Winchester Holiday Rentals

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Holiday Rentals in Winchester

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
The price is AU$376
includes taxes & fees
8 Dec - 9 Dec
Tiny Home w/ RV Hookups

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.
The price is AU$470
includes taxes & fees
10 Dec - 11 Dec
"The Hawk Nest" cabin on Tims Ford Lake

Holiday Home in Winchester

2.0 star property
9.6 out of 10, Exceptional, (5)
"Incredible "
United States
Jim C.
The price is AU$667
includes taxes & fees
13 Dec - 14 Dec
The Lakefront Getaway

Holiday 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.
The price is AU$1,068
includes taxes & fees
8 Dec - 9 Dec
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp

Holiday Home in Winchester

9.8 out of 10, Exceptional, (13)
"The location is great and peaceful"
United States
Anthony K.
The price is AU$575
includes taxes & fees
16 Dec - 17 Dec
Welcome to Tims Ford Lake! Free UTV/kayaks/canoe, firepit, complete privacy!

Holiday 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.
The price is AU$949
includes taxes & fees
8 Dec - 9 Dec
Lakeview Luxe - Lake Access + Pool

Apartment in Winchester

9.6 out of 10, Exceptional, (10)
"Great accommodations in downtown Winchester! "
United States
LeBron F.
The price is AU$236
includes taxes & fees
14 Dec - 15 Dec
Oasis on the Square

Holiday 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.
The price is AU$679
includes taxes & fees
12 Dec - 13 Dec
Luxurious Lakefront Home- Marina, Boats, and Kayaks!

Mobile Home in Winchester

2.0 star property
The price is AU$224
includes taxes & fees
8 Dec - 9 Dec
Luxurious Winter Retreat/ Lynchburg, TN

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.
The price is AU$221
includes taxes & fees
8 Dec - 9 Dec
Winchester's Premier Downtown Loft!

Holiday 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.
The price is AU$646
includes taxes & fees
18 Dec - 19 Dec
4-bedroom Lake house in tranquil Winchester with Lakeview's, hot tub, pool.

Holiday 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.
The price is AU$1,057
includes taxes & fees
8 Dec - 9 Dec
Lake View Prime Location, Community Dock w swim ladders, covered boat slip,

Mobile Home in Winchester

The price is AU$275
includes taxes & fees
8 Dec - 9 Dec
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC

Holiday 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.
Gather at Tims Ford Lake

Holiday 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.
The price is AU$1,243
includes taxes & fees
8 Dec - 9 Dec
Lakefront Luxury on Tims Ford Lake

Holiday 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.
The price is AU$1,809
includes taxes & fees
24 Dec - 25 Dec
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort

Holiday 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.
The price is AU$998
includes taxes & fees
8 Dec - 9 Dec
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

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winchester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as AU$98 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals in Winchester close to Twin Creeks Marina, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its theme park and lake views. Make sure you have time to check out the university setting and coffee shops during your trip.

What are some of the best holiday rentals that Winchester has to offer?

Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak: This highly rated holiday home rental in Winchester is located on a lake, and has a fireplace, a selection of games and a BBQ 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 that 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 holiday rentals are there in Winchester?

Expedia has 116 holiday 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 holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for families.