Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Winchester vacation rentals

Microwave, oven, stovetop, dishwasher

Tiny Home w/ RV Hookups

Tiny Home w/ RV Hookups
Winchester
9.0 out of 10, Wonderful, (9 reviews)
"Great place to stay! "
United States
Erica P.
The price is ￥16,838
￥33,686 total
includes taxes & fees
Feb 10 - Feb 11
Tiny Home w/ RV Hookups
Outdoor dining

"The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake
Winchester
9.6 out of 10, Exceptional, (18 reviews)
"Very cozy and great lake location. We definitely plan to go back."
United States
Jason G.
The price is ￥17,137
￥48,190 total
includes taxes & fees
Feb 10 - Feb 11
"The Hawk Nest" cabin on Tims Ford Lake
Fridge, microwave, oven, stovetop

Oasis on the Square

Oasis on the Square
Winchester
9.8 out of 10, Exceptional, (12 reviews)
"Great love the location "
United States
Zita L.
The price is ￥12,681
￥27,232 total
includes taxes & fees
Feb 16 - Feb 17
Oasis on the Square
Fridge, microwave, oven, stovetop

Lakeside Luxe - Lake Access + Community Pool

Lakeside Luxe - Lake Access + Community Pool
Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Had a great stay and would recommend this property to all!"
United States
Lizzie S.
The price is ￥24,762
￥95,362 total
includes taxes & fees
Feb 10 - Feb 11
Lakeside Luxe - Lake Access + Community Pool
Microwave, stovetop, paper towels

Luxurious Winter Retreat/ Lynchburg, TN

Luxurious Winter Retreat/ Lynchburg, TN
Winchester
The price is ￥17,687
￥23,043 total
includes taxes & fees
Feb 10 - Feb 11
Luxurious Winter Retreat/ Lynchburg, TN
Terrace/patio

Gather at Tims Ford Lake

Gather at Tims Ford Lake
Winchester
9.6 out of 10, Exceptional, (19 reviews)
"Great house for our family. We enjoyed our week at the lake!"
United States
Debra G.
The price is ￥41,317
￥103,158 total
includes taxes & fees
Feb 10 - Feb 11
Gather at Tims Ford Lake
Interior

Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.8 out of 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
Jennifer M.
The price is ￥14,283
￥29,082 total
includes taxes & fees
Feb 22 - Feb 23
Winchester's Premier Downtown Loft!
Interior

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

Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Winchester
10.0 out of 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
Gwen K.
The price is ￥46,694
￥120,598 total
includes taxes & fees
Feb 10 - Feb 11
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Terrace/patio

Lakefront Luxury on Tims Ford Lake

Lakefront Luxury on Tims Ford Lake
Winchester
10.0 out of 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
Clay W.
The price is ￥49,524
￥105,131 total
includes taxes & fees
Feb 10 - Feb 11
Lakefront Luxury on Tims Ford Lake
Smart TV, fireplace

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

Cozy 2-bedroom RV in awesome Winchester with WiFi, AC
Winchester
The price is ￥15,423
￥28,386 total
includes taxes & fees
Feb 11 - Feb 12
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC
Property grounds

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

Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Winchester
10.0 out of 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
Kent L.
The price is ￥47,009
￥109,076 total
includes taxes & fees
Feb 10 - Feb 11
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Outdoor dining

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

Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Winchester
9.8 out of 10, Exceptional, (78 reviews)
"Private, beautiful setting"
United States
Jeremy L.
The price is ￥84,899
￥171,606 total
includes taxes & fees
Feb 10 - Feb 11
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Smart TV, table tennis

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

Lake View Prime Location, Community Dock w swim ladders, covered boat slip,
Winchester
10.0 out of 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
Tammy B.
The price is ￥47,166
￥109,258 total
includes taxes & fees
Feb 10 - Feb 11
Lake View Prime Location, Community Dock w swim ladders, covered boat slip,
Smart TV, books

