Winchester Holiday Rentals

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Holiday Rentals in Winchester

Gorgeous Renovated Home with Open Floor Plan and Large Lot

Winchester
9.0 out of 10, Wonderful, (16)
"Great potential for outside features (firepits, grills, yard games)."
United States
Darrin S.
The price is NZ$609
includes taxes & fees
16 Nov - 17 Nov
Gorgeous Renovated Home with Open Floor Plan and Large Lot

Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

2.0 star property
Winchester
10.0 out of 10, Exceptional, (5)
"This was a great property for our women's retreat! Property was exactly as described!"
United States
Dawn M.
Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

Beautiful Lake Views at Twin Creeks!

Winchester
10.0 out of 10, Exceptional, (56)
"What a wonderful home and neighborhood! Everyone we met was friendly and welcoming. We had a great weekend and hope to call Winchester home one day."
United States
tracy w.
Beautiful Lake Views at Twin Creeks!

Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

2.0 star property
Winchester
10.0 out of 10, Exceptional, (6)
"This property is spectacular. Justin and Derrick were fantastic hosts and were both extremely responsive. We had a minor issue with the theater (by our own doing) and they had someone out to the property within a couple hours to get everything fixed up and running for us.Our group ranged from 65 years young to a 1 year old. This house really is good for all ages. More amenities than i can count. It was easy to get lost in the house as there is plenty of room for everyone. We had 16 people in...
United States
Chad H.
Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

2.0 star property
Winchester
10.0 out of 10, Exceptional, (18)
"Wonderful home and amazing dock located on Tim's Ford Lake. "
United States
Jennifer F.
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

"The Hawk Nest" cabin on Tims Ford Lake

Winchester
9.6 out of 10, Exceptional, (18)
"We love being out in the trees and spending time with nature. This is the perfect spot to just sit back and relax surrounded by trees. "
United States
Jana R.
The price is NZ$923
includes taxes & fees
9 Nov - 10 Nov
"The Hawk Nest" cabin on Tims Ford Lake

Modern Charm with Rare Flat Lot, Dock, Game Area

Winchester
10.0 out of 10, Exceptional, (3)
"Beautiful and convenient location! It's a great place to gather with family and to enjoy some down time. The home is nicely appointed and designed for guests' comfort. We especially loved the game room and the outdoor spaces I'd definitely choose to visit again."
United States
Claire W.
Modern Charm with Rare Flat Lot, Dock, Game Area

Ambassador Inn And Suites

3.5 star property
Manchester
6.4 out of 10, (280)
"Room had about 4 cockroaches chilling on the floor as I walked in. Room also smelled of literal arse. Go down the road there’s a nice place there you’ll thank yourself. Receptionist was nice though. Helped me out with a refund. Fair play. "
United Kingdom
Ryan
The price is NZ$122
includes taxes & fees
9 Nov - 10 Nov
Ambassador Inn And Suites

Sasquatch Farm

3.0 star property
South Pittsburg
8.0 out of 10, Very good, (2)
"loved the place and area, only issue was it did seem like it wasn’t properly cleaned before we arrived and found someone’s socks under the pull out couch. But overall everything else was great! "
United States
Mayumi
The price is NZ$356
includes taxes & fees
9 Nov - 10 Nov
Sasquatch Farm

Scandinavian Treetop Bliss @ Terralodge

Monteagle
9.8 out of 10, Exceptional, (11)
"Impressive "
United States
Robert Y.
The price is NZ$377
includes taxes & fees
1 Dec - 2 Dec
Scandinavian Treetop Bliss @ Terralodge

Hemlock Falls LLC 25 mi. From Chattanooga. 2 miles from Foster Falls State Park

Sequatchie
10.0 out of 10, Exceptional, (160)
"Beautiful cabin, wonderful place, peaceful, breathtaking views, great locstion"
United States
Sheila H.
Hemlock Falls LLC 25 mi. From Chattanooga. 2 miles from Foster Falls State Park

Hummingbird Treehouse w/ Hot Tub & Firepit

Monteagle
10.0 out of 10, Exceptional, (363)
"Loved the location. Will stay again sometime."
United States
Sherry G.
Hummingbird Treehouse w/ Hot Tub & Firepit

Monteagle Cabin, Views! Hot Tub!

