Title: Winston Vacation Rentals from $140: Search Short-Term Rentals | Expedia.com

[Hotels in Winston](https://expedia.com/Winston-Hotels.d553248634983181173.Travel-Guide-Hotels)[Car Rentals in Winston](https://expedia.com/Car-Rentals-In-Winston.d553248634983181173.Car-Rental-Guide)[Winston Vacation Packages](https://expedia.com/Winston.d553248634983181173.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=553248634983181173&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=553248634983181173&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=553248634983181173&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=553248634983181173&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winston vacation rentals

![Smart TV](https://images.trvl-media.com/lodging/111000000/110500000/110492900/110492816/fdfcce1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110500000/110492900/110492816/1141ef7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/111000000/110500000/110492900/110492816/55d69b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110500000/110492900/110492816/eb3ed94c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Kidder-Hotels-Cozy-Cabin-With-WiFi-And-AC-In-Serene-Kidder-Come-Enjoy-This-Unique-Grainbin.h110492816.Hotel-Information)

Kidder

10/10

Exceptional

(18 reviews)

"Nice , clean , quiet, place to spend the night."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kevin W.

$145 nightly

$153 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Kidder-Hotels-Cozy-Cabin-With-WiFi-And-AC-In-Serene-Kidder-Come-Enjoy-This-Unique-Grainbin.h110492816.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/71000000/70990000/70987100/70987079/00282b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/71000000/70990000/70987100/70987079/dcd69499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/71000000/70990000/70987100/70987079/933f8648.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/71000000/70990000/70987100/70987079/da0a6c87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfortable Two-Story Family Home in Picturesque Small Town USA

[](https://www.expedia.com/Hamilton-Hotels-Comfortable-Two-Story-Family-Home-In-Picturesque-Small-Town-USA.h70987079.Hotel-Information)

Hamilton

9.6/10

Exceptional

(112 reviews)

"We adored this place! So clean, so cute and so inviting! Would definitely stay there again if in the area. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

EUNICE L.

$265 nightly

$284 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Hamilton-Hotels-Comfortable-Two-Story-Family-Home-In-Picturesque-Small-Town-USA.h70987079.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/60000000/59290000/59282600/59282599/5463533b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59290000/59282600/59282599/556b3042.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/59290000/59282600/59282599/bf5bf8a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/59290000/59282600/59282599/c9663579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hamilton Getaway -Entire House in DT Hamilton

[](https://www.expedia.com/Hamilton-Hotels-Hamilton-Getaway-Entire-House-In-DT-Hamilton.h59282599.Hotel-Information)

Hamilton

9.8/10

Exceptional

(54 reviews)

"Great stay-"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

IRENE H.

$235 nightly

$235 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Hamilton-Hotels-Hamilton-Getaway-Entire-House-In-DT-Hamilton.h59282599.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/110000000/109420000/109414700/109414671/f709f30d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109420000/109414700/109414671/1c2b1e68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109420000/109414700/109414671/ce8913ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109420000/109414700/109414671/21514177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Gallatin-Hotels-Charming-1-Bedroom-Guest-Home-With-WiFi.h109414671.Hotel-Information)

Gallatin

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Salinda W.

$140 nightly

$140 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Gallatin-Hotels-Charming-1-Bedroom-Guest-Home-With-WiFi.h109414671.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/93000000/92200000/92199100/92199006/afde3ff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92200000/92199100/92199006/7c80c013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92200000/92199100/92199006/6354e99f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathroom](https://images.trvl-media.com/lodging/93000000/92200000/92199100/92199006/4458d1a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Piper's Place - 2 Bedroom House in DT Hamilton

[](https://www.expedia.com/Hamilton-Hotels-Pipers-Place-2-Bedroom-House-In-DT-Hamilton.h92199006.Hotel-Information)

Hamilton

9.2/10

Wonderful

(13 reviews)

"House was nicely updated, conveniently located; perfect for a landing spot while we were visiting family."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Margie B.

