Williamsburg Holiday Rentals

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Holiday Rentals in Williamsburg

Frene Valley Guest House

10.0 out of 10, Exceptional, (77)
"The house is super cute and exactly as listed. It is SO convenient to downtown Hermann shopping and restaurants. Loved having off street parking for our group. Would definitely recommend for a weekend girls trip!"
Frene Valley Guest House

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

9.6 out of 10, Exceptional, (82)
"Great time wonderful town"
Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house

10.0 out of 10, Exceptional, (152)
"It was a great weekend in a cozy cottage "
The Stone Cottage, The Stone Cottage is a beautiful, spacious 3 bedroom, 3 bath house

Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!

9.8 out of 10, Exceptional, (42)
"Have stayed here twice now and will ALWAYS choose this house! Beautifully decorated home, ideal location in town, and hosts are the best! Great communication!"
Historic District Inn 4 Bed/ 3 Bath in the heart of downtown Hermann!

A Stunning Home, newly constructed & furnished

10.0 out of 10, Exceptional, (55)
"Beautiful home with private baths in every bedroom plus a guest bath. Excellent arrangement for adults coming together for our daughter's Wedding weekend. "
A Stunning Home, newly constructed & furnished

Cozy custom-built cabin - Lakeside

10.0 out of 10, Exceptional, (43)
"This is our second time staying at this property. Love the seclusion and peacefulness of being in the woods but still a short drive to shops and restaurants. "
Cozy custom-built cabin - Lakeside

The Farmhouse Inn: 3 bed, 3.5 whole house rental

10.0 out of 10, Exceptional, (93)
"What an adorable find! So many bathrooms!!! Great location with easy walking distance to many of the uptown shops and night life. The host was very responsive to messages. I would definitely stay here again!"
The price is AU$652
includes taxes & fees
1 Dec - 2 Dec
The Farmhouse Inn: 3 bed, 3.5 whole house rental

Ash Creek Guesthouse - Downtown Historic Hermann

10.0 out of 10, Exceptional, (41)
"We stayed for a weekend during Oktoberfest. We stayed up late playing games, we used the trolley to visit the wineries, and did a little shopping. "
The price is AU$716
includes taxes & fees
25 Nov - 26 Nov
Ash Creek Guesthouse - Downtown Historic Hermann

Cottage Properties - Country Log Cabin

10.0 out of 10, Exceptional, (154)
"Great hosts, very easy to talk to and accommodate our needs for the weekend. Will definitely book again for next year. "
Cottage Properties - Country Log Cabin

Wine Alley West Suite

9.2 out of 10, Wonderful, (35)
"Very comfortable stay. Wonderful town."
The price is AU$324
includes taxes & fees
25 Nov - 26 Nov
Wine Alley West Suite

Ash Creek Suite - In Downtown Historic Hermann

9.4 out of 10, Exceptional, (42)
"For 2 adults..great amount of space"
The price is AU$537
includes taxes & fees
25 Nov - 26 Nov
Ash Creek Suite - In Downtown Historic Hermann

Charming 1913 3 Bedroom 2 Bath Dutch Brick Haus

10.0 out of 10, Exceptional, (83)
"Loved this house. Able to walk to so many different places. Would definitely stay here again."
Charming 1913 3 Bedroom 2 Bath Dutch Brick Haus

The Artists Suites, Leonardo da Vinci Suite

9.8 out of 10, Exceptional, (28)
"The room was very cute located within a lovely building. Good walking distance from all the things. The patio and deck were nice. The street traffic from Market street was a little loud at night. Overall it was a nice trip. "
The Artists Suites, Leonardo da Vinci Suite

Modern Victorian - 1910 Guesthaus

10.0 out of 10, Exceptional, (25)
"The house is very clean and the beds are comfy!"
Modern Victorian - 1910 Guesthaus

The Bittersweet Inn: Brand new 6 bed 5 bath house

10.0 out of 10, Exceptional, (69)
"We could not have been happier with our stay at The Bittersweet Inn. The house was spotless, spacious, and bright. All furnishings are new and comfortable. The host was prompt with communication, friendly, and helpful. "
The Bittersweet Inn: Brand new 6 bed 5 bath house

Cozy Riverview Cottage. 5 minute walk to downtown

10.0 out of 10, Exceptional, (19)
"What an awesome place to visit. "
The price is AU$454
includes taxes & fees
25 Nov - 26 Nov
Cozy Riverview Cottage. 5 minute walk to downtown

The House on Wine Alley

9.0 out of 10, Wonderful, (36)
"Our annual girls’ trip to Hermann! This is the second time staying at this property! Very cute, great location. Had an issue with a toilet and texted the owner. Someone came with 30 min to fix. Definitely recommend the house on Wine Alley!"
The price is AU$501
includes taxes & fees
25 Nov - 26 Nov
The House on Wine Alley

Kork Haus - Whole house rental in Downtown Hermann

9.6 out of 10, Exceptional, (17)
"Absolutely great stay at the Kork Haus!"
The price is AU$716
includes taxes & fees
25 Nov - 26 Nov
Kork Haus - Whole house rental in Downtown Hermann

Suite on Schiller

9.8 out of 10, Exceptional, (96)
"Great location, very clean, but 1 bed was very hard was only negative. "
Suite on Schiller

Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO

10.0 out of 10, Exceptional, (130)
"The location was great. Everything within walking distance. "
Mozart House, Unique 3 bed 3.5 Bath House with Spectacular Outdoor Space in Downtown Hermann, MO
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.
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Other types of properties in Williamsburg you may be interested in

Baymont by Wyndham Fulton

2.5 star property
8.4 out of 10, Very good, (812)
"It was fair bang for the buck. Clean, quiet, freindly. About what I expected."
The price is AU$139
includes taxes & fees
2 Dec - 3 Dec
Baymont by Wyndham Fulton

Hermann Crown Suites

3.5 star property
9.4 out of 10, Exceptional, (637)
"If you need handicap accessible, do not rely on the description you need to call the property!!"
The price is AU$218
includes taxes & fees
28 Nov - 29 Nov
Hermann Crown Suites

Amerihost Inn & Suites Kingdom City

2.5 star property
6.4 out of 10, (216)
"Had a good stay, older property. Doesn't have all the "newest amenities" so it you are looking for that, may not be the place for you. I would stay there again. Staff was friendly and cost was a good value."
The price is AU$103
includes taxes & fees
25 Nov - 26 Nov
Amerihost Inn & Suites Kingdom City
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Williamsburg?

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

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

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!! : This holiday home rental outside of Williamsburg offers a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

What can I see and do in Williamsburg?

While you're exploring the area, Graham Cave State Park and Katy Trail - McKittrick Trailhead are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find William Woods University and Endless Summer Winery.

What are holiday rentals like in Williamsburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Williamsburg. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.