Gerald Vacation 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 Gerald vacation rentals

10.0 out of 10, Exceptional, (218 reviews)
"This was a great getaway. Hosts were so nice and their dog was sweet! My little dog and I had a great stay. Thabk you!"
United States
Tiffany P.
The price is CA $158
CA $233 total
includes taxes & fees
Mar 4 - Mar 5
Cozy Cottage, we're told it's heavenly!
10.0 out of 10, Exceptional, (46 reviews)
"Wonderful property, clean and very quiet!"
United States
Lindsay J.
The price is CA $101
CA $209 total
includes taxes & fees
Mar 9 - Mar 10
TJ’s Country Getaway- Dog Friendly
9.8 out of 10, Exceptional, (26 reviews)
"our workers enjoyed their stay "
United States
Chris P.
The price is CA $85
CA $192 total
includes taxes & fees
Mar 4 - Mar 5
RGM Farms Guesthouse, rural tranquil setting for family & friends to enjoy.

Vacation Home in Washington

Cozy Historic WashMo home
9.2 out of 10, Wonderful, (27 reviews)
"Lovely stay, well done on the updates of the house. Upstairs is a little cold, but otherwise it was a great weekend rental. Close to the river, so easy walking "
United States
Valerie R.
The price is CA $138
CA $335 total
includes taxes & fees
Mar 5 - Mar 6
Cozy Historic WashMo home

Vacation Home in Canaan Township

Tiny Home A at Red Oak Valley
The price is CA $239
CA $285 total
includes taxes & fees
Mar 4 - Mar 5
Tiny Home A at Red Oak Valley
10.0 out of 10, Exceptional, (61 reviews)
"Amazing host, clean easy access. Will stay here again if available"
United States
Jeanie S.
The price is CA $166
CA $346 total
includes taxes & fees
Mar 4 - Mar 5
Cozy little house blocks from the Park & Fair Grounds. EV Charger equipped.
10.0 out of 10, Exceptional, (43 reviews)
"Beautifully relaxing cabin! Can’t wait to stay again and explore more of the area. Perfect get-away!"
United States
Carrie K.
The price is CA $142
CA $216 total
includes taxes & fees
Mar 11 - Mar 12
Lake Cabin near the Bourbeuse River
10.0 out of 10, Exceptional, (27 reviews)
"Clean place very comfortable. We had a very relaxing stay and would definitely stay again. Relaxing hot tub. "
United States
Brian
The price is CA $374
CA $457 total
includes taxes & fees
Mar 4 - Mar 5
Featured on USA Today - Hot tub, Fenced Yard
The price is CA $130
CA $450 total
includes taxes & fees
Mar 4 - Mar 5
Unique Tiny Home! Lakefront ~ BBQ Grill ~ Couple's Retreat
10.0 out of 10, Exceptional, (18 reviews)
"This is a beautiful place , well equipped kitchen . It was very clean too . It has located downtown and many restaurants in walking distance"
United States
Johanna D.
The price is CA $356
CA $454 total
includes taxes & fees
Mar 4 - Mar 5
Tamm Loft | River view, Downtown WashMo, Dog-friendly
The price is CA $365
CA $507 total
includes taxes & fees
Mar 4 - Mar 5
Lost Hill Lake Sunshine Skoolie, The Sunshine Skoolie - Lost Hill Lake
3.5 star property
8.0 out of 10, Very good, (1 review)
"Great communication, had a couple of leaks and shower flooded but the maintenance came right away to fix it. Overall clean, AC/Heat unit in each room, big kitchen, wonderful sitting area and decor."
United States
Stacy
The price is CA $236
CA $693 total
includes taxes & fees
Mar 9 - Mar 10
Wine Country Getaway | JZ Vacation Rentals

Vacation Home in New Florence

Secluded 2 bedroom home close to Hermann
9.8 out of 10, Exceptional, (46 reviews)
"Very nice place "
United States
Yaqui S.
The price is CA $246
CA $347 total
includes taxes & fees
Mar 4 - Mar 5
Secluded 2 bedroom home close to Hermann

Vacation Home in Washington

Washington Guest House
10.0 out of 10, Exceptional, (44 reviews)
"Very spacious, comfortable and well appointed property. Conveniently located to everything we needed. Very much enjoyed our stay there. Host kept us informed before, during, and after our stay."
United States
Randy B.
The price is CA $251
CA $494 total
includes taxes & fees
Mar 4 - Mar 5
Washington Guest House
9.6 out of 10, Exceptional, (7 reviews)
"The home was very clean and had everything we needed. Very quiet area out in the country. Enjoyed our stay there and would highly recommend staying there."
United States
Sheri D.
The price is CA $276
CA $503 total
includes taxes & fees
Mar 4 - Mar 5
3-bedroom family friendly home on 4 acres near Hermann with WiFi, AC, deck
3.0 star property
The price is CA $499
CA $716 total
includes taxes & fees
Mar 5 - Mar 6
Spacious Ozarks Family Home - Private Pool & Grill
10.0 out of 10, Exceptional, (96 reviews)
"Awesome little property with everything you could need. Owners were so attentive. We will definitely go back! "
United States
Dana B.
The price is CA $353
CA $431 total
includes taxes & fees
Mar 4 - Mar 5
Katy Haus: Hot tub, Wineries, Fenced yard, Dog-friendly
10.0 out of 10, Exceptional, (118 reviews)
"Nice property, with great view of Hermann"
United States
Mike L.
The price is CA $135
CA $221 total
includes taxes & fees
Mar 4 - Mar 5
Gipfel Suite - Himmel Haus Bed & Breakfast
4.5 star property
9.8 out of 10, Exceptional, (28 reviews)
"Great place, fully stocked and clean!"
United States
Lauren
The price is CA $302
CA $324 total
includes taxes & fees
Mar 4 - Mar 5
The Mercantile on the Katy Trail
10.0 out of 10, Exceptional, (47 reviews)
"We especially enjoyed the lovely outdoor patios, and the location."
United States
Sallie S.
The price is CA $648
CA $1,197 total
includes taxes & fees
Mar 4 - Mar 5
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Gerald Hotel Reviews

Find out more about Gerald

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Gerald. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Gerald?

Yes, we have vacation rentals close to well known points of interest in Gerald, or you can go with a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Gerald?

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!! : This vacation home rental outside of Gerald offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

What’s there to see and do in Gerald?

While you're exploring the area, Meramec Caverns and Goose Island are a couple of picturesque spots to get outside and enjoy nature. Bommarito Estate Almond Tree Winery and Jesse James Wax Museum are a couple of places you'll find in the larger area.

What’s a vacation rental in Gerald like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Gerald. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.