Title: Winchester Vacation Rentals from $100: Search Short-Term Rentals | Expedia.com

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=3000435714&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=3000435714&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 three months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=3000435714&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)

In four months

[Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=3000435714&startDate=2026-07-24&endDate=2026-07-26&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

![Dining](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w906h683x60y0-f10f078b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w905h683x60y0-bbfcfe44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w525h683x260y0-46d39fba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w905h683x60y0-6bba3640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL 

[](https://www.expedia.com/Jacksonville-Hotels-Bunkhouse-Seventy-Four.h103428476.Hotel-Information)

Jacksonville

10/10

Exceptional

(17 reviews)

"Always a nice place to stay."

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

Pete D.

$119 nightly

$126 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Jacksonville-Hotels-Bunkhouse-Seventy-Four.h103428476.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/w3096h4111x0y17-1e7de191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/270-42b93eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/601e94c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/3245f16c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee

[](https://www.expedia.com/Murrayville-Hotels-Peace-On-The-Prairie-Too-Tiny-House.h33294577.Hotel-Information)

Murrayville

9.8/10

Exceptional

(63 reviews)

"We had such a great experience staying here. The property was beautiful and the hosts were very welcoming and friendly. The property was very pet friendly as well. We will definitely go back for the peace and quiet!"

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

Mandy S.

$131 nightly

$139 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Murrayville-Hotels-Peace-On-The-Prairie-Too-Tiny-House.h33294577.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/23000000/22130000/22120700/22120643/18301817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22130000/22120700/22120643/3d282ac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, Netflix, books, streaming services](https://images.trvl-media.com/lodging/23000000/22130000/22120700/22120643/80808c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/23000000/22130000/22120700/22120643/0a889b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peace on the Prairie — Quiet Nature Retreat on 24 Acres

[](https://www.expedia.com/Murrayville-Hotels-Peace-On-The-Prairie-Native-Prairie-Setting-Pets-Allowed.h22120643.Hotel-Information)

Murrayville

10/10

Exceptional

(29 reviews)

"Yes, everything was very nice"

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

Cary W.

$95 nightly

$100 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Murrayville-Hotels-Peace-On-The-Prairie-Native-Prairie-Setting-Pets-Allowed.h22120643.Hotel-Information)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/21000000/20350000/20348900/20348849/ff0589d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/21000000/20350000/20348900/20348849/cd635bd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/21000000/20350000/20348900/20348849/382a07f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/21000000/20350000/20348900/20348849/80670dd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Farmhouse Loft "Greene County's Guesthouse"

[](https://www.expedia.com/Carrollton-Hotels-The-Farmhouse-Loft-Greene-Countys-Guesthouse.h20348849.Hotel-Information)

Carrollton

9.8/10

Exceptional

(61 reviews)

"Stayed at the Farmhouse Loft for a local wedding. It met all our expectations. Great location on the town square. Will definitely stay there again "

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

Gregory D.

$155 nightly

$164 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Carrollton-Hotels-The-Farmhouse-Loft-Greene-Countys-Guesthouse.h20348849.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/9ef3ff50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/1abf71d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/3b40112f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/269b2632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

[](https://www.expedia.com/Completely-Renonvated-Country-Home-With-Llamas-Just-Outside-THE-Windows.h38750608.Hotel-Information)

Bluffs

10/10

Exceptional

(59 reviews)

"Beautiful place, highly recommend "

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

Anthony S.

$204 nightly

$216 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Completely-Renonvated-Country-Home-With-Llamas-Just-Outside-THE-Windows.h38750608.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w1021h680x0y0-e4ca8d16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w1015h683x4y0-0f291390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w1016h683x4y0-c22df824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w449h683x287y0-7464266c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville 

[](https://www.expedia.com/Jacksonville-Hotels-Audreys-Abode.h103428480.Hotel-Information)

Jacksonville

10/10

Exceptional

(11 reviews)

"The cabin is perfect for creating a relaxing atmosphere. We always like our stay there."

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

James Z.

