Title: Winchester Vacation Rentals from CA $90: Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d177515.Travel-Guide-Hotels)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d177515.Travel-Guide-Flights)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d177515.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d177515.Destination-Travel-Guides)

![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Winchester Vacation Rentals

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Check prices for these dates

In two weeks

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=177515&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=177515&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=177515&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=177515&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)

## Our top choices for Winchester vacation rentals

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76930000/76923600/76923589/f25ef800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76930000/76923600/76923589/acfdd07e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76930000/76923600/76923589/923c16d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/77000000/76930000/76923600/76923589/c85ef593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "The Hawk Nest" cabin on Tims Ford Lake

[](https://www.expedia.ca/Winchester-Hotels-Cozy-Cabin-On-Tims-Ford-Lake-The-Hawk-Nest.h76923589.Hotel-Information)

Winchester

9.6/10

Exceptional

(18 reviews)

"Very cozy and great lake location. We definitely plan to go back."

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

Jason G.

CA $152

CA $426 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Winchester-Hotels-Cozy-Cabin-On-Tims-Ford-Lake-The-Hawk-Nest.h76923589.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103950000/103947800/103947795/8ac5ef71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103950000/103947800/103947795/5ecc67f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103950000/103947800/103947795/w2048h1362x0y3-79f38c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103950000/103947800/103947795/4290815c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tiny Home w/ RV Hookups

[](https://www.expedia.ca/Winchester-Hotels-Tiny-Home-W-RV-Hookups.h103947795.Hotel-Information)

Winchester

8.8/10

Excellent

(8 reviews)

"Very clean highly recommend if you are looking to get away and relax "

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

Jeffrey

CA $103

CA $244 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Winchester-Hotels-Tiny-Home-W-RV-Hookups.h103947795.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844265/77bb0e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844265/f9f7d354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844265/87589e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844265/70e60b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oasis on the Square

[](https://www.expedia.ca/Winchester-Hotels-Old-Town-Oasis-Charm-Convenience-On-The-Square.h103844265.Hotel-Information)

Winchester

9.8/10

Exceptional

(11 reviews)

"Great accommodations in downtown Winchester! "

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

LeBron F.

CA $112

CA $241 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Winchester-Hotels-Old-Town-Oasis-Charm-Convenience-On-The-Square.h103844265.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/109000000/108480000/108476300/108476215/89d9a169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108480000/108476300/108476215/3cab0c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/109000000/108480000/108476300/108476215/1f2a6628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/109000000/108480000/108476300/108476215/2fe9bb6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Lakeside Getaway

[](https://www.expedia.ca/Winchester-Hotels-The-Lakefront-Getaway.h108476215.Hotel-Information)

Winchester

9.6/10

Exceptional

(5 reviews)

"Incredible "

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

Jim C.

CA $28

CA $609 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Winchester-Hotels-The-Lakefront-Getaway.h108476215.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108930000/108926900/108926864/606af038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108930000/108926900/108926864/edfc7e0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/109000000/108930000/108926900/108926864/8c7452e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108930000/108926900/108926864/0e8f88cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakeview Luxe - Lake Access + Pool

[](https://www.expedia.ca/Winchester-Hotels-Lakeview-Luxe-In-Gated-Barefoot-Bay-Steps-To-Lakefront.h108926864.Hotel-Information)

Winchester

10/10

Exceptional

(3 reviews)

"Had a great stay and would recommend this property to all!"

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

Lizzie S.

CA $213

CA $837 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Winchester-Hotels-Lakeview-Luxe-In-Gated-Barefoot-Bay-Steps-To-Lakefront.h108926864.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844252/81ab0231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844252/70246f6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844252/4aa40d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844252/145aba0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Winchester's Premier Downtown Loft!

[](https://www.expedia.ca/Winchester-Hotels-Winchesters-Premier-Downtown-Loft.h103844252.Hotel-Information)

Winchester

9.8/10

Exceptional

(11 reviews)

"We thoroughly enjoyed our stay in this comfortable and beautiful apartment, right in the heart of Winchester. It’s walkable to several restaurants and a great ice cream shop. Check-in and communication were smooth. "

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

Jennifer M.

