Winston Holiday Rentals

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Holiday Rentals in Winston

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$309
per night
16 Jun - 17 Jun
Modern Home in Gallatin
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$273
per night
15 Jun - 16 Jun
The Deannie - Entire 2 Bedroom Apt in Quilt Town, USA
Comfortable Two-Story Family Home in Picturesque Small Town USA
9.8 out of 10, Exceptional, (82)
"We had a great time! Loved the details, and the cupcakes!"
The price is NZ$463
per night
22 Jun - 23 Jun
Comfortable Two-Story Family Home in Picturesque Small Town USA
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The Gingerbread House in Quilt Town, USA!
10.0 out of 10, Exceptional, (52)
"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$580
per night
15 Jun - 16 Jun
The Gingerbread House in Quilt Town, USA!
The Irene - Entire 2 Bedroom Apt in Quilt Town, USA
9.8 out of 10, Exceptional, (20)
"It was so close to downtown, just a couple blocks down. It was a beautiful apartment very clean and updated. Would definitely stay here if we come again "
The price is NZ$273
per night
15 Jun - 16 Jun
The Irene - Entire 2 Bedroom Apt in Quilt Town, USA
Gallatin Get-Away Bungalow Perfect for quilters, hunters, or families!
10.0 out of 10, Exceptional, (1)
"Host was very generous and easy to communicate with. We had a fun time staying here and had everything we needed. Would definitely come back again!"
The price is NZ$334
per night
12 Jun - 13 Jun
Gallatin Get-Away Bungalow Perfect for quilters, hunters, or families!
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
per night
10 Jun - 11 Jun
Hamilton Getaway -Entire House in DT Hamilton
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 Betty Blue, Quilt Town, USA!
10.0 out of 10, Exceptional, (24)
"Very nice and quiet place and walkable to downtown. Loved the small town and all the quilt stores."
The price is NZ$460
per night
25 Jun - 26 Jun
The Betty Blue, Quilt Town, USA!
The Bird's Nest - 2 bedroom House
10.0 out of 10, Exceptional, (2)
"Everything you need for a comfy stay. One suggestion: towel racks in the bathroom. Would come back again!"
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
per night
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$345
per night
15 Jun - 16 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$290
per night
15 Jun - 16 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
per night
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$327
per night
16 Jun - 17 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$327
per night
16 Jun - 17 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$305
per night
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, (1008)
"Driving up the building is...plain. The man who checked me in was friendly despite it being the middle of the night. The room was great, the bed comfy & the breakfast was surprisingly good for the small place. "
The price is NZ$138
per night
16 Jun - 17 Jun
Red Roof Inn Cameron
SureStay Hotel by Best Western Cameron
2.5 star property
8.4 out of 10, Very good, (970)
"Perfect for what we needed!"
The price is NZ$122
per night
21 Jun - 22 Jun
SureStay Hotel by Best Western Cameron
Days Inn by Wyndham Cameron
2.0 star property
7.8 out of 10, Good, (674)
"location, price"
The price is NZ$126
per night
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.

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