Winston Vacation Rentals

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Check prices for these dates

Tonight
Jan 9 - Jan 10
Tomorrow
Jan 10 - Jan 11
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Winston vacation rentals

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

Apartment in Gallatin

Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin
10.0 out of 10, Exceptional, (6 reviews)
"Cute little home. Just right for a couple stay. Everything was clean, and smelled fresh. Cute little town, we would stay again. "
United States
Salinda W.
The price is ￥14,121
￥21,966 total
includes taxes & fees
Jan 24 - Jan 25
Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin
Fridge, microwave, oven, stovetop
The Carolyn - Entire 2 Bedroom Apt in Quilt Town, USA

Apartment in Hamilton

The Carolyn - Entire 2 Bedroom Apt in Quilt Town, USA
10.0 out of 10, Exceptional, (19 reviews)
"The apartment was perfect! Very cute. The bed was so comfortable! Loved it!! Would definitely stay there again!"
United States
Shelley S.
The price is ￥18,357
￥29,497 total
includes taxes & fees
Jan 20 - Jan 21
The Carolyn - Entire 2 Bedroom Apt in Quilt Town, USA
2 bedrooms, free WiFi, bed sheets
The Delores - Entire 2 Bedroom Apt in Quilt Town, USA

Apartment in Hamilton

The Delores - Entire 2 Bedroom Apt in Quilt Town, USA
9.8 out of 10, Exceptional, (39 reviews)
"Good location and clean for Missouri Star visitors."
United States
Judy R.
The price is ￥20,240
￥31,223 total
includes taxes & fees
Jan 11 - Jan 12
The Delores - Entire 2 Bedroom Apt in Quilt Town, USA
Fridge, microwave, oven, stovetop
The Bernice - Entire 2 Bedroom Apt in Quilt Town, USA

Apartment in Hamilton

The Bernice - Entire 2 Bedroom Apt in Quilt Town, USA
9.8 out of 10, Exceptional, (19 reviews)
"Nice place. Everything you need for a nice stay"
United States
Richard B.
The price is ￥20,240
￥31,223 total
includes taxes & fees
Jan 11 - Jan 12
The Bernice - Entire 2 Bedroom Apt in Quilt Town, USA
Interior
Comfortable Two-Story Family Home in Picturesque Small Town USA

Vacation Home in Hamilton

Comfortable Two-Story Family Home in Picturesque Small Town USA
9.8 out of 10, Exceptional, (111 reviews)
"We adored this place! So clean, so cute and so inviting! Would definitely stay there again if in the area. "
United States
EUNICE L.
The price is ￥26,689
￥42,930 total
includes taxes & fees
Jan 11 - Jan 12
Comfortable Two-Story Family Home in Picturesque Small Town USA
Interior
1920s Restored Home-walk to MSQC shops, Quilt Town USA

Vacation Home in Hamilton

1920s Restored Home-walk to MSQC shops, Quilt Town USA
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay at this perfectly renovated home! Very clean, well organized and stocked with everything you need. We highly recommend staying at this property! "
United States
Heather T.
The price is ￥37,985
￥65,913 total
includes taxes & fees
Jan 13 - Jan 14
1920s Restored Home-walk to MSQC shops, Quilt Town USA
Fridge, microwave, oven, stovetop
The Deannie - Entire 2 Bedroom Apt in Quilt Town, USA

Apartment in Hamilton

The Deannie - Entire 2 Bedroom Apt in Quilt Town, USA
9.8 out of 10, Exceptional, (63 reviews)
"Very clean, comfortable beds. Great location! Hosts were awesome. "
United States
Gwen O.
The price is ￥15,533
￥26,516 total
includes taxes & fees
Feb 1 - Feb 2
The Deannie - Entire 2 Bedroom Apt in Quilt Town, USA
Fridge, microwave, oven, stovetop
The Ingrid - Entire 2 Bedroom Apt in Quilt Town, USA

Apartment in Hamilton

The Ingrid - Entire 2 Bedroom Apt in Quilt Town, USA
9.4 out of 10, Exceptional, (27 reviews)
"Very clean...great beds...quiet neighborhood...only 2 blocks from MSQ shops"
United States
Lorrie S.
The price is ￥15,533
￥26,516 total
includes taxes & fees
Jan 16 - Jan 17
The Ingrid - Entire 2 Bedroom Apt in Quilt Town, USA
Smart TV
Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.

Cabin in Kidder

Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.
10.0 out of 10, Exceptional, (16 reviews)
"Nice , clean , quiet, place to spend the night."
United States
Kevin W.
The price is ￥15,690
￥22,751 total
includes taxes & fees
Jan 11 - Jan 12
Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.
Private kitchen
Piper's Place - 2 Bedroom House in DT Hamilton

Vacation Home in Hamilton

Piper's Place - 2 Bedroom House in DT Hamilton
9.2 out of 10, Wonderful, (13 reviews)
"House was nicely updated, conveniently located; perfect for a landing spot while we were visiting family."
United States
Margie B.
The price is ￥21,809
￥32,949 total
includes taxes & fees
Jan 11 - Jan 12
Piper's Place - 2 Bedroom House in DT Hamilton
Exterior
Hamilton Getaway -Entire House in DT Hamilton

Vacation Home in Hamilton

Hamilton Getaway -Entire House in DT Hamilton
9.8 out of 10, Exceptional, (54 reviews)
"Great stay-"
United States
IRENE H.
The price is ￥24,790
￥36,871 total
includes taxes & fees
Jan 11 - Jan 12
Hamilton Getaway -Entire House in DT Hamilton
Deluxe Apartment, 3 Bedrooms, Park View | Park view
Cameron Suites

Apartment in Cameron

Cameron Suites
3.0 star property
The price is ￥17,259
￥34,584 total
includes taxes & fees
Jan 11 - Jan 12
Cameron Suites
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

SureStay Hotel by Best Western Cameron

SureStay Hotel by Best Western Cameron

10/10 Excellent
"Excellent breakfast, parked right outside our door. "
Kirstin 1-night trip
Posted 5 days ago
SureStay Hotel by Best Western Cameron

Find out more about Winston

Search for holiday rentals in Winston on Expedia! You can easily find your home rentals, villas, holiday apartments in Winston using one of the methods below:

  • View our selection of featured holiday rentals in Winston
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  • Enter your travel dates to view the best deals on holiday rentals in Winston while they last

Look no further and take a look at our great range of rental properties in Winston!

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?

Comfortable Two-Story Family Home in Picturesque Small Town USA: Visitors like this Winston vacation home rental. It is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. 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. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Winston?

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

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.