Title: Winchester Vacation Rentals from $134: Search Short-Term Rentals | Expedia.com

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=553248634983495009&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=553248634983495009&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 three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=553248634983495009&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)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=553248634983495009&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester vacation rentals

![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472100/126472041/78552352.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472100/126472041/281b2e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472100/126472041/c717ca95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472100/126472041/24e9047d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in The Gate

[](https://www.expedia.com/St-Louis-Hotels-3323-Uptown-Elegant-Escape-By-JZ-Vacation-Rentals.h126472041.Hotel-Information)

$738 nightly

$863 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/St-Louis-Hotels-3323-Uptown-Elegant-Escape-By-JZ-Vacation-Rentals.h126472041.Hotel-Information)

![House, Multiple Beds, Kitchen, City View (508 Trudy Ln) | 3 bedrooms, individually decorated, individually furnished, bed sheets](https://images.trvl-media.com/lodging/111000000/110610000/110604500/110604459/8aff9010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Multiple Beds, Kitchen, City View (508 Trudy Ln) | 3 bedrooms, individually decorated, individually furnished, bed sheets](https://images.trvl-media.com/lodging/111000000/110610000/110604500/110604459/0338a277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Multiple Beds, Kitchen, City View (508 Trudy Ln) | Game room](https://images.trvl-media.com/lodging/111000000/110610000/110604500/110604459/5ca43ed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Multiple Beds, Kitchen, City View (508 Trudy Ln) | Private kitchen | Coffee/tea maker](https://images.trvl-media.com/lodging/111000000/110610000/110604500/110604459/3d292cf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in O'Fallon

[](https://www.expedia.com/St-Louis-Hotels-The-Secret-Sojourn-JZ-Vacation-Rentals.h110604459.Hotel-Information)

$468 nightly

$552 total

Mar 18 - Mar 19

Total with taxes and fees

[](https://www.expedia.com/St-Louis-Hotels-The-Secret-Sojourn-JZ-Vacation-Rentals.h110604459.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/84000000/83130000/83121100/83121050/f3c125ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/84000000/83130000/83121100/83121050/0bbeb61f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Apartment | Living area | 42-inch Smart TV with digital channels, TV, Netflix](https://images.trvl-media.com/lodging/84000000/83130000/83121100/83121050/4a627d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment | Interior entrance](https://images.trvl-media.com/lodging/84000000/83130000/83121100/83121050/55f5dbb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Grand Center

[](https://www.expedia.com/St-Louis-Hotels-Grand-Center-Apartments.h83121050.Hotel-Information)

8.4/10

Very Good

(128 reviews)

"Very clean and very friendly people "

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

Mary

$119 nightly

$134 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/St-Louis-Hotels-Grand-Center-Apartments.h83121050.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122500/125122473/ba472020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122500/125122473/3980b4ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/126000000/125130000/125122500/125122473/f21ecd44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122500/125122473/f66eadab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in O'Fallon

[](https://www.expedia.com/St-Louis-Hotels-508-The-Secret-Sojourn-By-JZ-Vacation-Rentals.h125122473.Hotel-Information)

$489 nightly

$576 total

Mar 18 - Mar 19

Total with taxes and fees

[](https://www.expedia.com/St-Louis-Hotels-508-The-Secret-Sojourn-By-JZ-Vacation-Rentals.h125122473.Hotel-Information)

![House, Multiple Beds, Patio, City View ((#19) 3323 Vista Ave) | Private kitchen](https://images.trvl-media.com/lodging/105000000/104010000/104008500/104008447/209d3104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Multiple Beds, Patio, City View ((#19) 3323 Vista Ave) | 5 bedrooms, individually decorated, individually furnished, bed sheets](https://images.trvl-media.com/lodging/105000000/104010000/104008500/104008447/aa1a146c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Multiple Beds, Patio, City View ((#19) 3323 Vista Ave) | Living area](https://images.trvl-media.com/lodging/105000000/104010000/104008500/104008447/80ab1b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Multiple Beds, Patio, City View ((#19) 3323 Vista Ave) | Living area](https://images.trvl-media.com/lodging/105000000/104010000/104008500/104008447/f9583e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in The Gate

[](https://www.expedia.com/St-Louis-Hotels-Spacious-Family-Retreat-1-OF-2-JZ-Vacation-Rentals.h104008447.Hotel-Information)

$708 nightly

$828 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/St-Louis-Hotels-Spacious-Family-Retreat-1-OF-2-JZ-Vacation-Rentals.h104008447.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=2026-03-20&endDate=2026-03-21&regionId=553248634983495009&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Missouri%2C+United+States+of+America&regionId=553248634983495009&latLong=38.590331%2C-90.5279&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=CABIN)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Missouri%2C+United+States+of+America&regionId=553248634983495009&latLong=38.590331%2C-90.5279&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=VILLA)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Missouri%2C+United+States+of+America&regionId=553248634983495009&latLong=38.590331%2C-90.5279&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=APART_HOTEL)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Missouri%2C+United+States+of+America&regionId=553248634983495009&latLong=38.590331%2C-90.5279&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Missouri%2C+United+States+of+America&regionId=553248634983495009&latLong=38.590331%2C-90.5279&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Missouri%2C+United+States+of+America&regionId=553248634983495009&latLong=38.590331%2C-90.5279&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Missouri%2C+United+States+of+America&regionId=553248634983495009&latLong=38.590331%2C-90.5279&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=CONDO)

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## Top Winchester Hotel Reviews

![Drury Plaza Hotel St. Louis at the Arch](https://images.trvl-media.com/lodging/1000000/550000/546300/546271/78b2a688_y.jpg)

### Drury Plaza Hotel St. Louis at the Arch

10/10 Excellent

"All the staff were super friendly and helpful!!"

