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, (18)
"We stayed here for a few days and had a great time. The location can't be beat if you are looking for something close to all the Missouri star quilt shops. It's just a block away and we walked most everywhere in town which was nice. The apartment was very nice and very clean. The beds were a little soft for us but by no means does that change this review rating as that is a personal preference to have a firmer mattress. The only issue we had was using the door lock but our host responded quickly...
The price is NZ$275
includes taxes & fees
9 Jun - 10 Jun
The Deannie - Entire 2 Bedroom Apt in Quilt Town, USA
Relaxing spacious home in Quilt Town USA
10.0 out of 10, Exceptional, (3)
"We had a fantastic time and the accommodations were perfect! Lots of room and the individual quilting stations were so awesome. We got to shop all day and quilt into the evening. Totally recommend staying here!"
Relaxing spacious home in Quilt Town USA
The Gingerbread House in Quilt Town, USA!
10.0 out of 10, Exceptional, (51)
"Great place to meet up for a girlfriend week at MSQC. Friends from coast to Rocky Mountains meet to visit Hamilton MO. Hamilton quilt museum was great, worth the time seeing the history. Fun time shopping. The Gingerbread house was perfect for friends to hang out and catch up on old time and tell stories."
The price is NZ$585
includes taxes & fees
5 Jun - 6 Jun
The Gingerbread House in Quilt Town, USA!
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Modern Home in Gallatin
9.4 out of 10, Exceptional, (3)
"Stayed here overnight on the way down to Arkansas. Great space inside, very clean and organized. Loved having a fenced yard for our dog to run around outside. Would absolutely recommend!"
The price is NZ$311
includes taxes & fees
4 Jul - 5 Jul
Modern Home in Gallatin
Comfortable Two-Story Family Home in Picturesque Small Town USA
9.8 out of 10, Exceptional, (80)
"Thank you, we had a good time"
The price is NZ$467
includes taxes & fees
13 Jun - 14 Jun
Comfortable Two-Story Family Home in Picturesque Small Town USA
The Irene - Entire 2 Bedroom Apt in Quilt Town, USA
9.8 out of 10, Exceptional, (20)
"Went to spend the week at MSQC. It was a bucket list girls trip and it was everything dreamed it to be. Also, the quilt museum was amazing!"
The price is NZ$273
includes taxes & fees
12 Jun - 13 Jun
The Irene - Entire 2 Bedroom Apt in Quilt Town, USA
Hamilton Getaway -Entire House in DT Hamilton
10.0 out of 10, Exceptional, (41)
"We were very comfortable and enjoyed our stay very much. Our stay was over a weekend and even though most of the stores were closed on Sunday, we needed a down day and time to refresh."
The price is NZ$381
includes taxes & fees
6 Jun - 7 Jun
Hamilton Getaway -Entire House in DT Hamilton
The Betty Blue, Quilt Town, USA!
10.0 out of 10, Exceptional, (23)
"We enjoyed are stay in this sweet little house. The kitchen was well equipped and had everything we needed. Only wish there were better pillows for the beds. I would stay here again."
The price is NZ$464
includes taxes & fees
25 Jun - 26 Jun
The Betty Blue, Quilt Town, USA!
Gallatin Get-Away Bungalow Perfect for quilters, hunters, or families!
The price is NZ$339
includes taxes & fees
4 Jul - 5 Jul
Gallatin Get-Away Bungalow Perfect for quilters, hunters, or families!
The Bird's Nest - 2 bedroom House
10.0 out of 10, Exceptional, (1)
"This house is close to the Missouri Star stores and is within walking distance. The owners are very responsive. I enjoyed my stay."
The Bird's Nest - 2 bedroom House
Cameron Nature Retreat: Hike, Bike & More!
Cameron Nature Retreat: Hike, Bike & More!
The Ingrid - Entire 2 Bedroom Apt in Quilt Town, USA
10.0 out of 10, Exceptional, (16)
"We enjoyed out two night stay - It was a stopping point for us with bonus quilt shopping day."
The price is NZ$273
includes taxes & fees
15 Jun - 16 Jun
The Ingrid - Entire 2 Bedroom Apt in Quilt Town, USA
Piper's Place - 2 Bedroom House in DT Hamilton
9.4 out of 10, Exceptional, (3)
"Lovely place and great communication. My only suggestion would be to put something on the shower floor because it was very slippery. But all in all a wonderful stay!"
The price is NZ$346
includes taxes & fees
6 Jun - 7 Jun
Piper's Place - 2 Bedroom House in DT Hamilton
The Mary Lou - Entire 2 Bedroom Apt in Quilt Town, USA
9.6 out of 10, Exceptional, (26)
"Excellent!!"
The price is NZ$291
includes taxes & fees
6 Jun - 7 Jun
The Mary Lou - Entire 2 Bedroom Apt in Quilt Town, USA
The Carolyn - Entire 2 Bedroom Apt in Quilt Town, USA
9.8 out of 10, Exceptional, (10)
"We had a lovely time. The condo was perfect for three ladies. First floor was best. Thank you."
The price is NZ$305
includes taxes & fees
15 Jun - 16 Jun
The Carolyn - Entire 2 Bedroom Apt in Quilt Town, USA
Cameron Nature Retreat: Hike, Bike & More!
3.5 star property
Cameron Nature Retreat: Hike, Bike & More!
The Delores - Entire 2 Bedroom Apt in Quilt Town, USA
9.8 out of 10, Exceptional, (33)
"We weren't able to access the original property we rented. After multiple attempts by myself and the property manager, we were moved to another property. This review is for the place we stayed. We were very comfortable and would recommend it."
The price is NZ$326
includes taxes & fees
6 Jun - 7 Jun
The Delores - Entire 2 Bedroom Apt in Quilt Town, USA
The Bernice - Entire 2 Bedroom Apt in Quilt Town, USA
9.6 out of 10, Exceptional, (14)
"Great location and was clean and comfortable."
The price is NZ$330
includes taxes & fees
9 Jun - 10 Jun
The Bernice - Entire 2 Bedroom Apt in Quilt Town, USA
8th Street Haven - House in DT Hamilton
9.6 out of 10, Exceptional, (9)
"Good option for 4-5 quilters. It’s a cute and comfortable stay."
8th Street Haven - House in DT Hamilton
Rose - Apartment suite in Quilt Town!
10.0 out of 10, Exceptional, (6)
"Great stay"
The price is NZ$300
includes taxes & fees
9 Jun - 10 Jun
Rose - Apartment suite in Quilt Town!
Don't see what you're looking for?
See all available properties in Winston
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.