Monteagle
10.0 out of 10, Exceptional, (41)
"Four of us stayed for a perfect mama-daughter weekend. Such a thoughtful and comfortable property, perfectly clean and welcoming. Very clear instructions. We loved our stay!!!"
United States
Allison P.
Monteagle Cabin, Views! Hot Tub!

A very rustic converted pole barn unique cozy cabin

Estill Springs
10.0 out of 10, Exceptional, (143)
"This place is the best place ever. My wife and fell in love with this place all of the decor of antique items alot of the stuff that we remembered seeing when we was kids brought back many memories for us"
United States
Kenneth S.
The price is NZ$283
includes taxes & fees
9 Nov - 10 Nov
A very rustic converted pole barn unique cozy cabin

Tiny Home in Deer Lick Falls Community

Monteagle
10.0 out of 10, Exceptional, (2)
"We enjoyed our stay very much! Property was clean and comfortable. We loved the outdoor deck area! Even though there are neighbors, they are not too close. The property is private and secluded and peaceful. There is not a dishwasher which was not an issue for us but we were told to load and turn on before departure which was not possible. I reported that the bathroom faucet dripped constantly and the outside garbage was overflowing but was assured those issues would be resolved. However they did...
United States
Linda T.
The price is NZ$330
includes taxes & fees
1 Dec - 2 Dec
Tiny Home in Deer Lick Falls Community

Eagle Treehouse: Hot Tub, Fireplace, and Outdoor Firepit!

Monteagle
9.8 out of 10, Exceptional, (267)
"This little hideaway was so fantastic. Exactly what we were looking for. Beds were comfy. Hot tub was a major plus after a long day of hiking. My kids really enjoyed the fires at night. 10/10 would go again!"
United States
Kayla C.
Eagle Treehouse: Hot Tub, Fireplace, and Outdoor Firepit!

Escape to Banjo Bungalow your cozy 2-bdrm lakefront cabin on 27 private acres

Altamont
9.6 out of 10, Exceptional, (146)
"Beautiful slice of heaven. My family enjoyed every minute of this place and we will be returning soon"
United States
Lisa S.
Escape to Banjo Bungalow your cozy 2-bdrm lakefront cabin on 27 private acres

Hollerback Hunt & Yacht Club, peaceful lakefront with private dock on 6 Acres

Altamont
9.6 out of 10, Exceptional, (131)
"Enjoyed all the things."
United States
Patti B.
Hollerback Hunt & Yacht Club, peaceful lakefront with private dock on 6 Acres

Caverns,Sewanee,Waterfalls,Fall Hike:Basecamp Tiny

Monteagle
10.0 out of 10, Exceptional, (52)
"Awesome family time and outdoor adventures. Great stay, would come back again!"
United States
Kyle W.
The price is NZ$372
includes taxes & fees
11 Nov - 12 Nov
Caverns,Sewanee,Waterfalls,Fall Hike:Basecamp Tiny

1 Room Camping Cabin - Enjoy a cabin with air conditioning and real beds!

Manchester
The price is NZ$135
includes taxes & fees
17 Nov - 18 Nov
1 Room Camping Cabin - Enjoy a cabin with air conditioning and real beds!
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 favorite 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 depends 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 NZ$122 per night. Entering your travel dates in the search wizard you might find 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?

Gorgeous Renovated Home with Open Floor Plan and Large Lot: This highly rated holiday home rental in Winchester is located on a lake, and has a patio, a selection of games and a BBQ 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 that you can cook with friends or family. Some other top choices in Winchester are Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs and Beautiful Lake Views at Twin Creeks!.

How many holiday rentals are there in Winchester?

Expedia has 117 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.