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Winston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winston vacation rentals

A cylindrical metal structure with a door and windows, surrounded by a concrete walkway and a grassy area.

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

Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.
Kidder
10.0 out of 10, Exceptional, (59 reviews)
"This is such an unusual but very comfortable place. The setting is gorgeous. We loved our stay here! It’s quiet and private but still very close to town. Highly recommend!"
United States
Tamara
The price is ￥15,818
￥24,167 total
includes taxes & fees
Oct 13 - Oct 14
Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.
A modern kitchen with a wooden countertop, white cabinets, a black refrigerator, and a built-in microwave.

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

Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin
Gallatin
10.0 out of 10, Exceptional, (9 reviews)
"Hoping to stay again next year."
United States
Theresa
The price is ￥15,800
￥28,143 total
includes taxes & fees
Oct 9 - Oct 10
Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin
A modern kitchen with wooden cabinets, a dishwasher, an oven, and a built-in TV.

3. Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-free

Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-free
3.0 star property
Hamilton
The price is ￥33,496
￥60,584 total
includes taxes & fees
Oct 31 - Nov 1
Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-free
A single-story building with a gabled roof, a front porch, and a garage door.

4. Hamilton Getaway -Entire House in DT Hamilton

Hamilton Getaway -Entire House in DT Hamilton
Hamilton
9.8 out of 10, Exceptional, (61 reviews)
"The location was perfect for our group! We had a nice stay and the town of Hamilton was everything we hoped for and more!"
United States
Cindy O.
The price is ￥24,964
￥37,288 total
includes taxes & fees
Oct 11 - Oct 12
Hamilton Getaway -Entire House in DT Hamilton
A staircase with wooden steps and white balusters, a door with frosted glass panels, and a small table with a lamp and decorative items.

5. Comfortable Two-Story Family Home in Picturesque Small Town USA

Comfortable Two-Story Family Home in Picturesque Small Town USA
Hamilton
9.6 out of 10, Exceptional, (128 reviews)
"Check in and check out was very smooth. The home was beautifully decorated with antiques and quilts. Very, very clean and fully stocked with linens and the softest beds. A beautiful rest was had by all. We had breakfast and enjoyed our welcome treat on the front porch. Jennafer was amazing and gave us info to find a place to eat and a place to charge one of the cars. We all highly recommend staying here! It was a joyful wedding weekend and this beautiful home was the icing on the cake!"
United States
Jeanette
The price is ￥29,862
￥48,963 total
includes taxes & fees
Nov 2 - Nov 3
Comfortable Two-Story Family Home in Picturesque Small Town USA
A modern kitchen with a central island, stainless steel appliances, and a white backsplash.

6. Sewing Serenity B- New 2 BR Home in Hamilton, MO - 3 blocks to Missouri Star

Sewing Serenity B- New 2 BR Home in Hamilton, MO - 3 blocks to Missouri Star
Hamilton
10.0 out of 10, Exceptional, (5 reviews)
The price is ￥19,244
￥35,183 total
includes taxes & fees
Oct 21 - Oct 22
Sewing Serenity B- New 2 BR Home in Hamilton, MO - 3 blocks to Missouri Star
A modern kitchen with stainless steel appliances, a microwave, oven, and a coffee maker on the countertop.

7. Patchwork Paradise B - New 2BR Home 3 Blocks from Missouri Star

Patchwork Paradise B - New 2BR Home 3 Blocks from Missouri Star
Hamilton
10.0 out of 10, Exceptional, (5 reviews)
The price is ￥20,406
￥36,603 total
includes taxes & fees
Oct 25 - Oct 26
Patchwork Paradise B - New 2BR Home 3 Blocks from Missouri Star
A modern kitchen with wooden cabinets, a dishwasher, an oven, and a built-in TV.

8. Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-Free

Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-Free
Hamilton
10.0 out of 10, Exceptional, (2 reviews)
"This was the perfect house to sit and relax with friends. And it was very convenient to the downtown area of Hamilton. I will be booking this house again if available for future visits."
United States
Sherril K.
The price is ￥26,070
￥61,144 total
includes taxes & fees
Oct 11 - Oct 12
Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-Free
A modern kitchen with a central island, stainless steel appliances, and white cabinetry.

