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Winston Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (57 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 AED 367
AED 561 total
includes taxes & fees
1 Oct - 2 Oct
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 AED 367
AED 654 total
includes taxes & fees
1 Oct - 2 Oct
Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin
A modern kitchen with a central island, stainless steel appliances, and a white backsplash.

3. 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 AED 413
AED 769 total
includes taxes & fees
21 Oct - 22 Oct
Sewing Serenity B- New 2 BR Home in Hamilton, MO - 3 blocks to Missouri Star
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 AED 580
AED 867 total
includes taxes & fees
1 Oct - 2 Oct
Hamilton Getaway -Entire House in DT Hamilton
A modern kitchen with stainless steel appliances, a microwave, oven, and a coffee maker on the countertop.

5. 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, (3 reviews)
"Very nice and clean space for a fun one night stay in Hamilton! Plan to make this trip again in the future for more crafting supplies and will absolutely plan to stay here again."
United States
Reed C.
The price is AED 401
AED 760 total
includes taxes & fees
1 Oct - 2 Oct
Patchwork Paradise B - New 2BR Home 3 Blocks from Missouri Star
A modern kitchen with white cabinetry, a central island, and a dining area with chairs and a chandelier.

6. Charming 2BR Cottage - Short walk to Missouri Star & Downtown Hamilton

Charming 2BR Cottage - Short walk to Missouri Star & Downtown Hamilton
Hamilton
9.8 out of 10, Exceptional, (7 reviews)
"Had a great stay"
United States
R F.
The price is AED 382
AED 806 total
includes taxes & fees
1 Oct - 2 Oct
Charming 2BR Cottage - Short walk to Missouri Star & Downtown Hamilton
A wooden door with a step leading into a building.

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

Cozy 1-bedroom cabin in peaceful Jameson with AC
Jameson
The price is AED 221
AED 348 total
includes taxes & fees
4 Oct - 5 Oct
Cozy 1-bedroom cabin in peaceful Jameson with AC
A modern kitchen with a central island, stainless steel appliances, and white cabinetry.

8. 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, (3 reviews)
"It was in a perfect location for us for exploring Hamilton and the surrounding towns."
United States
Anonymous traveler
The price is AED 382
AED 736 total
includes taxes & fees
1 Oct - 2 Oct
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.

9. 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)
"The house was clean , nicely updated and had everything we needed for a comfortable stay. We would definitely stay there again!!!"
United States
Mary G.
The price is AED 511
AED 790 total
includes taxes & fees
1 Oct - 2 Oct
Piper's Place - 2 Bedroom House in DT Hamilton
A wooden staircase leading to a house with white siding and a visible window.

10. 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 AED 401
AED 717 total
includes taxes & fees
1 Oct - 2 Oct
Spacious 1 BR Carriage House - 2 min walk to Missouri Star
A modern kitchen with wooden cabinets, a dishwasher, an oven, and a built-in TV.

11. 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 AED 606
AED 1,421 total
includes taxes & fees
1 Oct - 2 Oct
Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-Free
A modern kitchen with wooden cabinets, a dishwasher, an oven, and a built-in TV.

12. 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 AED 779
AED 1,408 total
includes taxes & fees
1 Oct - 2 Oct
Hamilton Charm Place, 4 Bdrm, 2 Bath, Step-free
A living room with a leather sofa, patterned rug, wooden flooring, dark wooden columns, and a ceiling fan.

13. 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 AED 840
AED 1,582 total
includes taxes & fees
4 Oct - 5 Oct
1920s Restored Home-walk to MSQC shops, Quilt Town USA
A staircase with wooden steps and white balusters, a door with frosted glass panels, and a small table with a lamp and decorative items.

14. 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, (127 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 AED 694
AED 1,138 total
includes taxes & fees
7 Oct - 8 Oct
Comfortable Two-Story Family Home in Picturesque Small Town USA
A modern kitchen with white cabinets, stainless steel appliances, and a wooden countertop.

15. 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, (6 reviews)
"It was very clean and had plenty of room"
United States
Sally D.
The price is AED 420
AED 785 total
includes taxes & fees
15 Oct - 16 Oct
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.

16. 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 AED 248
AED 338 total
includes taxes & fees
5 Oct - 6 Oct
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

10/10 Excellent
"I love how many plugs there were!"
Emily 4-night trip
Posted 2 days ago
Red Roof Inn Cameron

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.