$149 nightly

$158 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Jacksonville-Hotels-Audreys-Abode.h103428480.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120120000/120110900/120110900/bdc25008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120120000/120110900/120110900/65f0368f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120120000/120110900/120110900/fe81fa46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120120000/120110900/120110900/fc67e1b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area

[](https://www.expedia.com/Pleasant-Hill-Hotels-Charming-2-Bedroom-Barnloft-On-Hobby-Farm-In-Pleasant-Hill-Pittsfield-Area.h120110900.Hotel-Information)

Pleasant Hill

$175 nightly

$185 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Pleasant-Hill-Hotels-Charming-2-Bedroom-Barnloft-On-Hobby-Farm-In-Pleasant-Hill-Pittsfield-Area.h120110900.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119350000/119345100/119345044/588066c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119350000/119345100/119345044/08d9964c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119350000/119345100/119345044/91f1b878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119350000/119345100/119345044/9f67a79c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dave’s River House

[](https://www.expedia.com/Mozier-Hotels-Waterfront-Cottage-In-Calhoun-County.h119345044.Hotel-Information)

Mozier

$244 nightly

$258 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Mozier-Hotels-Waterfront-Cottage-In-Calhoun-County.h119345044.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/304bbf41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1080h1437x0y3-5f7123c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1079h1437x0y3-36d6779a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1079h1437x0y3-bfee123b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland 

[](https://www.expedia.com/Pittsfield-Hotels-Lakeside-Lodge-Of-LEGENDS-A-Wilderness-Wanderers-Wonderland.h109404431.Hotel-Information)

Pittsfield

$330 nightly

$350 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Pittsfield-Hotels-Lakeside-Lodge-Of-LEGENDS-A-Wilderness-Wanderers-Wonderland.h109404431.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=2026-04-14&endDate=2026-04-15&regionId=3000435714&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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Private vacation homes

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Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America&regionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=APARTMENT)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America&regionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=COTTAGE)

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## Top Winchester Hotel Reviews

![Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w1021h680x0y0-e4ca8d16_y.jpg)

### Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville 

10/10 Excellent

"Was an excellent place to stay for the weekend."

[](https://expedia.com/Jacksonville-Hotels-Audreys-Abode.h103428480.Hotel-Information)

![Jacksonville Inn & Suites](https://images.trvl-media.com/lodging/126000000/125260000/125256100/125256069/aa0e636e_y.jpg)

### Jacksonville Inn & Suites

10/10 Excellent

"Clean rooms helpful staff "

[](https://expedia.com/Jacksonville-Hotels-Jacksonville-Hotel.h125256069.Hotel-Information)

![Quality Inn Jacksonville near I-72](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b_y.jpg)

### Quality Inn Jacksonville near I-72

10/10 Excellent

"Room was easily accessible, pool was convenient and we both slept well in the comfy bed. "

[](https://expedia.com/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information)

![Sleep Inn & Suites South Jacksonville](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3_y.jpg)

### Sleep Inn & Suites South Jacksonville

10/10 Excellent

"Nice breakfast. Hotel in great condition. Great place. "

[](https://expedia.com/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information)

![Best Western Jacksonville Inn](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg)

### Best Western Jacksonville Inn

10/10 Excellent

"The lady who checked me in on the cool scrub top was amazing, I havw Tourette Syndrome which makes it very difficult for me to stay in hotels, she was super sweet and accomadative. "

[](https://expedia.com/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information)

![Holiday Inn Express Hotel & Suites Jacksonville by IHG](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f_y.jpg)

### Holiday Inn Express Hotel & Suites Jacksonville by IHG

8/10 Good

"Good place to stay, property might be a little outdated and needs updating but clean. Staff was excellent! "

[](https://expedia.com/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information)

![Monroe Street Suites](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/946d8e4a_y.jpg)

### Monroe Street Suites

10/10 Excellent

"A unique luxurious find for rest and respite on a long trip home. Would stay here again, without any hesitation!"

[](https://expedia.com/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information)

![Hampton Inn Jacksonville](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9_y.jpg)

### Hampton Inn Jacksonville

10/10 Excellent

"The staff was great. We were worried staying at a pet-friendly hotel, but the property and our room looked and smelled fresh and clean. My only complaint is that the beds were too firm for my taste. "

[](https://expedia.com/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information)

![Green Acres Hotel](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/87b66cdb_y.jpg)

### Green Acres Hotel

10/10 Excellent

"Good place to stay!"

[](https://expedia.com/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.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 $100 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.

## Explore a world of travel with Expedia

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- [Vacation Homes in Winchester ](https://expedia.com/Winchester-Private-Vacation-Homes.d3000435714-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cabin Rentals in Winchester ](https://expedia.com/Winchester-Cabins.d3000435714-aaCabins.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.com/Winchester-Cottages.d3000435714-aaCottages.Travel-Guide-Accommodation)
- [Lodges in Winchester ](https://expedia.com/Winchester-Lodges.d3000435714-aaLodges.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.com/Winchester-Apartments.d3000435714-aaApartments.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.com/Winchester-Motels.d3000435714-aaMotels.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.com/Winchester-Bed-And-Breakfast.d3000435714-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Farmstay in Winchester ](https://expedia.com/Winchester-Agritourism.d3000435714-aaAgritourism.Travel-Guide-Accommodation)

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