[](https://expedia.com/St-Louis-Hotels-Drury-Plaza-Hotel-St-Louis-At-The-Arch.h546271.Hotel-Information)

![Home2 Suites by Hilton St. Louis Downtown](https://images.trvl-media.com/lodging/77000000/76520000/76510800/76510729/104b5741_y.jpg)

### Home2 Suites by Hilton St. Louis Downtown

10/10 Excellent

"Very good"

[](https://expedia.com/St-Louis-Hotels-Home2-Suites-St-Louis-Downtown.h76510729.Hotel-Information)

![Drury Inn & Suites St. Louis Union Station](https://images.trvl-media.com/lodging/1000000/40000/37700/37651/151222b4_y.jpg)

### Drury Inn & Suites St. Louis Union Station

10/10 Excellent

"Breakfast was amazing and offered so many choices. Room was clean and facilities were really well kept. But the best part of the whole trip was the staff. So friendly and welcoming, we will definitely be back"

[](https://expedia.com/St-Louis-Hotels-Drury-Inn-St-Louis-At-Union-Station.h37651.Hotel-Information)

![Magnolia Hotel St. Louis, a Tribute Portfolio Hotel](https://images.trvl-media.com/lodging/9000000/8140000/8132000/8131949/4b87c2a3_y.jpg)

### Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

10/10 Excellent

"Super clean"

[](https://expedia.com/St-Louis-Hotels-Magnolia-Hotel-St-Louis.h8131949.Hotel-Information)

![Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham](https://images.trvl-media.com/lodging/1000000/50000/42200/42122/bfca870c_y.jpg)

### Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

6/10 Okay

"Very poor water pressure in the shower, sink didn’t drain nicely, and hotel is dated. "

[](https://expedia.com/St-Louis-Hotels-Drury-Inn-Suites-St-Louis-Fenton.h42122.Hotel-Information)

![Live by Loews - St.Louis](https://images.trvl-media.com/lodging/40000000/39170000/39161300/39161277/4c39e93f_y.jpg)

### Live by Loews - St.Louis

10/10 Excellent

"Excellent mattress, bedroom, lobby and bar! Breakfast was so good as well. This is by far our most favorite hotel!"

[](https://expedia.com/St-Louis-Hotels-Live-By-Lowes-StLouis.h39161277.Hotel-Information)

![Marriott St. Louis Grand](https://images.trvl-media.com/lodging/1000000/910000/904800/904712/4c313173_y.jpg)

### Marriott St. Louis Grand

10/10 Excellent

"Overall quality hotel. "

[](https://expedia.com/St-Louis-Hotels-Marriott-St-Louis-Grand.h904712.Hotel-Information)

![Pear Tree Inn St. Louis Near Union Station](https://images.trvl-media.com/lodging/1000000/30000/26600/26572/0bb9dbf3_y.jpg)

### Pear Tree Inn St. Louis Near Union Station

10/10 Excellent

"Staff was very friendly and we felt like the room was nice and clean. The continental breakfast was good with plenty of variety. "

[](https://expedia.com/St-Louis-Hotels-Pear-Tree-Inn-St-Louis-Near-Union-Station.h26572.Hotel-Information)

![Hyatt Regency St. Louis at The Arch](https://images.trvl-media.com/lodging/1000000/20000/14900/14877/335a172e_y.jpg)

### Hyatt Regency St. Louis at The Arch

10/10 Excellent

"Perfect location if you want to spend time touring the Gateway Park. "

[](https://expedia.com/St-Louis-Hotels-Hyatt-Regency-St-Louis-At-The-Arch.h14877.Hotel-Information)

## Find out more about Winchester

**Everything you need to know about Winchester 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 Winchester 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 Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Winchester vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Winchester. 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 Winchester 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 $134 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 Winchester rentals**

At Expedia, we put the best Winchester 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 Winchester 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 Winchester 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 Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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- [Vacation Homes in Winchester ](https://expedia.com/Winchester-Private-Vacation-Homes.d553248634983495009-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.com/Winchester-Apartments.d553248634983495009-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Winchester ](https://expedia.com/Winchester-Condos.d553248634983495009-aaCondos.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.com/Winchester-Cottages.d553248634983495009-aaCottages.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.com/Winchester-Motels.d553248634983495009-aaMotels.Travel-Guide-Accommodation)
- [Aparthotels in Winchester ](https://expedia.com/Winchester-Apart-Hotels.d553248634983495009-aaApartHotels.Travel-Guide-Accommodation)
- [Villas in Winchester ](https://expedia.com/Winchester-Villas.d553248634983495009-aaVillas.Travel-Guide-Accommodation)
- [Cabin Rentals in Winchester ](https://expedia.com/Winchester-Cabins.d553248634983495009-aaCabins.Travel-Guide-Accommodation)
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- [Guest Houses in Winchester ](https://expedia.com/Winchester-Guest-Houses.d553248634983495009-aaGuestHouses.Travel-Guide-Accommodation)
- [Hostels in Winchester ](https://expedia.com/Winchester-Hostels.d553248634983495009-aaHostels.Travel-Guide-Accommodation)
- [Farmstay in Winchester ](https://expedia.com/Winchester-Agritourism.d553248634983495009-aaAgritourism.Travel-Guide-Accommodation)

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