CA $120

CA $250 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Winchester-Hotels-Winchesters-Premier-Downtown-Loft.h103844252.Hotel-Information)

![Microwave, stovetop, paper towels](https://images.trvl-media.com/lodging/123000000/122340000/122331500/122331485/237e7bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122340000/122331500/122331485/edcce68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122340000/122331500/122331485/80ac04de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122340000/122331500/122331485/2d6d85e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxurious Winter Retreat/ Lynchburg, TN

[](https://www.expedia.ca/Winchester-Hotels-The-Cozy-Cruiser-Is-Awaiting-Your-Next-Adventure.h122331485.Hotel-Information)

Winchester

CA $157

CA $204 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Winchester-Hotels-The-Cozy-Cruiser-Is-Awaiting-Your-Next-Adventure.h122331485.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/119000000/118720000/118717600/118717529/0d69746e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/119000000/118720000/118717600/118717529/2b6e933d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118720000/118717600/118717529/48892147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118720000/118717600/118717529/cb694fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2-bedroom RV in awesome Winchester with WiFi, AC

[](https://www.expedia.ca/Winchester-Hotels-Cozy-2-Bedroom-RV-In-Awesome-Winchester-With-WiFi.h118717529.Hotel-Information)

Winchester

CA $136

CA $251 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Winchester-Hotels-Cozy-2-Bedroom-RV-In-Awesome-Winchester-With-WiFi.h118717529.Hotel-Information)

![5 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/111000000/110010000/110001600/110001577/d3a624b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110010000/110001600/110001577/2b56a29e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/111000000/110010000/110001600/110001577/55297514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110010000/110001600/110001577/be1f9671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxurious Lakefront Home- Marina, Boats, and Kayaks!

[](https://www.expedia.ca/Winchester-Hotels-Luxurious-Lakefront-Home-Marina.h110001577.Hotel-Information)

Winchester

10/10

Exceptional

(1 review)

"We really enjoyed our stay. The home was great! Everything you need. Love the location. Close to Winchester and the lake. Highly recommend. Already planning to stay there again."

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

Gary W.

CA $80

CA $676 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Winchester-Hotels-Luxurious-Lakefront-Home-Marina.h110001577.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91120000/91111100/91111096/0f061ff7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91120000/91111100/91111096/afc2c7f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91120000/91111100/91111096/c276f657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/92000000/91120000/91111100/91111096/78834e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gather at Tims Ford Lake

[](https://www.expedia.ca/Winchester-Hotels-Gather-At-Tims-Ford-Lake.h91111096.Hotel-Information)

Winchester

9.6/10

Exceptional

(19 reviews)

"Great house for our family. We enjoyed our week at the lake!"

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

Debra G.

CA $437

CA $1,025 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Winchester-Hotels-Gather-At-Tims-Ford-Lake.h91111096.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/108000000/107720000/107712700/107712604/e976ab22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/108000000/107720000/107712700/107712604/58c269f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107720000/107712700/107712604/bc73d15b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107720000/107712700/107712604/a37a5be9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp

[](https://www.expedia.ca/Winchester-Hotels-Lake-Lagoon.h107712604.Hotel-Information)

Winchester

10/10

Exceptional

(4 reviews)

"We were only there for 1 night but the house was clean and comfortable and perfectly suited our needs. "

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

Gwen K.

CA $413

CA $1,057 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Winchester-Hotels-Lake-Lagoon.h107712604.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/78000000/77870000/77863400/77863312/a67798e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/78000000/77870000/77863400/77863312/2d8b914d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/78000000/77870000/77863400/77863312/d35a84ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/78000000/77870000/77863400/77863312/be3c46e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family

[](https://www.expedia.ca/Winchester-Hotels-New-Close-To-Town-Lakefront-Home-Gorgeous-Water-Views-W-Dockboat-Slip.h77863312.Hotel-Information)

Winchester

10/10

Exceptional

(35 reviews)

"This was our third time staying at the property. Foresa is always so responsive and goes to great lengths to make sure our stay is great. I love the updates to the furnishings since our last stay…it was great before and now that much better. The common space/game room down by the lake was new this year and was a nice add for a break from the sun. Access to the boat slip and location on the lake continues to be a huge plus! As usual, we had a great stay and plan to be back next summer!"

