A calm lake with autumn foliage, a dock, and houses along the shore.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Winchester vacation rentals

Interior

1. Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.4 out of 10, Exceptional, (16 reviews)
"It was wonderful and right in the center of downtown winchester. Very clean and beautiful loft and amazing lighting to have long night talks. Truly amazing"
United States
Gianmarco
The price is ￥14,657
￥30,001 total
includes taxes & fees
Aug 19 - Aug 20
Winchester's Premier Downtown Loft!
Coffee/tea maker, fridge, microwave, oven

2. Oasis on the Square

Oasis on the Square
Winchester
9.8 out of 10, Exceptional, (13 reviews)
"Great location on the square with plenty of dining options a short walk away."
United States
possible Amanda H
The price is ￥15,629
￥31,284 total
includes taxes & fees
Aug 23 - Aug 24
Oasis on the Square
Microwave, oven, stovetop, dishwasher

3. Tiny Home w/ RV Hookups

Tiny Home w/ RV Hookups
Winchester
9.0 out of 10, Wonderful, (11 reviews)
"Great place to stay! "
United States
Erica P.
The price is ￥14,339
￥29,076 total
includes taxes & fees
Aug 19 - Aug 20
Tiny Home w/ RV Hookups
Smart TV, fireplace, stereo

4. Cozy 2 BR RV near Tims Ford Lake in Winchester with WiFi, AC

Cozy 2 BR RV near Tims Ford Lake in Winchester with WiFi, AC
Winchester
7.0 out of 10, Good, (6 reviews)
"This property was perfect for our family and is very close to the marina. Would definitely stay again! "
United States
Emily C.
The price is ￥15,629
￥26,729 total
includes taxes & fees
Aug 18 - Aug 19
Cozy 2 BR RV near Tims Ford Lake in Winchester with WiFi, AC
Interior

5. 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, (7 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 ￥52,576
￥126,437 total
includes taxes & fees
Sep 13 - Sep 14
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Outdoor dining

6. "The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake
Winchester
9.2 out of 10, Wonderful, (24 reviews)
"Great little, hidden get-away!"
United States
Rich F.
The price is ￥43,813
￥77,463 total
includes taxes & fees
Aug 24 - Aug 25
"The Hawk Nest" cabin on Tims Ford Lake
Property grounds

7. 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, (37 reviews)
"Very nice! "
United States
Adam H.
The price is ￥47,637
￥103,141 total
includes taxes & fees
Sep 13 - Sep 14
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Terrace/patio

8. The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort

The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Winchester
10.0 out of 10, Exceptional, (8 reviews)
"Right on the water and next to the marina, great location! We stayed over Christmas week. We will be returning in the summer so we can enjoy the lake!"
United States
Andy D.
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Outdoor dining

9. 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
10.0 out of 10, Exceptional, (82 reviews)
"We had a great time! "
United States
Cindy O.
The price is ￥86,033
￥162,315 total
includes taxes & fees
Aug 18 - Aug 19
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Terrace/patio

10. Lakefront Lodge on Tims Ford Lake

Lakefront Lodge on Tims Ford Lake
Winchester
10.0 out of 10, Exceptional, (20 reviews)
"This is a fabulous lake house! The view and amenities are perfect! "
United States
Andrea M.
Lakefront Lodge on Tims Ford Lake
House, 5 Bedrooms | Marina

11. Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home

Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
3.0 star property
Winchester
The price is ￥95,092
￥202,928 total
includes taxes & fees
Sep 1 - Sep 2
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
Smart TV, table tennis

12. Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12

Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Winchester
10.0 out of 10, Exceptional, (25 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
Lisa A.
The price is ￥55,762
￥115,814 total
includes taxes & fees
Sep 13 - Sep 14
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Coffee/tea maker, fridge, microwave, oven

13. Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!

Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
Pelham
9.6 out of 10, Exceptional, (35 reviews)
"House is kept in great condition, beautiful location, and perfect stay when attending the caverns (12 minutes away)"
United States
Antonio M.
The price is ￥11,152
￥42,095 total
includes taxes & fees
Aug 18 - Aug 19
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
Outdoor dining

14. A very rustic converted pole barn unique cozy cabin

A very rustic converted pole barn unique cozy cabin
Estill Springs
9.8 out of 10, Exceptional, (162 reviews)
"Our stay was comfortable and clean."
United States
George A.
The price is ￥15,932
￥24,495 total
includes taxes & fees
Aug 18 - Aug 19
A very rustic converted pole barn unique cozy cabin
Interior

15. Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns

Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
Pelham
10.0 out of 10, Exceptional, (6 reviews)
"This place was absolutely beautiful. Perfect size for my husband and I and close proximity to The Caverns. We had a wonderful stay! We will definitely be returning!"
United States
Kimberley D.
The price is ￥10,356
￥30,808 total
includes taxes & fees
Aug 18 - Aug 19
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
Lobby

16. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (24 reviews)
"Great stay "
United States
D K.
The price is ￥12,546
￥33,172 total
includes taxes & fees
Aug 22 - Aug 23
Whiskey Trails Cottage
Smart TV, fireplace, DVD player

17. Deciduous Dreams in Deer Lick Falls

Deciduous Dreams in Deer Lick Falls
Monteagle
9.0 out of 10, Wonderful, (14 reviews)
"Loved our stay here - such a cozy little tiny home community, private but not isolated. We loved the hike to the waterfall on the property grounds, as well as the gorgeous Fiery Gizzard North trailhead with several other waterfalls just a short drive away. "
United States
Claire H.
The price is ￥11,949
￥32,788 total
includes taxes & fees
Aug 23 - Aug 24
Deciduous Dreams in Deer Lick Falls
WiFi (free), bed sheets

18. Sasquatch Farm

Sasquatch Farm
3.0 star property
South Pittsburg
9.4 out of 10, Exceptional, (8 reviews)
"Omgoodness this place is absolutely amazing!!! We went for a spiritual journey and it was perfect!! The lake & water fall creek with seats sitting in the water was perfect for my reading and meditating. It is absolutely beautiful!!! They had a concert Saturday night, we didn't go to the actual concert but was right beside it and they were fabulous!! Great place to stay! We will definitely return. Thank you so much for everything!"
United States
Tina
The price is ￥13,621
￥15,630 total
includes taxes & fees
Aug 26 - Aug 27
Sasquatch Farm
Terrace/patio

19. Smarter than the Average Stay at the Yogi Cottage!

Smarter than the Average Stay at the Yogi Cottage!
Monteagle
9.2 out of 10, Wonderful, (9 reviews)
"We had the best time. The place was really nice. We loved the bear statues that decorated the establishment. Communication was good. Interior was visually appealing."
United States
Shanna R.
The price is ￥10,228
￥31,884 total
includes taxes & fees
Aug 18 - Aug 19
Smarter than the Average Stay at the Yogi Cottage!
Exterior

20. The Woods at The Retreat at Deer Lick Falls

The Woods at The Retreat at Deer Lick Falls
Monteagle
9.8 out of 10, Exceptional, (41 reviews)
"The home was cute, clean and quiet. Would be great for a family but I also enjoyed my stay alone. Love the tiny home neighborhood surrounded by nature."
United States
Skip E.
The price is ￥14,355
￥50,207 total
includes taxes & fees
Aug 24 - Aug 25
The Woods at The Retreat at Deer Lick Falls
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

Best Western Inn

Best Western Inn

10/10 Excellent
"Great staff and the breakfast items were hot and good"
William 2-night trip
Posted 2 days ago
Best Western Inn

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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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we have vacation rentals in Winchester close to Twin Creeks Marina, 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?

Private dock/gazebo on quiet cove. Tims Ford Lake!: Visitors like this Winchester vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Winchester are Lakefront w/Private Dock and Walk to Historic Downtown Winchester! and Spacious Family Gem: Golf Cart - 2 Ensuites - Pool.

How many vacation rentals are there in Winchester?

Expedia has 115 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

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

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.