Title: Winchester Vacation Rentals from $181: Search Short-Term Rentals | Expedia.com

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![MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings](https://images.trvl-media.com/place/6056879/31f89911-167f-41d8-88d6-62f9fb8763d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6056879/31f89911-167f-41d8-88d6-62f9fb8763d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=183815&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=183815&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=183815&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=183815&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

![Property grounds](https://images.trvl-media.com/lodging/89000000/88520000/88513400/88513333/577eb255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/89000000/88520000/88513400/88513333/a137c6a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88520000/88513400/88513333/955a42e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88520000/88513400/88513333/54a2fb11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Glamping Cabin | Huge Window | Over a Creek

[](https://www.expedia.com/Glamping-Cabin-Creek-View.h88513333.Hotel-Information)

Green Township

9.8/10

Exceptional

(8 reviews)

"Loved watching the storm through the big window and listening to the rain on the roof. "

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

Crystal A.

$114 nightly

$114 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Glamping-Cabin-Creek-View.h88513333.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102370000/102364300/102364247/88c47787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102370000/102364300/102364247/dc82db30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102370000/102364300/102364247/71bf2a83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102370000/102364300/102364247/104d5e0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Glamping Cabin | Huge Window | Cliff and Animal Views

[](https://www.expedia.com/Glamping-Cabin-Huge-Window-Cliff-And-Animal-Views.h102364247.Hotel-Information)

Green Township

10/10

Exceptional

(2 reviews)

"We had a great stay, we loved the horse and goats. It was peaceful and beautiful, exactly what we needed! Will definitely stay again! "

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

Callie J.

$114 nightly

$114 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Glamping-Cabin-Huge-Window-Cliff-And-Animal-Views.h102364247.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120490000/120485600/120485520/35891546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120490000/120485600/120485520/d49d38c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120490000/120485600/120485520/ffcaf553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120490000/120485600/120485520/9898241f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleeps 4| Private Bathroom | Stunning Views

[](https://www.expedia.com/Rome-Hotels-Sleeps-4-Private-Bathroom-Stunning-Views.h120485520.Hotel-Information)

Green Township

7.0/10

Good

(4 reviews)

"We enjoyed staying at this unique cabin. Our children liked the animals and enjoyed petting some of them. "

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

Al G.

$155 nightly

$155 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Rome-Hotels-Sleeps-4-Private-Bathroom-Stunning-Views.h120485520.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/89000000/88940000/88931300/88931299/787d3232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88940000/88931300/88931299/w1024h663x0y9-cbcc3a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Books](https://images.trvl-media.com/lodging/89000000/88940000/88931300/88931299/w1015h677x5y0-0f1bffcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88940000/88931300/88931299/w1011h681x7y0-17aa4bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded in Amish Country and peaceful

[](https://www.expedia.com/Peebles-Hotels-Secluded-In-Amish-Country-And-Peaceful.h88931299.Hotel-Information)

Peebles

9.8/10

Exceptional

(28 reviews)

"Nice quite place to stay."

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

Gregory H.

$183 nightly

$183 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Peebles-Hotels-Secluded-In-Amish-Country-And-Peaceful.h88931299.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76020000/76018600/76018506/7688dddd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76020000/76018600/76018506/7d092c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76020000/76018600/76018506/48e1f2d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76020000/76018600/76018506/bc458322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Glamping Cabin | Huge Window | Tree House Feel

[](https://www.expedia.com/Glamping-Cabin-Huge-Window-Tree-House-Feel.h76018506.Hotel-Information)

Green Township

9.0/10

Wonderful

(19 reviews)

"The perfect place to connect with nature and enjoy a beautiful landscape the attention was great the beautiful place the super comfortable cabin I would come back again"

![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg)

Víctor Manuel

$114 nightly

$114 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Glamping-Cabin-Huge-Window-Tree-House-Feel.h76018506.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/112000000/111010000/111005600/111005555/181bf8a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111010000/111005600/111005555/04d9fe4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111010000/111005600/111005555/83b3c5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, toilet paper](https://images.trvl-media.com/lodging/112000000/111010000/111005600/111005555/23f5ab1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Angler

[](https://www.expedia.com/Hillsboro-Hotels-The-Angler.h111005555.Hotel-Information)

Hillsboro

8.4/10

Very Good

(10 reviews)

"Clean and great for a couple of fisherman enjoying the lake and surrounding area. "

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

Jerry P.

