Winston Vacation Rentals

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Vacation 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."
$169 nightly
The price is $169
Sep 1 - Sep 2
Total with taxes and fees
The Deannie - Entire 2 Bedroom Apt in Quilt Town, USA

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. "
$135 nightly
The price is $135
Sep 1 - Sep 2
Total with taxes and fees
Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin

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."
$145 nightly
The price is $145
Sep 2 - Sep 3
Total with taxes and fees
Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.

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. "
$169 nightly
The price is $169
Sep 3 - Sep 4
Total with taxes and fees
The Irene - Entire 2 Bedroom Apt in Quilt Town, USA

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

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

8.0 out of 10, Very Good, (4)
"We had a great time spending two days at this property. The area is beautiful and the setup is so well thought out. The bed is surprisingly comfortable. We had a wonderful homestead breakfast one of the mornings. We will definitely return!"
$88 nightly
The price is $90
Sep 8 - Sep 9
Total with taxes and fees
Family/pet-friendly, quiet glamping getaway. Belle Tent/ Yurt out the Country.

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!"
$235 nightly
The price is $235
Sep 1 - Sep 2
Total with taxes and fees
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. "
$472 nightly
The price is $472
Oct 1 - Oct 2
Total with taxes and fees
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!

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. "
$187 nightly
The price is $187
Sep 1 - Sep 2
Total with taxes and fees
The Carolyn - 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

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."
$199 nightly
The price is $199
Sep 1 - Sep 2
Total with taxes and fees
The Bernice - Entire 2 Bedroom Apt in Quilt Town, USA

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. "
$207 nightly
The price is $212
Sep 6 - Sep 7
Total with taxes and fees
Modern Home in Gallatin

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.

Cameron Suites

4.0 star property
Cameron Suites

10 min from downtown Jamesport, MO

2.0 star property
10 min from downtown Jamesport, MO

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."
$169 nightly
The price is $169
Sep 1 - Sep 2
Total with taxes and fees
The Ingrid - Entire 2 Bedroom Apt in Quilt Town, USA
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston vacation 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 vacation.

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 vacation rentals in Winston?

Yes, you can find vacation rentals close to top points of interest in Winston, or you can go with a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Winston?

Modern Home in Gallatin : Visitors like this Winston vacation home rental. It 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 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 larger area, you’ll find Daviess County Courthouse and Cameron Veteran's Memorial Golf Glub.

What are vacation rentals like in Winston?

Vacation rentals are private accommodations you can stay in for a short or long stay in Winston. Vacation rentals feature extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family trips or small group gatherings.