Best Vacation Homes in Montgomery
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
7 Guests
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $149/Night
7 Nights - US $1,044
House
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
602.78 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
Parking
US $392/Night
7 Nights - US $2,747
US $100/Night
7 Nights - US $699
Cabin
10.0(187 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Parking
US $199/Night
7 Nights - US $1,394
House
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
602.78 ft²
Oceanfront- Hot Tub
- Fireplace/Heating
- Ocean View
US $432/Night
7 Nights - US $3,026
Cabin
10.0(67 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $380/Night
7 Nights - US $2,659
House
10.0(50 Reviews)
5 Bedrooms
3 Baths
13 Guests
Private Pool- Hot Tub
- Fireplace/Heating
Pool
US $605/Night
7 Nights - US $4,235
House
10.0(36 Reviews)
4 Bedrooms
1 Bath
10 Guests
3500 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $761/Night
7 Nights - US $5,330
Montgomery Luxury Rentals
House
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
Child Friendly
Laundry
Bedding/Linens
US $722/Night
7 Nights - US $5,055
Ski Chalet
1 Bedroom
1 Bath
2 Guests
602.78 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- View
US $359/Night
7 Nights - US $2,514
House
10.0(23 Reviews)
3 Bedrooms
3 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $350/Night
7 Nights - US $2,450
House
3 Bedrooms
1 Bath
11 Guests
1614.59 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
Air Conditioner
US $342/Night
7 Nights - US $2,393
Cabin
10.0(34 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $341/Night
7 Nights - US $2,389
House
9.8(11 Reviews)
1 Bedroom
1 Bath
2 Guests
602.78 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Parking
US $337/Night
7 Nights - US $2,360
Cabin
10.0(13 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $328/Night
7 Nights - US $2,299
Cabin
1 Bedroom
1 Bath
2 Guests
600 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $311/Night
7 Nights - US $2,174
Montgomery Pet Friendly Vacation Rentals
Cabin
9.4(3 Reviews)
3 Bedrooms
1 Bath
5 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $204/Night
7 Nights - US $1,426
House
2 Bedrooms
2 Baths
7 Guests
1700.7 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $121/Night
7 Nights - US $847
House
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $173/Night
7 Nights - US $1,210
House
3 Bedrooms
1 Bath
5 Guests
1205.56 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
Internet
US $180/Night
7 Nights - US $1,262
New
House
2 Bedrooms
4 Baths
14 Guests
3304.52 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $270/Night
7 Nights - US $1,890
Hotel
8.9(305 Reviews)
5 Baths
487.06 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $136/Night
7 Nights - US $952
Hotel
7.8(76 Reviews)
6 Baths
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $127/Night
7 Nights - US $892
Montgomery Large Vacation Homes
House
10.0(17 Reviews)
3 Bedrooms
1 Bath
11 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $307/Night
7 Nights - US $2,148
House
10.0(1 Review)
7 Bedrooms
3 Baths
14 Guests
3500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $299/Night
7 Nights - US $2,092
House
9.4(13 Reviews)
3 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $156/Night
7 Nights - US $1,093
House
10.0(75 Reviews)
6 Bedrooms
5 Baths
26 Guests
3500 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $892/Night
7 Nights - US $6,242
Why Choose Rent By Owner for your Montgomery 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
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as seasonal conditions and local events in Montgomery influence the best period for a memorable getaway in this region.
Peak Season Highlights
Spring (March to May)
During spring, the area experiences mild temperatures and blooming landscapes, making it an ideal time to enjoy outdoor activities and scenic views.
Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
Fall (September to November)
In fall, the region showcases vibrant foliage and comfortable weather, perfect for exploring local attractions and relaxing in your vacation rentals.
Average Temperature Daytime: 65-70°F - Nighttime: 45-50°F
Off-Season Highlights
Winter (December to February)
Winter brings cooler temperatures and quieter surroundings, offering a peaceful retreat with fewer crowds at your vacation rentals here.
Average Temperature Daytime: 30-45°F - Nighttime: 20-30°F
Summer (June to August)
Summers can be hot and humid, but it's also when this destination sees fewer visitors, providing a more relaxed experience in the region’s rental properties.
Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F
Weekly Weather Forecast for Montgomery
How to Book Your Montgomery 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
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 savoring the region’s fresh air and scenic views.
- Relax in private patios or decks that provide a tranquil space to unwind after exploring the area.
- Take advantage of spacious yards suited for outdoor activities or family gatherings.
- Make use of outdoor grills to prepare delicious meals while enjoying the region’s pleasant climate.
- Explore nearby walking trails or nature paths accessible directly from your rental property.
- Unwind by the fire pits designed for cozy evenings under the stars in this destination.
- Utilize outdoor sports equipment such as bikes or kayaks available on-site or nearby for adventure seekers.
Top Attractions Around Montgomery
What attractions are nearby?