$170 nightly

$181 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Hillsboro-Hotels-The-Angler.h111005555.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/112000000/111010000/111005800/111005709/0cc3e53d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/112000000/111010000/111005800/111005709/9af5d8ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/112000000/111010000/111005800/111005709/9d85c284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111010000/111005800/111005709/224fdaa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The White Stag 

[](https://www.expedia.com/Hillsboro-Hotels-The-White-Stag.h111005709.Hotel-Information)

Hillsboro

7.6/10

Good

(9 reviews)

"We CD enjoyed our stay. It was spacious and cozy. The large bed is very tall so take a step stool. Mattresess are very confy. "

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

Danelia

$155 nightly

$165 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Hillsboro-Hotels-The-White-Stag.h111005709.Hotel-Information)

![Fridge, microwave, oven](https://images.trvl-media.com/lodging/94000000/93230000/93220800/93220705/b07c0f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/94000000/93230000/93220800/93220705/45f80f00_edited_4f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93230000/93220800/93220705/d767802c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Towels, toilet paper](https://images.trvl-media.com/lodging/94000000/93230000/93220800/93220705/ebb06444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country Cabin in Amish Country

[](https://www.expedia.com/Peebles-Hotels-Country-Cabin-In-Amish-Country.h93220705.Hotel-Information)

Peebles

9.8/10

Exceptional

(13 reviews)

"Beautiful clean place "

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

Casey J.

$183 nightly

$189 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Peebles-Hotels-Country-Cabin-In-Amish-Country.h93220705.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/84000000/83650000/83645500/83645402/fcc2942a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83650000/83645500/83645402/948f4769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83650000/83645500/83645402/3fc39624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83650000/83645500/83645402/a0aaf0c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cowboy Saloon Cabin

[](https://www.expedia.com/Hamersville-Hotels-Cowboy-Saloon-Cabin.h83645402.Hotel-Information)

Hamersville

9.4/10

Exceptional

(20 reviews)

"Clean & cool little place."

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

Stephen

$198 nightly

$206 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Hamersville-Hotels-Cowboy-Saloon-Cabin.h83645402.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/62000000/61500000/61498400/61498334/b90648f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/62000000/61500000/61498400/61498334/ed9ac30b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/62000000/61500000/61498400/61498334/3eeed690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/62000000/61500000/61498400/61498334/0e6ffacb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village

[](https://www.expedia.com/Hamersville-Hotels-Big-Mikes-Cabin-Located-On-The-Lake.h61498334.Hotel-Information)

Hamersville

9.6/10

Exceptional

(23 reviews)

"This was a great stay. The property owners were fabulous. Definitely coming back ."

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

Atonenent R.

$187 nightly

$195 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Hamersville-Hotels-Big-Mikes-Cabin-Located-On-The-Lake.h61498334.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116090000/116089600/116089592/bc1ad9c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/117000000/116090000/116089600/116089592/5cb126b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116090000/116089600/116089592/c283c26a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116090000/116089600/116089592/d46c5797.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bear Necessities Cabin - What Else Do You Need?

[](https://www.expedia.com/West-Union-Hotels-Bear-Necessities-Cabin-What-Else-Do-You-Need.h116089592.Hotel-Information)

West Union

9.8/10

Exceptional

(10 reviews)

"Very clean cabin and very cozy!"

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

Debbie F.

$157 nightly

$164 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/West-Union-Hotels-Bear-Necessities-Cabin-What-Else-Do-You-Need.h116089592.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105570000/105562300/105562236/fbed2d1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105570000/105562300/105562236/c17f9b0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105570000/105562300/105562236/97a04d83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105570000/105562300/105562236/70c019d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful cabin with spectacular river and scenic views.