9. Sewing Serenity A - New 2BR Home in Hamilton, 3 Blocks to Missouri Star

Sewing Serenity A - New 2BR Home in Hamilton, 3 Blocks to Missouri Star
Hamilton
10.0 out of 10, Exceptional, (5 reviews)
The price is ￥18,934
￥34,860 total
includes taxes & fees
Oct 28 - Oct 29
Sewing Serenity A - New 2BR Home in Hamilton, 3 Blocks to Missouri Star
A kitchen with white cabinets, a stainless steel stove, and a window with blinds.

10. Piper's Place - 2 Bedroom House in DT Hamilton

Piper's Place - 2 Bedroom House in DT Hamilton
Hamilton
9.4 out of 10, Exceptional, (21 reviews)
"Very clean and close to Missouri Star."
United States
Lori D.
The price is ￥21,962
￥33,970 total
includes taxes & fees
Oct 9 - Oct 10
Piper's Place - 2 Bedroom House in DT Hamilton
A wooden staircase leading to a house with white siding and a visible window.

11. Spacious 1 BR Carriage House - 2 min walk to Missouri Star

Spacious 1 BR Carriage House - 2 min walk to Missouri Star
Hamilton
10.0 out of 10, Exceptional, (4 reviews)
"Very clean and nice! Close to walk to shops! Highly recommend! Will stay again"
United States
Kelly O.
The price is ￥18,581
￥32,425 total
includes taxes & fees
Oct 13 - Oct 14
Spacious 1 BR Carriage House - 2 min walk to Missouri Star
A living room with a leather sofa, patterned rug, wooden flooring, dark wooden columns, and a ceiling fan.

12. 1920s Restored Home-walk to MSQC shops, Quilt Town USA

1920s Restored Home-walk to MSQC shops, Quilt Town USA
Hamilton
10.0 out of 10, Exceptional, (21 reviews)
"Great house and the area is great."
United States
Debbi D.
The price is ￥36,127
￥68,056 total
includes taxes & fees
Oct 18 - Oct 19
1920s Restored Home-walk to MSQC shops, Quilt Town USA
A wooden door with a step leading into a building.

13. Cozy 1-bedroom cabin in peaceful Jameson with AC

Cozy 1-bedroom cabin in peaceful Jameson with AC
Jameson
The price is ￥9,954
￥15,413 total
includes taxes & fees
Oct 12 - Oct 13
Cozy 1-bedroom cabin in peaceful Jameson with AC
A modern kitchen with white cabinets, stainless steel appliances, and a wooden countertop.

14. Patchwork Paradise A - New 2BR Home - 5 Minute walk to Missouri Star

Patchwork Paradise A - New 2BR Home - 5 Minute walk to Missouri Star
Hamilton
9.8 out of 10, Exceptional, (7 reviews)
"It was very clean and had plenty of room"
United States
Sally D.
The price is ￥18,747
￥34,640 total
includes taxes & fees
Oct 25 - Oct 26
Patchwork Paradise A - New 2BR Home - 5 Minute walk to Missouri Star
Two wooden Adirondack chairs and a fire pit with logs in a grassy field.

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

Family/pet-friendly, quiet glamping getaway. Belle Tent/ Yurt out the Country.
Pattonsburg
8.8 out of 10, Excellent, (6 reviews)
"The place was not as private as we had hoped for but it was nice and relaxing away from the city. "
United States
James I.
The price is ￥10,665
￥14,542 total
includes taxes & fees
Oct 12 - Oct 13
Family/pet-friendly, quiet glamping getaway. Belle Tent/ Yurt out the Country.
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

Red Roof Inn Cameron

Red Roof Inn Cameron

8/10 Good
"Breakfast was just okay. Staff very friendly and helpful."
Karen 1-night trip
Posted 5 hours ago
Red Roof Inn Cameron

Find out more about Winston

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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?

Charming 2BR Cottage - Short walk to Missouri Star & Downtown Hamilton: Visitors like this Winston vacation home rental. It offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Winston?

While you're exploring the area, Dockery Park and Kelsey Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Cameron Veteran's Memorial Golf Club and Adam-ondi-Ahman.

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.