Default HTG hotel image

Montgomery City Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Montgomery City holiday rentals

1. The Mercantile on the Katy Trail

The Mercantile on the Katy Trail
4.5 star property
Hermann
9.8 out of 10, Exceptional, (36 reviews)
"It’s an absolute must do! Such a cool little town right on the Katy Trail!"
United States
Weston
The price is NZ$351
includes taxes & fees
8 Sept - 9 Sept
The Mercantile on the Katy Trail

2. Country Container Tiny House. Experience peace by the water & native wildlife!

Country Container Tiny House. Experience peace by the water & native wildlife!
Fulton
10.0 out of 10, Exceptional, (34 reviews)
"The home was clean and it was a great stay!"
United States
Stephanie P.
The price is NZ$253
includes taxes & fees
27 Aug - 28 Aug
Country Container Tiny House. Experience peace by the water & native wildlife!

3. 3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck

3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
Hermann
9.6 out of 10, Exceptional, (15 reviews)
"Host was very accommodating, property perfect, I can't say enough good things about our stay."
United States
Susan R.
The price is NZ$612
includes taxes & fees
27 Aug - 28 Aug
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck

4. McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann

McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann
McKittrick
10.0 out of 10, Exceptional, (2 reviews)
"Loved this placed, would definitely come back!"
United States
Cody W.
The price is NZ$458
includes taxes & fees
1 Sept - 2 Sept
McKittrick Suite - Loft Stay on Katy Trail in Historic Mercantile, 4 min Hermann

5. Papa's Cabin - 40 acres & 5 acre lake!

Papa's Cabin - 40 acres & 5 acre lake!
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"Overall stay was amazing! The property was just like described and the hostess was easy to communicate with."
United States
Prisilla B.
The price is NZ$342
includes taxes & fees
1 Sept - 2 Sept
Papa's Cabin - 40 acres & 5 acre lake!

6. Large Unique 2-Bedroom Gamed Themed Loft

Large Unique 2-Bedroom Gamed Themed Loft
Fulton
9.8 out of 10, Exceptional, (48 reviews)
"Great place to stay! We have stayed here several times and it’s always been great! "
United States
chris w.
The price is NZ$353
includes taxes & fees
27 Aug - 28 Aug
Large Unique 2-Bedroom Gamed Themed Loft

7. Downtown Hermann Small Batch Suite with Sidewalk Swagger at Lionheart Distillery

Downtown Hermann Small Batch Suite with Sidewalk Swagger at Lionheart Distillery
Hermann
10.0 out of 10, Exceptional, (1 review)
The price is NZ$490
includes taxes & fees
27 Aug - 28 Aug
Downtown Hermann Small Batch Suite with Sidewalk Swagger at Lionheart Distillery

8. Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!

Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!
Hermann
10.0 out of 10, Exceptional, (63 reviews)
"Loved this stay for our girls trip!! So nice and clean! Would definitely rent again!"
United States
Lauren
The price is NZ$850
includes taxes & fees
27 Aug - 28 Aug
Historic Downtown Hermann Getaway-Walk to Wineries, Shops and Restaurants!

9. Ash Creek Guesthouse - Downtown Historic Hermann

Ash Creek Guesthouse - Downtown Historic Hermann
Hermann
9.8 out of 10, Exceptional, (52 reviews)
"Great place for our crew. Rode the Katy Trail and experienced Hermann. Very clean and well taken care of. Highly recommend. "
United States
Mark
The price is NZ$621
includes taxes & fees
27 Aug - 28 Aug
Ash Creek Guesthouse - Downtown Historic Hermann

10. Archie’s House

Archie’s House
Berger
10.0 out of 10, Exceptional, (37 reviews)
"House was perfect for our girl’s trip"
United Kingdom
Monica A.
The price is NZ$836
includes taxes & fees
27 Aug - 28 Aug
Archie’s House

11. Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook

Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook
Hermann
10.0 out of 10, Exceptional, (6 reviews)
"This place is AMAZING. It is beautiful and such a peaceful get away. Just a quick 5 minute drive to town, but you feel like you’re miles away. The property was beautiful and the space was peaceful and secluded. Highly recommend. "
United States
Patti
The price is NZ$446
includes taxes & fees
27 Aug - 28 Aug
Cozy Wooded Retreat 3 minutes from Hermann ~ Nature`s Nook