[](https://www.expedia.com/Aberdeen-Hotels-Peaceful-Cabin-With-Spectacular-River-And-Scenic-Views-Along-With-Great-Sunsets.h105562236.Hotel-Information)

Adams County

9.8/10

Exceptional

(29 reviews)

"Great location. "

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

John S.

$348 nightly

$363 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Aberdeen-Hotels-Peaceful-Cabin-With-Spectacular-River-And-Scenic-Views-Along-With-Great-Sunsets.h105562236.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76200000/76191800/76191733/97b3decc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76200000/76191800/76191733/1b4576de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76200000/76191800/76191733/547f6d6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, bed sheets](https://images.trvl-media.com/lodging/77000000/76200000/76191800/76191733/b97fc46e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Griffis Game Hunting and/or Getaway

[](https://www.expedia.com/West-Union-Hotels-Griffis-Game-Hunting-And-Getaway.h76191733.Hotel-Information)

West Union

9.8/10

Exceptional

(31 reviews)

"Super nice host, very clean cabin."

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

BRAD T.

$212 nightly

$222 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/West-Union-Hotels-Griffis-Game-Hunting-And-Getaway.h76191733.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/74000000/73760000/73757800/73757777/a7615c91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73760000/73757800/73757777/13a54586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/74000000/73760000/73757800/73757777/9d3121d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73760000/73757800/73757777/63a51c07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tom & Jerri's Rustic Cabin located on the lake

[](https://www.expedia.com/Hamersville-Hotels-Tom-Jerris-Rustic-Cabin-Located-On-The-Lake.h73757777.Hotel-Information)

Hamersville

10/10

Exceptional

(13 reviews)

"Very cute cabin on the lake! Great stay while at the ball fields! "

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

Malia P.

$221 nightly

$230 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Hamersville-Hotels-Tom-Jerris-Rustic-Cabin-Located-On-The-Lake.h73757777.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/be61c022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/3341f262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/41e4e82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/4bdb025d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Meadowview Guest House

[](https://www.expedia.com/Hillsboro-Hotels-Meadowview-Guest-House.h90764643.Hotel-Information)

Hillsboro

10/10

Exceptional

(22 reviews)

"Amazing place to stay! Cozy, quiet, everything needed for a relaxing overnight stay! This trip was for a quick work things, but we’ll definitely be finding the time to come back to relax and take in the sights! Will definitely plan to stay here again! "

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

Stephen W.

$192 nightly

$192 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Hillsboro-Hotels-Meadowview-Guest-House.h90764643.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76020000/76018500/76018463/fe3b834d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76020000/76018500/76018463/9b6f39aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76020000/76018500/76018463/ff3738c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/77000000/76020000/76018500/76018463/9c71b124.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleeps 12| Private Bathroom | Stunning Views

[](https://www.expedia.com/Rome-Hotels-Sleeps-12-Huge-Windows-Stunning-Views.h76018463.Hotel-Information)

Blue Creek

10/10

Exceptional

(7 reviews)

"This cabin was exactly what we were looking for: Cozy, peaceful, clean, comfortable and all the amenities. Located near several great hiking spots within a short drive. Great indoor and outdoor space. Host was very friendly and responsive. Highly recommend this place!"

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

Amy H.

$315 nightly

$315 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Rome-Hotels-Sleeps-12-Huge-Windows-Stunning-Views.h76018463.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/103000000/102370000/102364300/102364251/f375f6ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102370000/102364300/102364251/d9900928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102370000/102364300/102364251/d10b9578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102370000/102364300/102364251/992b0005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Glamping Cabin | Huge Window | Valley and Cliff Views

[](https://www.expedia.com/Glamping-Cabin-Huge-Window-Valley-And-Cliff-Views.h102364251.Hotel-Information)

Green Township

10/10

Exceptional

(2 reviews)

"Property owners were very welcoming. The tree house and property were well maintained. "

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

Marci

$114 nightly

$114 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Glamping-Cabin-Huge-Window-Valley-And-Cliff-Views.h102364251.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/122000000/121730000/121729200/121729133/0111e2dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121730000/121729200/121729133/c878669f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121730000/121729200/121729133/f1697927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121730000/121729200/121729133/adfbcca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Retreat: Walk to Distillery & River

[](https://www.expedia.com/Augusta-Hotels-Charming-Retreat-Walk-To-Distillery-River.h121729133.Hotel-Information)

Augusta

10/10

Exceptional

(2 reviews)

"This space is as clean and well done as any we’ve ever stayed in! We love Augusta. You will too!"