$211 nightly

$211 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Hamilton-Hotels-Pipers-Place-2-Bedroom-House-In-DT-Hamilton.h92199006.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/114000000/113150000/113142000/113141945/w1347h1226x0y4-37fa3394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113150000/113142000/113141945/w1258h1632x0y0-5af4ae6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113150000/113142000/113141945/w1800h1698x0y4-f45e8303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113150000/113142000/113141945/c9ac2e7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Hamilton-Hotels-1920s-Restored-Home-Walk-To-MSQC-Shops.h113141945.Hotel-Information)

Hamilton

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Heather T.

$405 nightly

$434 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Hamilton-Hotels-1920s-Restored-Home-Walk-To-MSQC-Shops.h113141945.Hotel-Information)

![Deluxe Apartment, 3 Bedrooms, Park View | Park view](https://images.trvl-media.com/lodging/75000000/74710000/74704700/74704690/f105b4ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, 3 Bedrooms, Park View | In-room dining](https://images.trvl-media.com/lodging/75000000/74710000/74704700/74704690/9ed1ca1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, 3 Bedrooms, Park View | Living area | 100-inch Smart TV with digital channels, TV, Netflix](https://images.trvl-media.com/lodging/75000000/74710000/74704700/74704690/e4bcc2ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, 3 Bedrooms, Park View | 3 bedrooms, individually decorated, desk, laptop workspace](https://images.trvl-media.com/lodging/75000000/74710000/74704700/74704690/f2b04a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cameron Suites

[](https://www.expedia.com/Cameron-Hotels-Cameron-Suites.h74704690.Hotel-Information)

Cameron

$201 nightly

$220 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Cameron-Hotels-Cameron-Suites.h74704690.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/125000000/124930000/124924500/124924415/w2048h1558x0y7-91d7f57f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/125000000/124930000/124924500/124924415/58f71870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124930000/124924500/124924415/w2048h1357x0y0-29dc179f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124930000/124924500/124924415/w1080h1417x0y2-5406eb24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Porch, Walk to Missouri Star, Family Games

[](https://www.expedia.com/Hamilton-Hotels-Cozy-Porch.h124924415.Hotel-Information)

Hamilton

$186 nightly

$200 total

Feb 8 - Feb 9

Total with taxes and fees

[](https://www.expedia.com/Hamilton-Hotels-Cozy-Porch.h124924415.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/106000000/105760000/105757800/105757773/2d185477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/106000000/105760000/105757800/105757773/fece0d4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105760000/105757800/105757773/13e8dc41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/106000000/105760000/105757800/105757773/6091a449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 10 min from downtown Jamesport, MO

[](https://www.expedia.com/Jamesport-Hotels-10-Min-From-Downtown-Jamesport.h105757773.Hotel-Information)

Jamesport

2.0/10

(1 review)

"Reservation was not confirmed. We were forced to find other accommodations. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Clifton

$150 nightly

$150 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Jamesport-Hotels-10-Min-From-Downtown-Jamesport.h105757773.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-02-21&endDate=2026-02-22&regionId=553248634983181173&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

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Apartments

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Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Missouri%2C+United+States+of+America&regionId=553248634983181173&latLong=39.870004%2C-94.139947&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Missouri%2C+United+States+of+America&regionId=553248634983181173&latLong=39.870004%2C-94.139947&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

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## Top Winston Hotel Reviews

![Quality Inn Cameron](https://images.trvl-media.com/lodging/1000000/50000/42200/42192/5baaa282_y.jpg)

### Quality Inn Cameron

10/10 Excellent

"clean room. Internet wasn’t good. it kept quitting "

[](https://expedia.com/St-Joseph-Hotels-Quality-Inn-Cameron.h42192.Hotel-Information)

![Red Roof Inn Cameron](https://images.trvl-media.com/lodging/1000000/40000/40000/39991/917e85d1_y.jpg)

### Red Roof Inn Cameron

10/10 Excellent

"Very clean! Breakfast was good! Coffee was great! No complaints."

