Montgomery County holiday rentals

We found 170 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Montgomery County that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as a fireplace and garden. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Popular Montgomery County destinations on Stayz

Holiday rentals with weekly discounts – Montgomery County

Showing deals for:25 Dec - 1 Jan

Interior
Interior
Dining
Back yard fenced in swimming pool.  This pool does have a deep end.
Wonderful
(25 reviews)

Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.

Warrenton

8% off
AU$6,012
for 7 nights, 1 home
AU$859 per night
includes taxes & fees
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.
Fully stocked kitchen with refrigerator, stove, cooktop, microwave & Keurig
Front door with bench and outdoor light
Property grounds
Exterior
Exceptional
(22 reviews)

Treehouse - Twilight

Jonesburg

8% off
AU$3,583
for 7 nights, 1 cabin
AU$512 per night
includes taxes & fees
Treehouse - Twilight
Exterior
Private kitchen
Terrace/patio
Private kitchen
Exceptional
(26 reviews)

Quiet Country 3 Bedroom Escape in Jonesburg MO

Jonesburg

9% off
AU$3,674
for 7 nights, 1 home
AU$525 per night
includes taxes & fees
Quiet Country 3 Bedroom Escape in Jonesburg MO
Front and Side view with Fire Pit chairs
Front of Cottage
Stairs
View of Kitchen and Primary Bathroom / Laundry entry on left
Exceptional
(34 reviews)

A Charming and Private Cottage in the historic downtown of Hermann, Missouri.

Hermann

12% off
AU$3,491
for 7 nights, 1 cottage
AU$499 per night
includes taxes & fees
A Charming and Private Cottage in the historic downtown of Hermann, Missouri.
Outdoor dining
Dining
Living area
King bedroom downstairswith full bathroom
Exceptional
(41 reviews)

7th Heaven Guesthouse

Hermann

33% off
AU$4,505
for 7 nights, 1 home
AU$644 per night
includes taxes & fees
7th Heaven Guesthouse
Outdoor dining
Exterior
Private kitchen
Living area
Exceptional
(7 reviews)

Claus Haus Guest House

Hermann

8% off
AU$5,426
for 7 nights, 1 home
AU$775 per night
includes taxes & fees
Claus Haus Guest House
Kitchen
Basement sitting area and Bedroom #5
Bedroom #5 with two full Bathrooms.
Basement sitting area.
Exceptional
(85 reviews)

Newly remodeled home in Historic Hermann Wine Counrtry.

Hermann

8% off
AU$5,585
for 7 nights, 1 home
AU$798 per night
includes taxes & fees
Newly remodeled home in Historic Hermann Wine Counrtry.
Large deck area.
Below a coffee cafe. Ceiling has a sound proof lining. Open 7am-5 pm
Large living room.
Evergreen around the corner from us. Drinks and small plates
Exceptional
(91 reviews)

SPACIOUS HISTORIC DOWNTOWN LOFT! BEST LOCATION IN THE HEART OF TOWN!

Hermann

17% off
AU$3,048
for 7 nights, 1 room
AU$435 per night
includes taxes & fees
SPACIOUS HISTORIC DOWNTOWN LOFT! BEST LOCATION IN THE HEART OF TOWN!
Exterior detail
Terrace/patio
Dining
Private kitchen
Exceptional
(22 reviews)

Whole House Rental -In the Heart of Historic Hermann, Missouri

Hermann

8% off
AU$4,343
for 7 nights, 1 home
AU$620 per night
includes taxes & fees
Whole House Rental -In the Heart of Historic Hermann, Missouri
Living area
Outdoor dining
Interior
Dining
Exceptional
(53 reviews)

Helen's House-3 bed, 2 bath bungalow 3 blocks from Main Street!!!