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

Kent L.

CA $416

CA $969 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Winchester-Hotels-New-Close-To-Town-Lakefront-Home-Gorgeous-Water-Views-W-Dockboat-Slip.h77863312.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/62000000/61470000/61465300/61465224/7f76a506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/62000000/61470000/61465300/61465224/4569639d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61470000/61465300/61465224/47f972c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, foosball](https://images.trvl-media.com/lodging/62000000/61470000/61465300/61465224/0938507d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub

[](https://www.expedia.ca/Winchester-Hotels-Amazing-Tims-Ford-Lake-Home-Built-2021-Private-Covered-Dock-Hot-Tub.h61465224.Hotel-Information)

Winchester

9.8/10

Exceptional

(78 reviews)

"Private, beautiful setting"

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

Jeremy L.

CA $751

CA $1,516 total

includes taxes & fees

Jan 14 - Jan 15

[](https://www.expedia.ca/Winchester-Hotels-Amazing-Tims-Ford-Lake-Home-Built-2021-Private-Covered-Dock-Hot-Tub.h61465224.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68150000/68150000/68149945/7a1d4512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/69000000/68150000/68150000/68149945/w1101h754x11y20-812be887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/69000000/68150000/68150000/68149945/64224ed9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68150000/68150000/68149945/3596bf03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakefront Luxury on Tims Ford Lake

[](https://www.expedia.ca/Winchester-Hotels-Lakefront-Luxury-On-Tims-Ford-Lake.h68149945.Hotel-Information)

Winchester

10/10

Exceptional

(11 reviews)

"Very relaxing stay in a quiet neighborhood on the lake. The house is very nice and as advertised. Owner is very communicative and helpful."

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

Clay W.

CA $438

CA $914 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Winchester-Hotels-Lakefront-Luxury-On-Tims-Ford-Lake.h68149945.Hotel-Information)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/78000000/77870000/77863400/77863309/2fc8c2fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/78000000/77870000/77863400/77863309/ccf2ed18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/78000000/77870000/77863400/77863309/716d50b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/78000000/77870000/77863400/77863309/abfaf180.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lake View Prime Location, Community Dock w swim ladders, covered boat slip, 

[](https://www.expedia.ca/Winchester-Hotels-New-Tranquil-Lakefront-Home-Close-To-Town.h77863309.Hotel-Information)

Winchester

10/10

Exceptional

(23 reviews)

"My family came in from Virginia and some friends came from Kentucky for the Memorial Day weekend. We absolutely loved the house it’s beautiful, the view was so beautiful the host was so very nice and made sure everything was perfect. I highly recommend this house. We will be back "

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

Tammy B.

CA $417

CA $971 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Winchester-Hotels-New-Tranquil-Lakefront-Home-Close-To-Town.h77863309.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/46000000/45180000/45178100/45178084/608a8b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/46000000/45180000/45178100/45178084/85947b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45180000/45178100/45178084/535092a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45180000/45178100/45178084/9c11555a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24

[](https://www.expedia.ca/Sewanee-Hotels-Pet-Friendly-Near-The-University-Of-The-South.h45178084.Hotel-Information)

Sewanee

9.8/10

Exceptional

(19 reviews)

"Loved this place. Comfortable for just the two of us. Efficient use of space made it feel bigger. Nice touches throughout."

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

Eric G.

CA $124

CA $318 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Sewanee-Hotels-Pet-Friendly-Near-The-University-Of-The-South.h45178084.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108870000/108865900/108865836/7c57a8bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108870000/108865900/108865836/868ea02d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108870000/108865900/108865836/d18b20c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108870000/108865900/108865836/acbbe699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Flat Branch Lodge - Tracy City, TN

[](https://www.expedia.ca/Tracy-City-Hotels-Flat-Branch-Lodge-Tracy-City.h108865836.Hotel-Information)

Tracy City

9.8/10

Exceptional

(16 reviews)

"Great cabin and location for those interested in hiking and resting in a quiet, peaceful location!"

