Winston Holiday Rentals

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Holiday Rentals in Winston

The Deannie - Entire 2 Bedroom Apt in Quilt Town, USA

9.8 out of 10, Exceptional, (51)
"Nicely located in a quiet neighborhood. Just a walking distance away from Missouri Star Quilt Company. Clean and nicely decorated."
The price is AU$261
includes taxes & fees
10 Sept - 11 Sept
The Deannie - Entire 2 Bedroom Apt in Quilt Town, USA

Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.

10.0 out of 10, Exceptional, (4)
"Nice , clean , quiet, place to spend the night."
The price is AU$225
includes taxes & fees
6 Sept - 7 Sept
Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.

Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin

10.0 out of 10, Exceptional, (3)
"Cute little home. Just right for a couple stay. Everything was clean, and smelled fresh. Cute little town, we would stay again. "
The price is AU$209
includes taxes & fees
7 Sept - 8 Sept
Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin

Quilter's retreat! 3 quilting spaces and 2 full bathrooms!

9.8 out of 10, Exceptional, (30)
"A great place to stay it was clean. It was easy to get to had a great time. "
Quilter's retreat! 3 quilting spaces and 2 full bathrooms!

The Bird's Nest - 2 bedroom House

10.0 out of 10, Exceptional, (17)
"Property location was perfect."
The Bird's Nest - 2 bedroom House

The Irene - Entire 2 Bedroom Apt in Quilt Town, USA

10.0 out of 10, Exceptional, (33)
"The property was so nice and close to downtown. We will definitely stay there again when in town. "
The price is AU$261
includes taxes & fees
7 Sept - 8 Sept
The Irene - Entire 2 Bedroom Apt in Quilt Town, USA

Family/pet-friendly, quiet glamping getaway. Belle Tent/ Yurt out the Country.

8.4 out of 10, Very good, (5)
"Such a beautiful experience at this property! Everything we needed was already there for us. We had such a great time getting away from the hustle and bustle. "
The price is AU$141
includes taxes & fees
15 Sept - 16 Sept
Family/pet-friendly, quiet glamping getaway. Belle Tent/ Yurt out the Country.

The Bernice - Entire 2 Bedroom Apt in Quilt Town, USA

9.8 out of 10, Exceptional, (16)
"Great apartment to stay while visiting The Missouri Star Quilt Co. Close to shopping. Nice to have a well stocked kitchen because close restaurants are scarce. Very nice grocery store right downtown. Tidy with comfortable beds. Plenty of closet space and easy parking. Would stay here again."
The price is AU$307
includes taxes & fees
6 Sept - 7 Sept
The Bernice - Entire 2 Bedroom Apt in Quilt Town, USA

8th Street Haven - House in DT Hamilton

9.6 out of 10, Exceptional, (14)
"We loved being able to sew and cook and hang out in the open space. It was a nice little space."
8th Street Haven - House in DT Hamilton

The Carolyn - Entire 2 Bedroom Apt in Quilt Town, USA

10.0 out of 10, Exceptional, (16)
"A wonderful place to stay. It felt like coming home at the end of our busy days. Reasonably priced and so much value for the cost. "
The price is AU$289
includes taxes & fees
30 Sept - 1 Oct
The Carolyn - Entire 2 Bedroom Apt in Quilt Town, USA

Enjoy this spacious ranch-style house next to the quilting capital of the world.

9.8 out of 10, Exceptional, (7)
"The Hughes House is a very welcoming & homey place to stay. Quiet neighborhood & 2 minutes from Quilt Town. Plenty of restaurants in the area for meals & grocery store as well. The hosts communicated quickly to any questions we had & made us feel at home. Very clean as well. We would stay again."
Enjoy this spacious ranch-style house next to the quilting capital of the world.

Secluded cabin on farmland with fire pit, pond, a/c & treehouse

2.0 star property
9.8 out of 10, Exceptional, (9)
"Property was amazing and relaxing. Host was super helpful and quick communication when I needed help. Highly recommend, just as described and pictured. "
Secluded cabin on farmland with fire pit, pond, a/c & treehouse

Hamilton Getaway -Entire House in DT Hamilton

10.0 out of 10, Exceptional, (45)
"Very clean and comfortable. Just make sure to bring your own shampoo/soap!"
The price is AU$363
includes taxes & fees
6 Sept - 7 Sept
Hamilton Getaway -Entire House in DT Hamilton

1920s Restored Home-walk to MSQC shops, Quilt Town USA

10.0 out of 10, Exceptional, (1)
"Very clean, lots of room, well furnished kitchen. It was like being in a new model home. Very close to the quilt shops, easy walk. Great communication with the owners! Check-in was a breeze! Would definitely stay there again. "
The price is AU$733
includes taxes & fees
1 Oct - 2 Oct
1920s Restored Home-walk to MSQC shops, Quilt Town USA

Cameron Nature Retreat: Hike, Bike & More!

2.5 star property
Cameron Nature Retreat: Hike, Bike & More!

The Ingrid - Entire 2 Bedroom Apt in Quilt Town, USA

9.4 out of 10, Exceptional, (24)
"We enjoyed out two night stay - It was a stopping point for us with bonus quilt shopping day."
The price is AU$261
includes taxes & fees
7 Sept - 8 Sept
The Ingrid - Entire 2 Bedroom Apt in Quilt Town, USA

The Delores - Entire 2 Bedroom Apt in Quilt Town, USA

9.8 out of 10, Exceptional, (37)
"Great place to stay for shopping, classes, and Missouri Star Events. Clean, easy access and reasonably priced."
The price is AU$307
includes taxes & fees
12 Sept - 13 Sept
The Delores - Entire 2 Bedroom Apt in Quilt Town, USA

4-bdrm: Near Adam-Ondi-Ahman, MO Star Quilt, Jamesport Amish, Squirrel Cage Jail

4-bdrm: Near Adam-Ondi-Ahman, MO Star Quilt, Jamesport Amish, Squirrel Cage Jail

Modern Home in Gallatin

9.6 out of 10, Exceptional, (22)
"This was a beautifully renovated home. Super easy check in. Nice, spacious open floor plan. Very clean and comfortable. Great extras like the seating on the back porch, and the amazing shower in the master bedroom. Would absolutely recommend anyone to stay here when visiting Gallatin. "
The price is AU$327
includes taxes & fees
6 Sept - 7 Sept
Modern Home in Gallatin

10 min from downtown Jamesport, MO

2.0 star property
10 min from downtown Jamesport, 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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Top Winston Hotel Reviews

Find out more about Winston

Find out more about Winston

Everything you need to know about Winston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winston holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winston. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winston holiday rentals we have selected for you start as low as AU$141 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winston holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Winston?

Yes, there are holiday rentals close to the most popular sights in Winston, 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 Winston has to offer?

Modern Home in Gallatin : This holiday home rental outside of Winston is equipped with a selection of games, air conditioning and laundry facilities to help you feel comfortable during your stay. 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.

What can I see and do in Winston?

While you're exploring the area, Dockery Park and Lake Allaman are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Daviess County Courthouse and Cameron Veteran's Memorial Golf Glub.

What are holiday rentals like in Winston?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winston. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a family trip.