Hermann

8% off
AU$3,877
for 7 nights, 1 home
AU$554 per night
includes taxes & fees
Helen's House-3 bed, 2 bath bungalow 3 blocks from Main Street!!!
Exterior
Private kitchen
Interior
Room
Exceptional
(49 reviews)

Modern Victorian - 1910 Guesthaus

Hermann

8% off
AU$2,955
for 7 nights, 1 home
AU$422 per night
includes taxes & fees
Modern Victorian - 1910 Guesthaus

Find the perfect holiday rental for your Montgomery County getaway

Learn about the unique charm of Montgomery County with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Montgomery County

Are you searching for top things to see and do while you're in town? Venture out of your cosy holiday rental and check out everything that makes Montgomery County a fun spot to go on holiday. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Endless Summer Winery (12.2 mi / 19.6 km)
  • Hermannhof Vineyards (19.1 mi / 30.8 km)
  • Stone Hill Winery (19.7 mi / 31.7 km)
  • OakGlenn Vineyards and Winery (20.1 mi / 32.3 km)
  • Adam Puchta & Son Winery (21.3 mi / 34.3 km)
  • Bias Winery (23 mi / 36.9 km)

Exploring the natural landscape of Montgomery County

Whether you're an active traveller or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Montgomery County. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Graham Cave State Park (6.2 mi / 9.9 km)
  • The Pinnacle (11.2 mi / 18 km)
  • Daniel Boone Conservation Area (15.1 mi / 24.3 km)
  • Katy Trail - McKittrick Trailhead (17.1 mi / 27.6 km)
  • Kitzbuhl Lake (26.9 mi / 43.2 km)
  • Inverness Beach (27.2 mi / 43.7 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Montgomery County?
The most desirable types of holiday homes in Montgomery County are farmhouses. After something a little different? Stayz has many options to match our guests' requirements, so you'll see properties in all shapes and sizes. The perfect home away from home is waiting for you — discover yours today.
How much does it cost to rent a holiday home in Montgomery County?
Season, property type and length of stay are some things that can affect the price of a holiday home. Simply enter your dates of travel to find the ultimate escape. From cosy country cottages to sprawling luxury villas, all Stayz holiday homes offer terrific value.
How much does it cost to rent a beach house in Montgomery County?
When you travel and the size and style of the property will help determine the cost of your beachside stay. Type in your Montgomery County travel dates to view your options on Stayz. Can't live without a hot tub? Use the filters to select the amenities and features you want in your beach house.
What are popular home amenities in Montgomery County?
When it comes to home amenities that people are searching for in Montgomery County, an oven, a microwave oven and a fridge are at the top of the list. With Stayz holiday homes, you'll enjoy choices to match your taste and style, whether you're going on a trip with your partner, family members or even pets.
Are there large group holiday homes in Montgomery County?
You can choose from three properties in Montgomery County that can host 10 or more guests. Whether you're planning a trip with extended family or an event like a birthday party, there's ample space to get your group together under the same roof.
What are the top attractions for families in Montgomery County?
There are loads of awesome things to see and do with the family in Montgomery County, such as:
  • Graham Cave State Park
  • New Florence United Methodist Church
  • Shrine of Our Lady of Sorrows
Are there holiday homes with WiFi in Montgomery County?
There are seven holiday homes with WiFi in Montgomery County. If you'd like to disconnect from daily life on your escape, but still want to be connected to the web, these getaways are just what you need. Narrow your search by applying the WiFi filter on Stayz.
How old do you have to be to rent a holiday home in Montgomery County?
You'll have to check with the Montgomery County holiday home you're considering on Stayz as age restrictions vary. However, typically it's 16, 18 or 21.
How long can I rent a holiday home in Montgomery County for?
It's really down to the Montgomery County property. To see all available options offering extended stays, just enter your travel dates and number of guests into Stayz. Enjoy having the entire place to yourself, along with comforts such as a fully-equipped kitchen and a yard where the kids can run around and play. Keep your eyes peeled for any long-term stays that offer discounted weekly or monthly prices.

More holiday ideas