Title: Winchester Vacation Rentals from CA $158: Short-Term Rentals for 2026 | Expedia.ca

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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)

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.ca/Hotel-Search?regionId=183815&startDate=2026-07-17&endDate=2026-07-19&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)

![Exterior](https://images.trvl-media.com/lodging/89000000/88520000/88513400/88513333/39d85310.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.ca/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.

CA $96

CA $158 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/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)

![Exterior](https://images.trvl-media.com/lodging/103000000/102370000/102364300/102364247/51cd9be1.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.ca/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.

CA $96

CA $158 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/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)

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

![TV](https://images.trvl-media.com/lodging/121000000/120490000/120485600/120485520/5ac27e0c.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.ca/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.

CA $187

CA $215 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/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.ca/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.

CA $145

CA $251 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/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)

![Exterior](https://images.trvl-media.com/lodging/77000000/76020000/76018600/76018506/48e1f2d5.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)

![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.ca/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

CA $96

CA $158 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/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)

![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)

![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)

### The Angler

[](https://www.expedia.ca/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.

CA $139

CA $176 total

includes taxes & fees

Mar 28 - Mar 29

[](https://www.expedia.ca/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)

![Towels, toilet paper](https://images.trvl-media.com/lodging/112000000/111010000/111005800/111005709/13810599.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)

![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.ca/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

CA $187

CA $228 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/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)

![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)

![Exterior detail](https://images.trvl-media.com/lodging/94000000/93230000/93220800/93220705/093e3d48_edited_f80b.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)

### Country Cabin in Amish Country

[](https://www.expedia.ca/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.

CA $145

CA $259 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/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)

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

![Exterior](https://images.trvl-media.com/lodging/84000000/83650000/83645500/83645402/abd7b430.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.ca/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

CA $187

CA $285 total

includes taxes & fees

Mar 28 - Mar 29

[](https://www.expedia.ca/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)

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

![Smart TV, table tennis, video library](https://images.trvl-media.com/lodging/62000000/61500000/61498400/61498334/da52ca39.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.ca/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.

CA $173

CA $269 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/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)

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

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116090000/116089600/116089592/18bd1ad5.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)

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

[](https://www.expedia.ca/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.

CA $122

CA $228 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/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)

![Interior](https://images.trvl-media.com/lodging/106000000/105570000/105562300/105562236/70c019d5.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)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/106000000/105570000/105562300/105562236/7bc057fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/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.

CA $264

CA $455 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/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/bd41c369.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.ca/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.

CA $187

CA $304 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/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)

![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73760000/73757800/73757777/63a51c07.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)

![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)

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

[](https://www.expedia.ca/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.

CA $215

CA $319 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/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)

![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)

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

![Interior](https://images.trvl-media.com/lodging/91000000/90770000/90764700/90764643/04625cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Meadowview Guest House

[](https://www.expedia.ca/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.

CA $150

CA $256 total

includes taxes & fees

Mar 28 - Mar 29

[](https://www.expedia.ca/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)

![TV](https://images.trvl-media.com/lodging/77000000/76020000/76018500/76018463/9c71b124.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)

### Sleeps 12| Private Bathroom | Stunning Views

[](https://www.expedia.ca/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.

CA $346

CA $434 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/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)

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

![Interior](https://images.trvl-media.com/lodging/103000000/102370000/102364300/102364251/3264b650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/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

CA $96

CA $158 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/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)

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

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/122000000/121730000/121729200/121729133/12718e35.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)

### Charming Retreat: Walk to Distillery & River

[](https://www.expedia.ca/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.

CA $151

CA $243 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/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)

![Pool](https://images.trvl-media.com/lodging/102000000/101390000/101384900/101384896/2983bc13.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)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101390000/101384900/101384896/w1860h1386x0y0-e0fa747e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Perfect Tiny Home Getaway!

[](https://www.expedia.ca/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.

CA $123

CA $239 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/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)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122420000/122411700/122411630/1e1dcf1c.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)

### The Huntsmen

[](https://www.expedia.ca/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.

CA $123

CA $160 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-04-10&endDate=2026-04-11&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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Cottages

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Private vacation homes

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Apartments

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## Top Winchester Hotel Reviews

![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.ca/Maysville-Hotels-Days-Inn-By-Wyndham-Maysville-Kentucky.h25466.Hotel-Information)

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

### Paragon Inn Hillsboro

10/10 Excellent

"Yes"

[](https://expedia.ca/Hillsboro-Hotels-Paragon-Inn-Hillsboro.h2974636.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.ca/Hillsboro-Hotels-Browns-Motel-Aberdeen.h10253418.Hotel-Information)

![The Benchmark Inn](https://images.trvl-media.com/lodging/119000000/118720000/118717500/118717477/cbdcb775_y.jpg)

### The Benchmark Inn

10/10 Excellent

"Nice resto bldg. decent price"

[](https://expedia.ca/Augusta-Hotels-The-Benchmark-Inn.h118717477.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.ca/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.ca/Aberdeen-Hotels-Beverly-Hills-Inn.h108721615.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.ca/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.ca/West-Union-Hotels-Cozy-Private-Getaway-Built-For-Couples-To-Reconnect.h99846345.Hotel-Information)

![Unique and secluded A frame home on 31 acres with hot tub.](https://images.trvl-media.com/lodging/116000000/115830000/115826300/115826209/0791da9c_y.jpg)

### Unique and secluded A frame home on 31 acres with hot tub.

10/10 Excellent

"Very nice. The view was great, and the telescope was a fun way to view it. We also really liked the coffee bar, a great treat in the mornings. Lighting up the rocks behind the house was pretty cool as well. The tv was awesome! The road in front of the house was quiet, only a few cars per day. Very nice for walking the dogs. They loved it!"

[](https://expedia.ca/Manchester-Hotels-Charming-2-Bedroom-House-With-WiFi-And-AC-In-Welcoming-Adams-County-Ohio.h115826209.Hotel-Information)

## Find out more about Winchester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winchester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Cabin Rentals in Winchester ](https://expedia.ca/Winchester-Cabins.d183815-aaCabins.Travel-Guide-Accommodation)
- [Vacation Homes in Winchester ](https://expedia.ca/Winchester-Private-Vacation-Homes.d183815-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.ca/Winchester-Apartments.d183815-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.ca/Winchester-Cottages.d183815-aaCottages.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.ca/Winchester-Motels.d183815-aaMotels.Travel-Guide-Accommodation)
- [Farmstay in Winchester ](https://expedia.ca/Winchester-Agritourism.d183815-aaAgritourism.Travel-Guide-Accommodation)
- [Lodges in Winchester ](https://expedia.ca/Winchester-Lodges.d183815-aaLodges.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.ca/Winchester-Bed-And-Breakfast.d183815-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Winchester ](https://expedia.ca/Winchester-Guest-Houses.d183815-aaGuestHouses.Travel-Guide-Accommodation)

## Frequently asked questions

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

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