Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Winchester

Exterior
Tiny Home w/ RV Hookups

Cottage in Winchester

8.8 out of 10, Excellent, (8)
"Very clean highly recommend if you are looking to get away and relax "
United States
Jeffrey
$216 nightly
The price is $248
Dec 9 - Dec 10
Total with taxes and fees
Tiny Home w/ RV Hookups
Outdoor dining
"The Hawk Nest" cabin on Tims Ford Lake

Cabin in Winchester

9.6 out of 10, Exceptional, (18)
"This was a nice and very unique place to stay. We really appreciated that we had a place to dock the boat. "
United States
Dawn D. C.
$268 nightly
The price is $307
Dec 8 - Dec 9
Total with taxes and fees
"The Hawk Nest" cabin on Tims Ford Lake
Smart TV, fireplace
The Lakeside Getaway

Vacation Home in Winchester

2.0 star property
9.6 out of 10, Exceptional, (5)
"Incredible "
United States
Jim C.
$404 nightly
The price is $454
Dec 13 - Dec 14
Total with taxes and fees
The Lakeside Getaway
Interior
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp

Vacation Home in Winchester

2.0 star property
10.0 out of 10, Exceptional, (4)
"We were only there for 1 night but the house was clean and comfortable and perfectly suited our needs. "
United States
Gwen K.
$624 nightly
The price is $702
Dec 8 - Dec 9
Total with taxes and fees
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Fridge, microwave, oven, stovetop
Welcome to Tims Ford Lake! Free UTV/kayaks/canoe, firepit, complete privacy!

Vacation Home in Winchester

9.8 out of 10, Exceptional, (13)
"The location is great and peaceful"
United States
Anthony K.
$331 nightly
The price is $378
Dec 8 - Dec 9
Total with taxes and fees
Welcome to Tims Ford Lake! Free UTV/kayaks/canoe, firepit, complete privacy!
Terrace/patio
Lakeview Luxe - Lake Access + Pool

Vacation Home in Winchester

2.0 star property
10.0 out of 10, Exceptional, (3)
"Had a great stay and would recommend this property to all!"
United States
Lizzie S.
$554 nightly
The price is $624
Dec 8 - Dec 9
Total with taxes and fees
Lakeview Luxe - Lake Access + Pool
Dining
Oasis on the Square

Apartment in Winchester

9.6 out of 10, Exceptional, (10)
"Great accommodations in downtown Winchester! "
United States
LeBron F.
$145 nightly
The price is $155
Dec 14 - Dec 15
Total with taxes and fees
Oasis on the Square
Smart TV, fireplace
Luxurious Lakefront Home- Marina, Boats, and Kayaks!

Vacation Home in Winchester

10.0 out of 10, Exceptional, (1)
"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
Gary W.
$433 nightly
The price is $488
Dec 8 - Dec 9
Total with taxes and fees
Luxurious Lakefront Home- Marina, Boats, and Kayaks!
Microwave, stovetop, paper towels
Luxurious Winter Retreat/ Lynchburg, TN

Mobile Home in Winchester

2.0 star property
$133 nightly
The price is $147
Dec 8 - Dec 9
Total with taxes and fees
Luxurious Winter Retreat/ Lynchburg, TN
TV, fireplace
Winchester's Premier Downtown Loft!

Apartment in Winchester

9.6 out of 10, Exceptional, (10)
"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.
$136 nightly
The price is $144
Dec 8 - Dec 9
Total with taxes and fees
Winchester's Premier Downtown Loft!
Property grounds
4-bedroom Lake house in tranquil Winchester with Lakeview's, hot tub, pool.

Vacation Home in Winchester

2.0 star property
10.0 out of 10, Exceptional, (1)
"Very clean, many extras in the house. Nice location, close to Winchester and the marina. We all enjoyed it from 11 years old, teenagers to adults."
United States
Greg S.
$377 nightly
The price is $424
Dec 8 - Dec 9
Total with taxes and fees
4-bedroom Lake house in tranquil Winchester with Lakeview's, hot tub, pool.
Property grounds
Lake View Prime Location, Community Dock w swim ladders, covered boat slip,

Vacation Home in Winchester

10.0 out of 10, Exceptional, (23)
"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.
$608 nightly
The price is $695
Dec 8 - Dec 9
Total with taxes and fees
Lake View Prime Location, Community Dock w swim ladders, covered boat slip,
Outdoor dining
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC

Mobile Home in Winchester

$158 nightly
The price is $181
Dec 8 - Dec 9
Total with taxes and fees
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC
Terrace/patio
Gather at Tims Ford Lake

Vacation Home in Winchester

9.6 out of 10, Exceptional, (19)
"Great house for our family. We enjoyed our week at the lake!"
United States
Debra G.
$1,780 nightly
The price is $2,041
Dec 8 - Dec 9
Total with taxes and fees
Gather at Tims Ford Lake
Terrace/patio
Lakefront Luxury on Tims Ford Lake

Vacation Home in Winchester

10.0 out of 10, Exceptional, (11)
"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.
$715 nightly
The price is $816
Dec 8 - Dec 9
Total with taxes and fees
Lakefront Luxury on Tims Ford Lake
Marina
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort

Vacation Home in Winchester

10.0 out of 10, Exceptional, (8)
"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.
$1,075 nightly
The price is $1,188
Dec 24 - Dec 25
Total with taxes and fees
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Property grounds
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family

Vacation Home in Winchester

10.0 out of 10, Exceptional, (35)
"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.
$574 nightly
The price is $656
Dec 8 - Dec 9
Total with taxes and fees
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
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

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

10/10 Excellent
"Room I reserved was gone, so they upgraded me because I can't do stairs. Was very nice."
Julie 1-night trip
Posted 4 days ago
The Smokehouse Lodge and Cabins

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 $69 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

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?

Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak: Visitors like this Winchester vacation home rental. It is located on a lake and has a fireplace, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other top choices in Winchester are Beautiful Lake Views at Twin Creeks! and Gorgeous Renovated Home with Open Floor Plan and Large Lot.

How many vacation rentals are there in Winchester?

Expedia has 116 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 and Tims Ford Lake are a couple of great spots to enjoy the outdoors. Other places in town to visit include Tims Ford State Park and Elk River.

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.