Title: Winchester Vacation Rentals from $68: Search Short-Term Rentals | Expedia.com

[Winchester Travel Guide](https://expedia.com/Winchester.dx177515)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d177515.Travel-Guide-Hotels)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d177515.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d177515.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d177515.Destination-Travel-Guides)

![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)

![](https://images.trvl-media.com/place/177515/c6b76f6b-4f1e-4d6f-ab58-14153246d2cd.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=177515&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/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)

In three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=177515&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 four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=177515&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)

## Our top choices for Winchester vacation rentals

![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)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103950000/103947800/103947795/af1a003a.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)

![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)

### Cottage in Winchester

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

9.0/10

Wonderful

(9 reviews)

"Great place to stay! "

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

Erica P.

$187 nightly

$214 total

Mar 8 - Mar 9

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194115/98903ea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194115/895fbc2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194115/5932e6f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194115/0318c60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winchester

[](https://www.expedia.com/Winchester-Hotels-Beautiful-And-Spacious-Fully-Renovated-Farmhouse.h78194115.Hotel-Information)

9.4/10

Exceptional

(30 reviews)

"Clean, comfortable and 3 bathrooms are a blessing!"

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

julie c.

$322 nightly

$338 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Beautiful-And-Spacious-Fully-Renovated-Farmhouse.h78194115.Hotel-Information)

![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)

![TV](https://images.trvl-media.com/lodging/77000000/76930000/76923600/76923589/c85ef593.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)

### Cabin in Winchester

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

9.4/10

Exceptional

(19 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.

$268 nightly

$307 total

Mar 4 - Mar 5

Total with taxes and fees

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

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/79000000/78200000/78194100/78194091/9cc274bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78200000/78194100/78194091/b02a1ae3.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/79000000/78200000/78194100/78194091/239c468e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/79000000/78200000/78194100/78194091/1872deae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winchester

[](https://www.expedia.com/Winchester-Hotels-Beautifully-Renovated-Studio-2-Miles-From-The-Marina.h78194091.Hotel-Information)

9.8/10

Exceptional

(15 reviews)

"The place was exactly as pictured with an easy check-in and out process. Was a perfect little place for us to stay for a long weekend!"

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

Anonymous traveler

$180 nightly

$191 total

Mar 6 - Mar 7

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Beautifully-Renovated-Studio-2-Miles-From-The-Marina.h78194091.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)

![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)

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

### Apartment in Winchester

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

9.8/10

Exceptional

(12 reviews)

"Great love the location "

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

Zita L.

$154 nightly

$165 total

Mar 5 - Mar 6

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/119000000/118720000/118717600/118717529/f815d1fc.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)

![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)

### Mobile Home in Winchester

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

$158 nightly

$181 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Cozy-2-Bedroom-RV-In-Awesome-Winchester-With-WiFi.h118717529.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/104000000/103850000/103844300/103844252/4aa40d78.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)

![Dining](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844252/ac736384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winchester

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

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.

$168 nightly

$182 total

Mar 4 - Mar 5

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194127/cb8d8d48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194127/dcc8c8db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194127/e944a7f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194127/a8f8fe58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winchester

[](https://www.expedia.com/Winchester-Hotels-Gorgeous-Renovated-Home-With-Open-Floor-Plan-And-Large-Lot.h78194127.Hotel-Information)

8.8/10

Excellent

(19 reviews)

"Great place - quite and relaxing, close to town. The hosts were wonderful, very responsive to any messages and questions! Will definitely return!!"

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

Theresa A.

$309 nightly

$324 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Gorgeous-Renovated-Home-With-Open-Floor-Plan-And-Large-Lot.h78194127.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)

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

![Children's area](https://images.trvl-media.com/lodging/123000000/122340000/122331500/122331485/dd44b8b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mobile Home in Winchester

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

$133 nightly

$147 total

Mar 4 - Mar 5

Total with taxes and fees

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

![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)

![Exterior](https://images.trvl-media.com/lodging/92000000/91120000/91111100/91111096/535332b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winchester

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

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.

$626 nightly

$715 total

Mar 4 - Mar 5

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/108000000/107720000/107712700/107712604/b9b6e640.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)

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

### Vacation Home in Winchester

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

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.

$682 nightly

$767 total

Mar 4 - Mar 5

Total with taxes and fees

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

![Dining](https://images.trvl-media.com/lodging/69000000/68150000/68150000/68149945/64224ed9.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)

![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)

### Vacation Home in Winchester

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

10/10

Exceptional

(14 reviews)

"Awesome lake house!! A great retreat. Will come back someday we hope!! "

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

Tara C.