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

Anthony A.

$168 nightly

$180 total

Apr 3 - Apr 4

Total with taxes and fees

[](https://www.expedia.com/Augusta-Hotels-Charming-Retreat-Walk-To-Distillery-River.h121729133.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/102000000/101390000/101384900/101384896/3e720f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101390000/101384900/101384896/72cc0e3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/102000000/101390000/101384900/101384896/25314d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/102000000/101390000/101384900/101384896/2983bc13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Perfect Tiny Home Getaway!

[](https://www.expedia.com/Sardinia-Hotels-Perfect-Tiny-Home-Getaway.h101384896.Hotel-Information)

Sardinia

6.0/10

(1 review)

"I really never received any information really about checking in or out. Received email with code to door. Got there had no water at bathroom sink told host said probably clogged pipe never offered to come look. Messaged at 9 am about checking out n still haven’t heard back"

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

Susan A.

$159 nightly

$172 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Sardinia-Hotels-Perfect-Tiny-Home-Getaway.h101384896.Hotel-Information)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122420000/122411700/122411630/a28bc54a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122420000/122411700/122411630/c9996ed9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122420000/122411700/122411630/e1b5ebe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/123000000/122420000/122411700/122411630/600fafd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Huntsmen

[](https://www.expedia.com/Hillsboro-Hotels-The-Huntsmen.h122411630.Hotel-Information)

Hillsboro

5.4/10

(3 reviews)

"Very clean, not super easy to understand check in instructions "

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

Jacob U.

$109 nightly

$115 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Hillsboro-Hotels-The-Huntsmen.h122411630.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=183815&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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Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Ohio%2C+United+States+of+America&regionId=183815&latLong=38.941734%2C-83.650757&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Ohio%2C+United+States+of+America&regionId=183815&latLong=38.941734%2C-83.650757&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=APARTMENT)

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## Top Winchester Hotel Reviews

![Paragon Inn Hillsboro](https://images.trvl-media.com/lodging/3000000/2980000/2974700/2974636/cc123f7e_y.jpg)

### Paragon Inn Hillsboro

10/10 Excellent

"Great friendly staff. Close to uptown Hillsboro. Clean rooms! "

[](https://expedia.com/Hillsboro-Hotels-Paragon-Inn-Hillsboro.h2974636.Hotel-Information)

![Days Inn by Wyndham Maysville Kentucky](https://images.trvl-media.com/lodging/1000000/30000/25500/25466/eec37f34_y.jpg)

### Days Inn by Wyndham Maysville Kentucky

8/10 Good

"It was ok for the money. Better that the other pet friendly hotel. "

[](https://expedia.com/Maysville-Hotels-Days-Inn-By-Wyndham-Maysville-Kentucky.h25466.Hotel-Information)

![Brown's Motel Aberdeen](https://images.trvl-media.com/lodging/11000000/10260000/10253500/10253418/a7713e3e_y.jpg)

### Brown's Motel Aberdeen

6/10 Okay

"Bathroom was way to small legs were under the sing while sitting on toilet"

[](https://expedia.com/Hillsboro-Hotels-Browns-Motel-Aberdeen.h10253418.Hotel-Information)

![Super 8 by Wyndham Maysville KY](https://images.trvl-media.com/lodging/1000000/50000/49900/49881/e877f7ea_y.jpg)

### Super 8 by Wyndham Maysville KY

8/10 Good

"Nice"

[](https://expedia.com/Maysville-Hotels-Super-8-By-Wyndham-Maysville-KY.h49881.Hotel-Information)