12. Germantown Inn & Lounge

Germantown Inn & Lounge
Hermann
10.0 out of 10, Exceptional, (3 reviews)
"We had a very pleasant stay. From check in, to check out, it was all perfect!"
United States
Jennifer A.
The price is NZ$345
includes taxes & fees
30 Aug - 31 Aug
Germantown Inn & Lounge

13. Charming 2-bedroom house in fabulous downtown Hermann

Charming 2-bedroom house in fabulous downtown Hermann
Hermann
9.6 out of 10, Exceptional, (14 reviews)
"Had a great time here-very responsive hosts-clean,quiet-just perfect for our stay!"
United States
Carrie Jean
The price is NZ$493
includes taxes & fees
27 Aug - 28 Aug
Charming 2-bedroom house in fabulous downtown Hermann

14. Wine Alley West Suite

Wine Alley West Suite
Hermann
9.0 out of 10, Wonderful, (57 reviews)
"Nice location, tan out of hot water, but nice clean!! "
United States
Melissa B.
The price is NZ$359
includes taxes & fees
27 Aug - 28 Aug
Wine Alley West Suite

15. Wine Alley East suite

Wine Alley East suite
Hermann
9.4 out of 10, Exceptional, (85 reviews)
"Host was great. Easy checkin and checkout. Great location to ride trolley to wineries and then walk Hermann at night."
United States
Sandy H.
The price is NZ$359
includes taxes & fees
27 Aug - 28 Aug
Wine Alley East suite

16. Cozy Riverview Cottage. 5 minute walk to downtown

Cozy Riverview Cottage. 5 minute walk to downtown
Hermann
10.0 out of 10, Exceptional, (57 reviews)
"Great stay! The cottage was super cute"
United States
Tim C.
The price is NZ$451
includes taxes & fees
27 Aug - 28 Aug
Cozy Riverview Cottage. 5 minute walk to downtown

17. The House on Wine Alley

The House on Wine Alley
Hermann
9.2 out of 10, Wonderful, (66 reviews)
"We enjoyed the perfect location"
United States
Don O.
The price is NZ$536
includes taxes & fees
27 Aug - 28 Aug
The House on Wine Alley

18. Queen Bed|Smk|Kingdom City, MO

Queen Bed|Smk|Kingdom City, MO
Kingdom City, MO
10.0 out of 10, Exceptional, (41 reviews)
"Free WiFi worked well throughout my stay, a definite plus."
United States
Anonymous traveller
The price is NZ$126
includes taxes & fees
27 Aug - 28 Aug
Queen Bed|Smk|Kingdom City, MO

19. Plenty room for relaxing and downtown location to walk around!

Plenty room for relaxing and downtown location to walk around!
Hermann
10.0 out of 10, Exceptional, (20 reviews)
"Great location. We were repeat guests. Laura and her husband always go above and beyond. We love it there. "
United States
Julie I.
The price is NZ$432
includes taxes & fees
27 Aug - 28 Aug
Plenty room for relaxing and downtown location to walk around!

20. Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries

Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
Hermann
10.0 out of 10, Exceptional, (4 reviews)
"So pretty and perfect for our weekend."
United States
Katherine B.
The price is NZ$458
includes taxes & fees
1 Sept - 2 Sept
Depot Suite - Ground-Floor Historic Loft on Katy Trail, 4 Mins to Hermann Wineries
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Montgomery City Hotel Reviews

Find out more about Montgomery City

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Montgomery City holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Montgomery City. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Montgomery City. Seeing all the best attractions is bound to make you fall in love with Montgomery City. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Montgomery City short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Montgomery City?

Yes, there are holiday rentals close to the most popular sights in Montgomery City, or you can select a more secluded option if you're looking for a relaxing stay. Montgomery City is known for its parks.

What are some of the best holiday rentals that Montgomery City has to offer?

Cozy Riverview Cottage. 5 minute walk to downtown: This holiday home rental outside of Montgomery City is equipped with a patio, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Montgomery City?

While you're exploring the area, Graham Cave State Park and Daniel Boone Conservation Area are a couple of picturesque spots to get outside and enjoy nature. Endless Summer Winery and Katy Trail - McKittrick Trailhead are a couple of places you'll find in the wider area.

What’s a holiday rental in Montgomery City like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montgomery City. Holiday rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for families.