[](https://expedia.com/St-Joseph-Hotels-Red-Roof-Inn-Cameron.h39991.Hotel-Information)

![Foxy's Den cozy grain bin cabin with WiFi & AC in serene Kidder. Quiet & serene.](https://images.trvl-media.com/lodging/111000000/110500000/110492900/110492816/fdfcce1c_y.jpg)

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

10/10 Excellent

"I give them a 10 plus. This was a nice little quiet and cozy place to stay. Very clean and comfortable. I highly recommend staying here. "

[](https://expedia.com/Kidder-Hotels-Cozy-Cabin-With-WiFi-And-AC-In-Serene-Kidder-Come-Enjoy-This-Unique-Grainbin.h110492816.Hotel-Information)

![Days Inn by Wyndham Cameron](https://images.trvl-media.com/lodging/1000000/50000/42200/42165/602776a9_y.jpg)

### Days Inn by Wyndham Cameron

10/10 Excellent

"Great help"

[](https://expedia.com/St-Joseph-Hotels-Days-Inn-By-Wyndham-Cameron.h42165.Hotel-Information)

![SureStay Hotel by Best Western Cameron](https://images.trvl-media.com/lodging/1000000/20000/10500/10417/b317db33_y.jpg)

### SureStay Hotel by Best Western Cameron

10/10 Excellent

"Excellent breakfast, parked right outside our door. "

[](https://expedia.com/Cameron-Hotels-SureStay-Hotel-By-Best-Western-Cameron.h10417.Hotel-Information)

![Super 8 by Wyndham Cameron](https://images.trvl-media.com/lodging/1000000/860000/855500/855452/fbe988e4_y.jpg)

### Super 8 by Wyndham Cameron

10/10 Excellent

"We appreciated an easy stop during a long road trip."

[](https://expedia.com/St-Joseph-Hotels-Super-8-By-Wyndham-Cameron.h855452.Hotel-Information)

![Quilter's retreat! 3 quilting spaces and 2 full bathrooms!](https://images.trvl-media.com/lodging/103000000/102640000/102635200/102635133/b49dc64b_y.jpg)

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

10/10 Excellent

"Everything was great. Very nice place. Perfect for the four of us. If you're going to Hamilton I highly recommend this place."

[](https://expedia.com/Cozy-2-Bedroom-House-With-Quilting-Work-Spaces-In-The-Quilting-Town-Of-Hamilton.h102635133.Hotel-Information)

![The Farm House - Have Fun on the Farm This Fall!](https://images.trvl-media.com/lodging/107000000/106800000/106793500/106793415/e617de81_y.jpg)

### The Farm House - Have Fun on the Farm This Fall!

10/10 Excellent

"We werebin town for a quick wedding trip. This house was perfect for our group of 6 adults. The house was spacious, welcoming, clean, and accommodating. One of our party is handicapped. We had zero issues. The host was quick to respond. Our trip was definitely a 10/10\. "

[](https://expedia.com/Osborn-Hotels-The-Farm-House.h106793415.Hotel-Information)

![1920s Restored Home-walk to MSQC shops, Quilt Town USA](https://images.trvl-media.com/lodging/114000000/113150000/113142000/113141945/54e4edb9_y.jpg)

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

10/10 Excellent

"The kitchen was well stocked with essential utensils. The fridge is amazing - large, with ice maker. We enjoyed the open flow of the dining/lounge/living room area. We even had space to open a folding table to do a jigsaw puzzle. The beds are comfortable and rooms nicely decorated. Bathrooms are upstairs and down, so very convenient. We will be back! "

[](https://expedia.com/Hamilton-Hotels-1920s-Restored-Home-Walk-To-MSQC-Shops.h113141945.Hotel-Information)

## 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 $140 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.

## Explore a world of travel with Expedia

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- [Vacation Homes in Winston ](https://expedia.com/Winston-Private-Vacation-Homes.d553248634983181173-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Winston ](https://expedia.com/Winston-Apartments.d553248634983181173-aaApartments.Travel-Guide-Accommodation)
- [Farmstay in Winston ](https://expedia.com/Winston-Agritourism.d553248634983181173-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Winston ](https://expedia.com/Winston-Bed-And-Breakfast.d553248634983181173-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Motels in Winston ](https://expedia.com/Winston-Motels.d553248634983181173-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Winston ](https://expedia.com/Winston-Cabins.d553248634983181173-aaCabins.Travel-Guide-Accommodation)
- [RV Parks in Winston ](https://expedia.com/Winston-RV-Parks.d553248634983181173-aaRVParks.Travel-Guide-Accommodation)

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