![Beverly hills inn](https://images.trvl-media.com/lodging/109000000/108730000/108721700/108721615/w712h1265x0y12-ec403e11_y.jpg)

### Beverly hills inn

10/10 Excellent

"Nice place to have a quiet get away with friendly service and great food at the restaurant that’s at the facility! "

[](https://expedia.com/Aberdeen-Hotels-Beverly-Hills-Inn.h108721615.Hotel-Information)

![Country Charm Cabin ](https://images.trvl-media.com/lodging/67000000/66840000/66839300/66839251/03f01970_y.jpg)

### Country Charm Cabin 

10/10 Excellent

"Good getaway. The host was very nice and we loved the hot tub. Will stay again! "

[](https://expedia.com/Hillsboro-Hotels-Country-Charm-Cabin.h66839251.Hotel-Information)

![French Quarter Inn](https://images.trvl-media.com/lodging/16000000/15590000/15589500/15589406/3a92440f_y.jpg)

### French Quarter Inn

10/10 Excellent

"Much older hotel overlooking the Ohio River in need of remodeling- this is the ONLY complaint. Front desk above and beyond helpful during a snow storm. Will stay again. "

[](https://expedia.com/Maysville-Hotels-French-Quarter-Inn.h15589406.Hotel-Information)

![Cozy private getaway built for couples to reconnect !! ](https://images.trvl-media.com/lodging/100000000/99850000/99846400/99846345/cb387f57_y.jpg)

### Cozy private getaway built for couples to reconnect !! 

8/10 Good

"The cabin was cozy. My son and I enjoyed our time there. It was not the original place I meant to book for my birthday but it was nice "

[](https://expedia.com/West-Union-Hotels-Cozy-Private-Getaway-Built-For-Couples-To-Reconnect.h99846345.Hotel-Information)

![Quality Inn Maysville](https://images.trvl-media.com/lodging/1000000/20000/17100/17042/8f60399e_y.jpg)

### Quality Inn Maysville

8/10 Good

"Just what I needed. Easy in and out and convenient for what I was doing."

[](https://expedia.com/Maysville-Hotels-Quality-Inn-Maysville-Area.h17042.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 $181 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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- [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals)
- [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals)
- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
- [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals)
- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Cabin Rentals in Winchester ](https://expedia.com/Winchester-Cabins.d183815-aaCabins.Travel-Guide-Accommodation)
- [Vacation Homes in Winchester ](https://expedia.com/Winchester-Private-Vacation-Homes.d183815-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.com/Winchester-Apartments.d183815-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.com/Winchester-Cottages.d183815-aaCottages.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.com/Winchester-Motels.d183815-aaMotels.Travel-Guide-Accommodation)
- [Farmstay in Winchester ](https://expedia.com/Winchester-Agritourism.d183815-aaAgritourism.Travel-Guide-Accommodation)
- [Guest Houses in Winchester ](https://expedia.com/Winchester-Guest-Houses.d183815-aaGuestHouses.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Winchester?

### What are some of the best vacation rentals that Winchester has to offer?

### What’s there to see and do in Winchester?

### What’s a vacation rental in Winchester like?

### Expedia's Latest Trends

Hotels

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Flights

- [Flights to Akron](https://expedia.com/Cheap-Flights-To-Akron.d602973.Travel-Guide-Flights)
- [Flights to Sandusky](https://expedia.com/Cheap-Flights-To-Sandusky.d6034855.Travel-Guide-Flights)
- [Flights to Dayton](https://expedia.com/Cheap-Flights-To-Dayton.d602974.Travel-Guide-Flights)

Cars

- [Car rentals in Akron](https://expedia.com/Car-Rentals-In-Akron.d602973.Car-Rental-Guide)
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Activities

- [Things to do in Dayton](https://expedia.com/Things-To-Do-In-Dayton.d602974.Travel-Guide-Activities)
- [Things to do in Akron](https://expedia.com/Things-To-Do-In-Akron.d602973.Travel-Guide-Activities)

General

- [Visit Put-in-Bay](https://expedia.com/Put-In-Bay.dx183802)

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