
- Hot Tub
Spa
R1,564/Night
7 Nights - R10,954
House
2 Bedrooms
1 Bath
5 Guests
1198 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
R1,736/Night
7 Nights - R12,149
Montgomery County Top Rated Vacation Rentals
Hotel
9.0(649 Reviews)
1 Bath
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
R1,898/Night
7 Nights - R13,279
R1,621/Night
7 Nights - R11,347
Hotel
8.4(1003 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
R1,657/Night
7 Nights - R11,592
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 ensures you can enjoy the best weather and local events, making your stay in Montgomery County, Illinois, USA, truly memorable and well-suited to your preferences.
Peak Season Highlights
Late Spring to Early Summer (May to June)
This period offers warm weather ideal for exploring the area’s scenic beauty and outdoor activities, making it a popular time to book vacation rentals.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Early Fall (September to October)
The region experiences pleasant temperatures and vibrant fall foliage, attracting travelers seeking comfortable weather and picturesque landscapes.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Mid Winter (January to February)
During this quieter time, you can enjoy more affordable rates and less crowded attractions while experiencing cooler temperatures in the region.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
Late Autumn (November)
As the weather begins to cool, fewer visitors choose this time, providing an opportunity for a peaceful retreat with lower accommodation costs.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 50°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 dining areas perfect for soaking up the region's scenic views.
- Relax in private patios or decks that offer a comfortable space to unwind outdoors.
- Make the most of spacious yards ideal for outdoor activities and family gatherings.
- Take advantage of well-maintained gardens showcasing local flora and greenery.
- Use outdoor grills to prepare delicious meals while enjoying the fresh air.
- Benefit from nearby walking trails or nature paths that highlight the area's natural beauty.
- Spend time on inviting porches or verandas that provide a charming outdoor setting.
Top Attractions Around Montgomery County
What attractions are nearby?
Explore nearby outdoor activities, scenic parks, and local attractions that make this area an ideal spot for outdoor enthusiasts and adventure seekers staying in Montgomery County, Illinois.
Family Activities
- Montgomery County Fairgrounds: Engage in family-friendly events and seasonal festivals that showcase the local community spirit of this region.
- Commonwealth Park: Enjoy outdoor activities such as picnicking, playground fun, and walking trails within this scenic park suitable for all ages.
- Beall Woods State Park: Discover nature through hiking and wildlife observation in this serene park that offers educational programs for kids and adults alike.
- Local Museums and Historic Sites: Explore the area's rich history with interactive exhibits and guided tours that provide an engaging experience for families seeking culture and education.
Adult Activities
- Historic Downtown Montgomery County: Explore charming shops, local eateries, and historic sites that give you a glimpse into the area's rich heritage.
- Recreational Parks and Nature Reserves: Enjoy outdoor activities like hiking, picnicking, or birdwatching in scenic parks nestled within this welcoming region.
- Local Wineries and Breweries: Sample regional wines and craft beers while learning about the area's vibrant craft beverage scene.
- Cultural Events and Festivals: Participate in annual festivals that celebrate the region’s history and community spirit, providing memorable experiences during your stay.
Other Places to Stay in Montgomery County, IL
Coalton
Ohlman
Coffeen
Donnellson
Waggoner
Walshville
Farmersville
Hillsboro
Taylor Springs
Raymond
Litchfield
North Litchfield Township
Montgomery County Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining and attractions: Take advantage of the area's authentic eateries and unique attractions to fully immerse yourself in the regional culture during your stay.
- Plan outdoor activities ahead: The region offers scenic parks and natural spaces, so scheduling outdoor adventures like hiking or picnicking can enhance your visit.
- Choose accommodations wisely: Opt for centrally located vacation rentals that offer easy access to the region's key sites and conveniences for a more comfortable experience.
- Connect with local events and festivals: Check the calendar for seasonal events happening in the area, giving you a chance to enjoy local traditions and community gatherings.
Transportation Options
- Montgomery County Transit: Provides reliable bus services across the area, making it easy for you to explore local attractions from your vacation rental.
- Regional Airport: Offers convenient air travel options for visitors arriving from different parts of the country, connecting you quickly to this welcoming destination.
- Car Rental Services: Numerous providers in the region allow you to rent a vehicle, giving you flexibility to discover Montgomery County and its surroundings at your own pace.
- Taxi and Ride-Sharing: Widely available throughout here, these transportation options offer quick and affordable ways to get around during your stay.
Local Customs Options
- Local Festivals and Events: Participating in community festivals showcases the region's vibrant culture and welcoming spirit here in Montgomery County.
- Traditional Amish Practices: Respect for Amish customs, including their craftsmanship and farming traditions, is an integral part of experiencing the area's heritage.
- Historical Preservation: Visiting historical sites reflects the area's commitment to maintaining its rich history and understanding local narratives.
- Southern Illinois Hospitality: Embracing the warm hospitality typical in this part of Illinois enhances your stay and connection with the community 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:
- Edwards House; Litchfield, IL; Pets welcome
- Our Little House In Litchfield
- State Street House; 3-br house; PETS WELCOME; Litchfield
- Loft Living - Small Town Charm n3-bedroom loft in beautiful Downtown Litchfield
- Charming Hillsboro Home Less Than 1 Mi to Downtown!
- The Lakehouse by Historic Red Rooster
- Charming Hillsboro Home < 1 Mi to Downtown!
- The Relaxing House - Quiet 2 Bedroom Home
- Harrison House; Litchfield, IL; Pets welcome
- Route 66 house; Litchfield IL; Pets welcome
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 36 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, Illinois?
Cancellation policies vary depending on the individual property listing. You should review the specific terms on the listing page or contact the property owner directly to understand the cancellation and refund options available for your stay.
5. How do I ensure my booking is secure when reserving a vacation rental in this area?
Booking through a trusted platform provides secure payment options and verified listings. Always confirm the host’s credentials and read reviews to ensure a safe and reliable reservation experience.
6. Are there any additional fees I should be aware of when booking a vacation rental in the region?
Additional fees such as cleaning charges, service fees, or local taxes may apply. These details will be outlined during the booking process or on the property’s listing page, so review them carefully before confirming your reservation.
7. What amenities are typically included with vacation rentals in this destination?
Most vacation rentals offer standard amenities like Wi-Fi, fully equipped kitchens, and parking. To find accommodations with specific features, check the property descriptions and reach out to the owner if you have special requirements.
8. Can I make special requests or modifications to my booking for a vacation rental in Montgomery County, Illinois?
Special requests can often be accommodated, but it’s best to contact the property owner directly after booking to discuss any modifications or additional needs to ensure they can be met during your stay.
