Title: Winchester Vacation Rentals from CA $89: Short-Term Rentals for 2026 | Expedia.ca

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![High resolution aerial view panorama of lakefront homes, boat docks and beautiful autumn colorful foliage on Tims Ford Lake in Winchester Tennessee USA.](https://images.trvl-media.com/place/177515/c6b76f6b-4f1e-4d6f-ab58-14153246d2cd.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Winchester Vacation Rentals

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## 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

![Private kitchen](https://images.trvl-media.com/lodging/37000000/36060000/36055700/36055683/f36bc70a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Studio Suite](https://images.trvl-media.com/lodging/37000000/36060000/36055700/36055683/89f28eb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/37000000/36060000/36055700/36055683/ab81b411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/37000000/36060000/36055700/36055683/ee267d25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Manchester

[](https://www.expedia.ca/Tullahoma-Hotels-Ambassador-Inn-And-Suites.h36055683.Hotel-Information)

6.4/10

(287)

"The rooms are very nice and clean. The staff here is more then awesome and makes you feel like your home. Everyone goes out of their way to make sure you have everything you need. There is always a person at the front desk 24/7 to help or get whatever you need. Thank you for going above and beyond to make me and my husband feel like we are at home with family. "

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

Bridget

CA $75

CA $89 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Tullahoma-Hotels-Ambassador-Inn-And-Suites.h36055683.Hotel-Information)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116670000/116662100/116662011/20c25430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![58-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/117000000/116670000/116662100/116662011/59be8a9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116670000/116662100/116662011/6e667d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116670000/116662100/116662011/e51d9366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in South Pittsburg

[](https://www.expedia.ca/South-Pittsburg-Hotels-Sasquatch-Farm.h116662011.Hotel-Information)

8.0/10

Very good

(2)

"loved the place and area, only issue was it did seem like it wasn’t properly cleaned before we arrived and found someone’s socks under the pull out couch. But overall everything else was great! "

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

Mayumi

CA $182

CA $209 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/South-Pittsburg-Hotels-Sasquatch-Farm.h116662011.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=2026-01-23&endDate=2026-01-24&regionId=177515&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-04-09&d1=2026-04-09&endDate=2026-04-12&d2=2026-04-12&lodging=CABIN)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-04-09&d1=2026-04-09&endDate=2026-04-12&d2=2026-04-12&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-04-09&d1=2026-04-09&endDate=2026-04-12&d2=2026-04-12&lodging=COTTAGE)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-04-09&d1=2026-04-09&endDate=2026-04-12&d2=2026-04-12&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-04-09&d1=2026-04-09&endDate=2026-04-12&d2=2026-04-12&lodging=APART_HOTEL)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-04-09&d1=2026-04-09&endDate=2026-04-12&d2=2026-04-12&lodging=VILLA)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-04-09&d1=2026-04-09&endDate=2026-04-12&d2=2026-04-12&lodging=CHALET)

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## Top Winchester Hotel Reviews

![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)

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

### Hampton Inn Kimball

10/10 Excellent

"Clean room. "

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

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- [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)
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- [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)
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## Frequently asked questions

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

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

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

### What are vacation rentals like in Winchester?

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