Winston Vacation Rentals from $93: Search Short-Term Rentals

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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.

Kidder

Tamara

$145 nightly

Oct 13 - Oct 14

Total with taxes and fees

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

Gallatin

Theresa

$166 nightly

Oct 11 - Oct 12

Total with taxes and fees

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

$353 nightly

Oct 11 - Oct 12

Total with taxes and fees

A single-story building with a gabled roof, a front porch, and a garage door.

4. Hamilton Getaway -Entire House in DT Hamilton

Hamilton

Cindy O.

$236 nightly

Oct 11 - Oct 12

Total with taxes and fees

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

Hamilton

"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!"

Jeanette

$289 nightly

Oct 15 - Oct 16

Total with taxes and fees

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

Hamilton

$204 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

Hamilton

$213 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

Hamilton

Sherril K.

$361 nightly

Oct 11 - Oct 12

Total with taxes and fees

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Top Winston Hotel Reviews

SureStay Hotel by Best Western Cameron

8/10 Good

"Rooms were clean for the price. Staff was wonderful."

Quality Inn Cameron

10/10 Excellent

"The room and bathroom were very clean, The staff was friendly. The variety of the hot, tasty breakfast was excellent. Getting to the motel was easy and had convenient parking. Because the Quality Inn was close to the highway with a traffic light at the corner, the truck noise of stopping and gearing back up to go made sleeping soundly more challenging. However, we would stay here again if the need should arise."

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

10/10 Excellent

"This property was so cute inside and out! We enjoyed sunset from the front porch and sunrise from the back porch. It was comfortable and clean. I would love to stay here again!"

Quilter's retreat! 3 quilting spaces and 2 full bathrooms!

10/10 Excellent

"We love this property for our quilting getaway. The work stations are setup so convenient and the house is so clean. It has everything we need for a comfortable stay and the area is extremely quiet. Our host responds quickly with friendly replies. We're already booked again for next year and can't wait to return!"

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

10/10 Excellent

"We had a wonderful stay! The house was clean, comfortable, and had everything we needed for our overnight trip. There was plenty of room for our group, and the space was perfect for relaxing after a busy day.The location worked out great for our trip to Missouri Star Quilt Company, and we really appreciated having such a comfortable place to come back to. Check-in was easy, communication was great, and everything was just as described.We would definitely stay here again and would happily recommend it to others!"

Find out more about Winston

Everything you need to know about Winston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $93 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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Check prices for these dates

Our top choices for Winston vacation rentals

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

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

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

4. Hamilton Getaway -Entire House in DT Hamilton

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

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

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

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

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

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

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

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

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

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

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

Find vacation rentals that suit your style

Top Winston Hotel Reviews

SureStay Hotel by Best Western Cameron

Quality Inn Cameron

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

Red Roof Inn Cameron

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

Super 8 by Wyndham Cameron

Quilter's retreat! 3 quilting spaces and 2 full bathrooms!

The Garden Room at Shoal Creek B&B

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

Find out more about Winston

Frequently asked questions

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