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

Elizabeth T.

CA $96

CA $263 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Tracy-City-Hotels-Flat-Branch-Lodge-Tracy-City.h108865836.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110860000/110852000/110851994/155acc25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110860000/110852000/110851994/0ed939eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110860000/110852000/110851994/26ae0b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/111000000/110860000/110852000/110851994/3e8d67b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Cabin in Tracy City

[](https://www.expedia.ca/Tracy-City-Hotels-The-Cabin-In-Tracy-City.h110851994.Hotel-Information)

Tracy City

9.6/10

Exceptional

(15 reviews)

"Well made cabin, very cute and cozy! Would definitely stay again"

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

Laura

CA $82

CA $228 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Tracy-City-Hotels-The-Cabin-In-Tracy-City.h110851994.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121720000/121713800/121713767/7f691905.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121720000/121713800/121713767/f014f346.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121720000/121713800/121713767/b3c3e0e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121720000/121713800/121713767/8843a0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cumberland Forest Cottage - Quiet & Sizable Back Yard!

[](https://www.expedia.ca/Monteagle-Hotels-Cumberland-Forest-Cottage-Quiet-Sizable-Back-Yard.h121713767.Hotel-Information)

Monteagle

10/10

Exceptional

(1 review)

"The house was spotless and we are very pleased with our stay"

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

Dennis

CA $90

CA $288 total

includes taxes & fees

Jan 14 - Jan 15

[](https://www.expedia.ca/Monteagle-Hotels-Cumberland-Forest-Cottage-Quiet-Sizable-Back-Yard.h121713767.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/119000000/118630000/118628500/118628470/b63b10b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118630000/118628500/118628470/8db66a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/119000000/118630000/118628500/118628470/25a4a7c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118630000/118628500/118628470/e7b992bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tiny Home in Deer Lick Falls Community

[](https://www.expedia.ca/Monteagle-Hotels-Tiny-Home-In-Deer-Lick-Falls-Community.h118628470.Hotel-Information)

Monteagle

10/10

Exceptional

(2 reviews)

"Great Tiny home. We enjoyed the hike to Seer Lick Falls and the home was perfect. Thanks so much "

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

Kristy C.

CA $77

CA $223 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Monteagle-Hotels-Tiny-Home-In-Deer-Lick-Falls-Community.h118628470.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=2026-01-26&endDate=2026-01-27&regionId=177515&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in

](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Vacation-Rentals.d177515.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Vacation-Rentals.d177515.Travel-Guide-VacationRentals)

## Top Winchester Hotel Reviews

![Hampton Inn Kimball](https://images.trvl-media.com/lodging/7000000/6620000/6619800/6619724/bdd47495_y.jpg)

### Hampton Inn Kimball

10/10 Excellent

"Hotel is very clean. Check in super fast and easy. Room was excellent. "

[](https://expedia.ca/Chattanooga-Hotels-Hampton-Inn-Kimball.h6619724.Hotel-Information)

![Comfort Suites Manchester near Arnold AFB](https://images.trvl-media.com/lodging/3000000/2570000/2561100/2561048/527e1a97_y.jpg)

### Comfort Suites Manchester near Arnold AFB

10/10 Excellent

"Room was very clean, i just had a banana and juice. The heater worked great we only stayed one night loved the location had plenty of places to eat"

[](https://expedia.ca/Tullahoma-Hotels-Comfort-Suites-Manchester.h2561048.Hotel-Information)

![The Smokehouse Lodge and Cabins](https://images.trvl-media.com/lodging/1000000/580000/574500/574462/d6395701_y.jpg)

### The Smokehouse Lodge and Cabins

10/10 Excellent

"Absolutely adorable cabins! Staff was great and the smoke house restaurant was cozy, good food and nice live music! "

[](https://expedia.ca/Tullahoma-Hotels-The-Smokehouse-Lodge-And-Cabins.h574462.Hotel-Information)

![Quality Inn Monteagle](https://images.trvl-media.com/lodging/32000000/31430000/31427300/31427211/1785102f_y.jpg)

### Quality Inn Monteagle

10/10 Excellent

"Perfect."