Other types of properties in Winston you may be interested in

Red Roof Inn Cameron
2.0 star property
8.8 out of 10, Excellent, (1003)
"Working on road in front of property,..a little dusty but the area seemed safe and quiet"
The price is NZ$139
includes taxes & fees
30 Jun - 1 Jul
Red Roof Inn Cameron
SureStay Hotel by Best Western Cameron
2.5 star property
8.4 out of 10, Very good, (969)
"Perfect for what we needed!"
The price is NZ$123
includes taxes & fees
12 Jun - 13 Jun
SureStay Hotel by Best Western Cameron
Days Inn by Wyndham Cameron
2.0 star property
7.8 out of 10, Good, (673)
"location, price"
The price is NZ$126
includes taxes & fees
23 Jun - 24 Jun
Days Inn by Wyndham Cameron
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.

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 Winston 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 Winston. 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 Winston. Seeing all the best attractions is bound to make you fall in love with Winston. 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 Winston short-term rentals, that won’t be hard to do.

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?

Relaxing spacious home in Quilt Town USA: This holiday home rental outside of Winston is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

What can I see and do in Winston?

While you're exploring the area, Wallace State Park and Dockery Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Adam-ondi-Ahman and Daviess County Courthouse.

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.

Recent reviews of Winston properties
Expedia verified reviews