$626 nightly

$717 total

Mar 4 - Mar 5

Total with taxes and fees

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

![Marina](https://images.trvl-media.com/lodging/109000000/108930000/108926900/108926864/57e497d8.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)

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

### Vacation Home in Winchester

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

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.

$608 nightly

$683 total

Mar 9 - Mar 10

Total with taxes and fees

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

![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/f0fe5154.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)

### Vacation Home in Winchester

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

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.

$610 nightly

$697 total

Mar 4 - Mar 5

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61470000/61465300/61465224/9e723b09.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)

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

### Vacation Home in Winchester

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

9.8/10

Exceptional

(78 reviews)

"Private, beautiful setting"

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

Jeremy L.

$960 nightly

$1,097 total

Mar 4 - Mar 5

Total with taxes and fees

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

![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/78000000/77870000/77863400/77863309/569fc45b.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/abfaf180.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winchester

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

10/10

Exceptional

(23 reviews)

"What a lovely property and the perfect stay for a large family! We had a great time and the host is very gracious and accommodating. The home was well stocked and had all of the amenities we could have wanted. We had no issues, but the host was very communicative and I'm confident any issue would have been resolved promptly. I highly recommend this home, as well as any other listings from this host!"

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

Lisa A.

$611 nightly

$698 total

Mar 4 - Mar 5

Total with taxes and fees

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

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110860000/110852000/110851994/986c49ef.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/111000000/110860000/110852000/110851994/998af097.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Tracy City

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

9.6/10

Exceptional

(16 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

$171 nightly

$171 total

Mar 4 - Mar 5

Total with taxes and fees

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

![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/117000000/116030000/116026100/116026001/3c539cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116030000/116026100/116026001/6a20fe3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116030000/116026100/116026001/8a19cfae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116030000/116026100/116026001/eb0b0c70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Monteagle

[](https://www.expedia.com/Monteagle-Hotels-Deciduous-Dreams-In-Deer-Lick-Falls.h116026001.Hotel-Information)

8.8/10

Excellent

(6 reviews)

"The cabin had a gorgeous outdoor space making the tiny house seem bigger. Nice kitchen and washer dryer. Super cozy. Clean. Would stay again. "

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

Victoria W.

$175 nightly

$175 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Monteagle-Hotels-Deciduous-Dreams-In-Deer-Lick-Falls.h116026001.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95480000/95478100/95478090/0c6301f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/96000000/95480000/95478100/95478090/d166b214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/96000000/95480000/95478100/95478090/1386f454.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/96000000/95480000/95478100/95478090/039b8a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Monteagle

[](https://www.expedia.com/Monteagle-Hotels-Smarter-Than-The-Average-Stay-At-The-Yogi-Cottage.h95478090.Hotel-Information)

9.0/10

Wonderful

(7 reviews)

"We stayed the night to enjoy a concert at the Caverns. The cottage is adorable and the Caverns are amazing. "

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

Rachel C.

$156 nightly

$156 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Monteagle-Hotels-Smarter-Than-The-Average-Stay-At-The-Yogi-Cottage.h95478090.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/30000000/29490000/29482500/29482406/e0c99116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/30000000/29490000/29482500/29482406/d2e28ee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/30000000/29490000/29482500/29482406/5de40ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/30000000/29490000/29482500/29482406/bf11bc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Estill Springs

[](https://www.expedia.com/Estill-Springs-Hotels-Our-Unique-Cozy-Cabin.h29482406.Hotel-Information)

10/10

Exceptional

(149 reviews)

"Relaxing get away...quiet and peaceful you cant get any better than that for a vacation"

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

Cheryl W.

$140 nightly

$160 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Estill-Springs-Hotels-Our-Unique-Cozy-Cabin.h29482406.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=2026-03-17&endDate=2026-03-18&regionId=177515&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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[Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_177515)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=VILLA)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CHALET)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Tennessee%2C+United+States+of+America&regionId=177515&latLong=35.185917%2C-86.112205&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APART_HOTEL)

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## Top Winchester Hotel Reviews

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

### Quality Inn Monteagle

8/10 Good

"Room was clean. Breakfast not so good!"

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

![The Smokehouse Lodge and Cabins](https://images.trvl-media.com/lodging/1000000/580000/574500/574462/aee2f9a7_y.jpg)

### The Smokehouse Lodge and Cabins

10/10 Excellent

"It is an older place but it was clean. The staff was friendly and helpful. It is off season so the restaurant and the pool wasn't open, but I would stay again. Enjoyed it."