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

Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
Sewanee
9.8 out of 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
Eric G.
The price is ￥14,008
￥35,984 total
includes taxes & fees
Feb 22 - Feb 23
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
Executive Apartment, 2 Queen Beds | Individually decorated, individually furnished, desk, laptop workspace

Ambassador Inn And Suites

Ambassador Inn And Suites
3.5 star property
Manchester
6.4 out of 10, (289 reviews)
"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
Bridget
The price is ￥8,499
￥10,050 total
includes taxes & fees
Feb 10 - Feb 11
Ambassador Inn And Suites
Smart TV

Lydia's Lodge in Pelham

Lydia's Lodge in Pelham
Pelham
9.8 out of 10, Exceptional, (7 reviews)
"Nice, quiet stay. House was very nice"
United States
Sammy K.
The price is ￥10,848
￥34,588 total
includes taxes & fees
Feb 10 - Feb 11
Lydia's Lodge in Pelham
Terrace/patio

Flat Branch Lodge - Tracy City, TN

Flat Branch Lodge - Tracy City, TN
Tracy City
9.8 out of 10, Exceptional, (16 reviews)
"Just a lovely stay enjoyed every moment "
United States
Justin D.
The price is ￥11,005
￥30,186 total
includes taxes & fees
Feb 10 - Feb 11
Flat Branch Lodge - Tracy City, TN
Smart TV

Settle Down on the Lake – Your Waterfront Escape in Tracy City

Settle Down on the Lake – Your Waterfront Escape in Tracy City
Tracy City
10.0 out of 10, Exceptional, (3 reviews)
"Perfect overnight for relaxing, kayaking, football, snore and dinner before a concert at The Caverns on Sunday night. The master bed was incredibly comfortable, owners were super responsive and accommodating. Views are amazing! Would return to this property!"
United States
Melissa F.
The price is ￥26,570
￥52,983 total
includes taxes & fees
Feb 15 - Feb 16
Settle Down on the Lake – Your Waterfront Escape in Tracy City
Smart TV

The Cabin in Tracy City

The Cabin in Tracy City
Tracy City
9.6 out of 10, Exceptional, (16 reviews)
"Well made cabin, very cute and cozy! Would definitely stay again"
United States
Laura
The price is ￥8,490
￥24,998 total
includes taxes & fees
Feb 16 - Feb 17
The Cabin in Tracy City
Interior

The Mountaineer at The Retreat at Deer Lick Falls II

The Mountaineer at The Retreat at Deer Lick Falls II
Monteagle
10.0 out of 10, Exceptional, (9 reviews)
"This was an awesome property! Super cute, comfy, hot tub, fire pit and good location. Really enjoyed our stay here!"
United States
Steve and Shannon B.
The price is ￥16,665
￥56,308 total
includes taxes & fees
Feb 10 - Feb 11
The Mountaineer at The Retreat at Deer Lick Falls II
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.
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Top Winchester Hotel Reviews

Quality Inn Monteagle

Quality Inn Monteagle

10/10 Excellent
"Good value. Will stay again. "
Jennifer 1-night trip
Posted 6 days ago
Quality Inn Monteagle

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we have vacation rentals in Winchester close to Hammers, or you can select a secluded option if you're looking for extra privacy while you relax. Winchester is known for its theme park and lake views. Make sure you have time to check out the university setting and coffeehouses during your trip.

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

Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs: Visitors like this Winchester vacation home rental. It is located on a lake and has a balcony, an arcade game room, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind. Some other top choices in Winchester are Reflection Bay-Dock, Hot Tub, Kayaks and Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak.

How many vacation rentals are there in Winchester?

Expedia has 105 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

Family-friendly attractions include Hammers and Twin Creeks Marina, whereas Tims Ford and Tims Ford Lake are a couple of great spots to enjoy the outdoors. Other places in town to visit include Tim's Ford Marina and Tims Ford State Park.

What are vacation rentals like in Winchester?

Vacation rentals are private accommodations you can reserve for a short or long stay in Winchester. Vacation rentals feature extras like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family gatherings.