[](https://expedia.ca/Tullahoma-Hotels-Quality-Inn.h31427211.Hotel-Information)

![Microtel Inn & Suites by Wyndham Manchester](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916021/4fbfd2df_y.jpg)

### Microtel Inn & Suites by Wyndham Manchester

10/10 Excellent

"Nice room, very comfortable bed, decent breakfast. "

[](https://expedia.ca/Tullahoma-Hotels-Microtel-Inn-Suites-By-Wyndham-Manchester.h1916021.Hotel-Information)

![Spark by Hilton Kimball](https://images.trvl-media.com/lodging/1000000/450000/446200/446165/63e6edb3_y.jpg)

### Spark by Hilton Kimball

10/10 Excellent

"Great place"

[](https://expedia.ca/Chattanooga-Hotels-Best-Western-Kimball-Inn.h446165.Hotel-Information)

![Holiday Inn Express & Suites Manchester by IHG](https://images.trvl-media.com/lodging/1000000/800000/793800/793725/bf24927c_y.jpg)

### Holiday Inn Express & Suites Manchester by IHG

10/10 Excellent

"Tv needs to be looked at. Not working properly "

[](https://expedia.ca/Tullahoma-Hotels-Holiday-Inn-Express-Suites-Manchester.h793725.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB](https://images.trvl-media.com/lodging/93000000/92460000/92450300/92450290/35585849_y.jpg)

### La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

10/10 Excellent

"Pet friendly, but $25 per pet charge"

[](https://expedia.ca/Manchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Manchester.h92450290.Hotel-Information)

![LivSmart Studios by Hilton Tullahoma](https://images.trvl-media.com/lodging/116000000/115180000/115170800/115170786/w3837h2556x3y3-42f11d30_y.jpg)

### LivSmart Studios by Hilton Tullahoma

10/10 Excellent

"Clean room!! Great staff"

[](https://expedia.ca/Tullahoma-Hotels-Livsmart-Suites-Tullahoma.h115170786.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.   

## Explore a world of travel with Expedia

- Trending destinations on Expedia.ca
- All accommodation types in Winchester

### Trending destinations on Expedia.ca

- [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals)
- [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)
- [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals)
- [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals)
- [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals)
- [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals)
- [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations)
- [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals)
- [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals)
- [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals)
- [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals)
- [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals)
- [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals)
- [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals)
- [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals)
- [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
- [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Winchester ](https://expedia.ca/Winchester-Private-Vacation-Homes.d177515-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cabin Rentals in Winchester ](https://expedia.ca/Winchester-Cabins.d177515-aaCabins.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.ca/Winchester-Cottages.d177515-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.ca/Winchester-Apartments.d177515-aaApartments.Travel-Guide-Accommodation)
- [Farmstay in Winchester ](https://expedia.ca/Winchester-Agritourism.d177515-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.ca/Winchester-Motels.d177515-aaMotels.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.ca/Winchester-Bed-And-Breakfast.d177515-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Hostels in Winchester ](https://expedia.ca/Winchester-Hostels.d177515-aaHostels.Travel-Guide-Accommodation)
- [RV Parks in Winchester ](https://expedia.ca/Winchester-RV-Parks.d177515-aaRVParks.Travel-Guide-Accommodation)
- [Chalets in Winchester ](https://expedia.ca/Winchester-Chalets.d177515-aaChalets.Travel-Guide-Accommodation)
- [Lodges in Winchester ](https://expedia.ca/Winchester-Lodges.d177515-aaLodges.Travel-Guide-Accommodation)
- [Aparthotels in Winchester ](https://expedia.ca/Winchester-Apart-Hotels.d177515-aaApartHotels.Travel-Guide-Accommodation)
- [Inns in Winchester ](https://expedia.ca/Winchester-Inns.d177515-aaInns.Travel-Guide-Accommodation)
- [Condo Rentals in Winchester ](https://expedia.ca/Winchester-Condos.d177515-aaCondos.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Winchester?