In the nearby area, you can enjoy a variety of outdoor activities and local attractions that showcase the natural beauty and charm of this destination, making it an ideal spot for a memorable getaway.
Family Activities
- Montgomery County Fairgrounds: Enjoy family-friendly events and seasonal activities that bring the community together in this vibrant part of the region.
- Historic Montgomery City Courthouse: Explore the local history with a visit to this well-preserved landmark, offering insight into the area's past through informative exhibits.
- Ozark Trail Nature Preserve: Spend quality time outdoors hiking, picnicking, or simply soaking in the scenic beauty at this peaceful natural retreat nearby.
- Riverfront Park: Engage in outdoor fun by the water with playgrounds, walking trails, and spots perfect for family gatherings right here in the area.
Adult Activities
- Explore the Montgomery County Museum: Discover local history and culture through engaging exhibits that offer insights into this area's unique heritage.
- Visit the Mississippi Riverfront: Enjoy scenic views and peaceful strolls along the river, ideal for relaxing and taking in the natural beauty of the region.
- Experience the area's outdoor trails: Hike or bike through nearby nature paths that showcase the lush landscapes and wildlife characteristic of this destination.
- Enjoy local festivals and events: Participate in community celebrations that highlight regional traditions, food, and entertainment here in the region.
Other Places to Stay in Montgomery, MO
Montgomery City
Montgomery Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take the time to discover the area’s unique attractions and scenic spots to enrich your stay in Montgomery's charming surroundings.
- Plan Outdoor Activities: Maximize your visit by engaging in outdoor pursuits such as fishing, hiking, or boating, which are popular here and highlight the region’s natural beauty.
- Experience Regional Cuisine: Savor authentic local flavors at nearby eateries or prepare meals at your vacation rentals to enjoy the region’s culinary delights.
- Check Seasonal Events: Stay informed about seasonal festivals or events happening during your stay to fully immerse yourself in the local culture and community.
Transportation Options
- Montgomery County Transit: This regional transit service offers convenient bus routes designed to connect travelers with key destinations within the area.
- Private Car Rentals: Renting a car here provides the flexibility to explore scenic spots and local attractions at your own pace, making it an ideal option for easy transportation around this destination.
- Taxi and Rideshare Services: Available throughout the region, these on-demand options provide quick and reliable transportation for short trips or when you prefer not to drive yourself.
- Cycling and Walking: For a more leisurely experience, many areas are pedestrian-friendly and suitable for biking, allowing you to enjoy the scenery while getting around.
Local Customs Options
- Local Dining Etiquette: When visiting here, you'll find that sharing meals and engaging in friendly conversation are integral parts of the regional dining customs.
- Community Events: Participating in local festivals and gatherings is a cherished tradition, reflecting the area's close-knit community spirit.
- Respect for Nature: Appreciating the natural surroundings by practicing environmentally conscious habits is highly valued throughout the region.
- Historical Respect: Honoring local history through respectful behavior at landmarks and during cultural events helps preserve the area's heritage.
Montgomery Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Montgomery?
There are a lot of options in Montgomery. If you plan on staying in the Montgomery 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:
- Cottage Properties - Country Log Cabin
- Cozy custom-built Cabin - Lakeside
- Spacious Five Bedroom Country Home Near Hermann MO
- Two-House Private Country Retreat - 4 Bedrooms and 3.5 Baths
- Treehouse - Sunrise
- Quiet Country 3 Bedroom Escape in Jonesburg MO
- 4K Ranch - 10 acre property & home near Hermann
- Treehouse - Twilight
- Cozy Farmhouse Retreat in Truxton - 2 bedrooms available
- The Venue at Hermann
2. Which vacation homes in Montgomery are best for families?
If you are looking for a family-friendly vacation home in Montgomery, 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:
3. How many Rentbyowner vacation rentals are available in Montgomery?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 42 in the Montgomery 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.
4. What is the cancellation policy for vacation rentals in Montgomery, Missouri?
Cancellation policies vary by property, so it’s best to review the specific listing details or contact the host directly to understand the terms and any applicable fees.
5. Are there any additional fees I should be aware of when booking a rental in Montgomery, Missouri?
Additional fees such as cleaning charges, service fees, or security deposits are often listed upfront on each property’s page. Be sure to check the listing details or reach out to the owner for clarification.
6. How do I ensure the property I choose in this destination is suitable for my needs?
Each listing provides detailed descriptions, amenities, and photos. You can also contact the host to ask specific questions about the property’s suitability for your stay.
7. What is the process for securing my reservation in Montgomery, Missouri?
Reservations are confirmed once you complete the booking through the platform, after which you will receive confirmation details from the host. It’s recommended to read the property rules and requirements carefully before finalizing.
8. Is it possible to modify or cancel my booking if my plans change?
Modification and cancellation options depend on the individual property’s policies. Check the listing’s cancellation policy or contact the owner directly to discuss your situation.
Montgomery Top Rated Vacation Rentals
Other
5.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $199/Night
7 Nights - US $1,393