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

![Best Western Inn](https://images.trvl-media.com/lodging/1000000/520000/517600/517564/8a05d9db_y.jpg)

### Best Western Inn

8/10 Good

"Nice place. Loved the tables and chairs outside room to sit and enjoy the outdoors. "

[](https://expedia.com/Tullahoma-Hotels-Best-Western-Inn.h517564.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

8/10 Good

"Clean room but surprisingly small. Great value for what we paid and very convenient for visiting The Caverns. "

[](https://expedia.com/Tullahoma-Hotels-Microtel-Inn-Suites-By-Wyndham-Manchester.h1916021.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

"Room was clean and organized with no issues "

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

![The Sewanee Inn](https://images.trvl-media.com/lodging/8000000/7110000/7101200/7101157/d9533550_y.jpg)

### The Sewanee Inn

10/10 Excellent

"we found this place for a one night stay for anniversary. It was perfect. The food was excellent. The staff was friendly. The room was clean, and the hotel itself was quite stunning."

[](https://expedia.com/Tullahoma-Hotels-The-Sewanee-Inn.h7101157.Hotel-Information)

!["The Hawk Nest" cabin on Tims Ford Lake](https://images.trvl-media.com/lodging/77000000/76930000/76923600/76923589/f25ef800_y.jpg)

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

8/10 Good

"We loved the cabin and we want to stay again soon. "

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

![Reflection Bay-Dock, Hot Tub, Kayaks](https://images.trvl-media.com/lodging/106000000/105140000/105132200/105132140/239265ad_y.jpg)

### Reflection Bay-Dock, Hot Tub, Kayaks

10/10 Excellent

"Nice place"

[](https://expedia.com/Winchester-Hotels-Reflection-Bay-Dock.h105132140.Hotel-Information)

![Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK](https://images.trvl-media.com/lodging/82000000/81750000/81748200/81748162/cb5434bd_y.jpg)

### Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK

10/10 Excellent

"This is your rental! Everything was wonderful!"

[](https://expedia.com/Winchester-Hotels-Lakefront-Lakeview-Steps-To-The-Water-Tims-Ford-Lake-LUXURY-Home.h81748162.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 $68 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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- [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)

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

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- [Hotel Rooms in Knoxville](https://expedia.com/Knoxville-Hotels.d602977.Travel-Guide-Hotels)
- [Hotel Rooms in Pigeon Forge](https://expedia.com/Pigeon-Forge-Hotels.d8264.Travel-Guide-Hotels)
- [Gatlinburg Hotels with an Indoor Pool](https://expedia.com/Gatlinburg-Hotels-Hotels-With-Indoor-Pool.0-0-d7474-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
- [Hotel Rooms in Jackson](https://expedia.com/Jackson-Hotels.d6059452.Travel-Guide-Hotels)
- [Hotel Rooms in Gatlinburg](https://expedia.com/Gatlinburg-Hotels.d7474.Travel-Guide-Hotels)
- [Knoxville Cheap Hotels](https://expedia.com/Knoxville-Hotels-Cheap-Hotels.0-0-d602977-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Pigeon Forge Pet-friendly Hotels](https://expedia.com/Pigeon-Forge-Hotels-Pet-Friendly-Hotel.0-0-d8264-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)

Flights

- [Flights to TYS](https://expedia.com/Cheap-Flights-To-Pigeon-Forge.d8264.Travel-Guide-Flights)
- [Flights to CHA](https://expedia.com/Cheap-Flights-To-Chattanooga.d827.Travel-Guide-Flights)
- [Knoxville Cheap Flights](https://expedia.com/lp/flights/602977/flights-from-knoxville)
- [Flights to TYS](https://expedia.com/Cheap-Flights-To-Knoxville.d602977.Travel-Guide-Flights)

Cars

- [Car rentals in Chattanooga](https://expedia.com/Car-Rentals-In-Chattanooga.d827.Car-Rental-Guide)
- [Car rentals in Knoxville](https://expedia.com/Car-Rentals-In-Knoxville.d602977.Car-Rental-Guide)

Activities

- [Things to do in Knoxville](https://expedia.com/Things-To-Do-In-Knoxville.d602977.Travel-Guide-Activities)
- [Things to do in Gatlinburg](https://expedia.com/Things-To-Do-In-Gatlinburg.d7474.Travel-Guide-Activities)
- [Things to do in Chattanooga](https://expedia.com/Things-To-Do-In-Chattanooga.d827.Travel-Guide-Activities)
- [Things to do in Pigeon Forge](https://expedia.com/Things-To-Do-In-Pigeon-Forge.d8264.Travel-Guide-Activities)

Packages

- [Pigeon Forge Packages](https://expedia.com/Pigeon-Forge.d8264.Destination-Travel-Guides)
- [Gatlinburg All Inclusive Vacation Packages](https://expedia.com/lp/theme-vacations/all-inclusive-vacations/7474/Gatlinburg)
- [Gatlinburg Packages](https://expedia.com/Gatlinburg.d7474.Destination-Travel-Guides)

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