### What are some of the best vacation home rentals in Winchester?

### How many vacation rentals are there in Winchester?

### What can I see and do in Winchester?

### What are vacation rentals like in Winchester?

### Expedia's Latest Trends

Hotels

- [Hotels in Honolulu](https://expedia.ca/Honolulu-Hotels.d1488.Travel-Guide-Hotels)
- [Hotels in Bangor](https://expedia.ca/Bangor-Hotels.d6050918.Travel-Guide-Hotels)
- [Hotels in Grand Forks](https://expedia.ca/Grand-Forks-Hotels.d1312.Travel-Guide-Hotels)
- [Hotels in Fargo](https://expedia.ca/Fargo-Hotels.d6059376.Travel-Guide-Hotels)
- [Hotels in Chattanooga](https://expedia.ca/Chattanooga-Hotels.d827.Travel-Guide-Hotels)
- [Hotels in Pigeon Forge](https://expedia.ca/Pigeon-Forge-Hotels.d8264.Travel-Guide-Hotels)
- [Hotels in Palm Springs](https://expedia.ca/Palm-Springs-Hotels.d180676.Travel-Guide-Hotels)
- [Hotels in Knoxville](https://expedia.ca/Knoxville-Hotels.d602977.Travel-Guide-Hotels)
- [Hotels in Gatlinburg](https://expedia.ca/Gatlinburg-Hotels.d7474.Travel-Guide-Hotels)

Flights

- [Cheap Flights to Bristol](https://expedia.ca/Cheap-Flights-To-Bristol.d6372.Travel-Guide-Flights)
- [Cheap Flights to Chattanooga](https://expedia.ca/Cheap-Flights-To-Chattanooga.d827.Travel-Guide-Flights)
- [Cheap Flights to Knoxville](https://expedia.ca/Cheap-Flights-To-Knoxville.d602977.Travel-Guide-Flights)
- [Cheap Flights to Gatlinburg](https://expedia.ca/Cheap-Flights-To-Gatlinburg.d7474.Travel-Guide-Flights)
- [Cheap Flights to Manchester](https://expedia.ca/Cheap-Flights-To-Manchester.d8460.Travel-Guide-Flights)
- [Cheap Flights to Greeneville](https://expedia.ca/Cheap-Flights-To-Greeneville.d7439.Travel-Guide-Flights)
- [Cheap Flights to McMinnville](https://expedia.ca/Cheap-Flights-To-McMinnville.d9701.Travel-Guide-Flights)
- [Cheap Flights to Pigeon Forge](https://expedia.ca/Cheap-Flights-To-Pigeon-Forge.d8264.Travel-Guide-Flights)
- [Cheap Flights to Johnson City](https://expedia.ca/Cheap-Flights-To-Johnson-City.d6089.Travel-Guide-Flights)

Cars

- [Car rentals in Palm Springs](https://expedia.ca/Car-Rentals-In-Palm-Springs.d180676.Car-Rental-Guide)

Activities

- [Things to do in Chattanooga](https://expedia.ca/Things-To-Do-In-Chattanooga.d827.Travel-Guide-Activities)
- [Things to do in Pigeon Forge](https://expedia.ca/Things-To-Do-In-Pigeon-Forge.d8264.Travel-Guide-Activities)
- [Things to do in Knoxville](https://expedia.ca/Things-To-Do-In-Knoxville.d602977.Travel-Guide-Activities)

Packages

- [Disney Vacations](https://expedia.ca/Disney.d3000453867.Destination-Travel-Guides)
- [Pigeon Forge Vacations](https://expedia.ca/Pigeon-Forge.d8264.Destination-Travel-Guides)
- [Central Vacations](https://expedia.ca/Central.d10503.Destination-Travel-Guides)
- [Canadian Vacations](https://expedia.ca/Canadian.d6127256.Destination-Travel-Guides)

General

- [Visit Sneedville](https://expedia.ca/Sneedville.dx3000353639)
- [Visit Quebeck](https://expedia.ca/Quebeck.dx3000353620)
- [Visit Pigeon Forge](https://expedia.ca/Pigeon-Forge.dx8264)
- [Visit Chattanooga](https://expedia.ca/Chattanooga.dx827)

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app