Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Holiday Home in Winchester

9.0 out of 10, Wonderful, (16)
"Peaceful, relaxing and pet friendly great location!"
United States
Holly M.
The price is €307
includes taxes & fees
23 Nov - 24 Nov
Gorgeous Renovated Home with Open Floor Plan and Large Lot

Holiday Home in Winchester

2.0 star property
10.0 out of 10, Exceptional, (5)
"Great stay!! Plenty of space. Clean. Great location. "
United States
Kelley G.
Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

Holiday Home in Winchester

10.0 out of 10, Exceptional, (56)
"This house has everything! We enjoyed the screened porch each morning with coffee and the lake view. The neighborhood was great for walking the dog. We enjoyed the Bodega close by and the live music at the marina. The town of Winchester is adorable! "
United States
Sheri P.
Beautiful Lake Views at Twin Creeks!

Holiday Home in Winchester

2.0 star property
10.0 out of 10, Exceptional, (19)
"Everything was perfect. We really enjoyed our stay. "
United States
Amy W.
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

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 €460
includes taxes & fees
21 Nov - 22 Nov
"The Hawk Nest" cabin on Tims Ford Lake

Holiday Home in Winchester

2.0 star property
10.0 out of 10, Exceptional, (7)
"Great House - the layout is amazing for a group. We will be back!"
United States
Abigail A.
Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

Holiday Home in Winchester

10.0 out of 10, Exceptional, (4)
"Host was excellent and immediately took care of an inquiry when we reached out. The house was great for my adult family to meet in a neutral location, we especially loved all the games on a rainy day. This home had everything that you could need, was comfortable and well-stocked. Most definitely would book again if we go back to the area. "
United States
Sue H.
Modern Charm with Rare Flat Lot, Dock, Game Area

Aparthotel in Manchester

3.5 star property
6.4 out of 10, (281)
"Cockroaches and numerous assorted small bugs all over end table, floors and on pillows. Dried up food on floor. I checked in but left shortly after. Received a refund. Notified front desk. "
United States
BILLY
The price is €60
includes taxes & fees
21 Nov - 22 Nov
Ambassador Inn And Suites

Cabin in South Pittsburg

3.0 star property
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 €173
includes taxes & fees
23 Nov - 24 Nov
Sasquatch Farm

Cabin in Monteagle

9.8 out of 10, Exceptional, (12)
"Very impressed with the amenities. Everything needed for a wonderfully cozy stay. Hottub was very clean and perfect temp. Loved the attic sleeping area - very comfy bed. Perfect stay!"
United States
Hannah F.
The price is €188
includes taxes & fees
1 Dec - 2 Dec
Scandinavian Treetop Bliss @ Terralodge

Cabin in Monteagle

9.8 out of 10, Exceptional, (277)
"nice secluded property we enjoyed our stay and will be back"
United States
chad r.
The price is €263
includes taxes & fees
1 Dec - 2 Dec
Dove Treehouse: Treetop Bliss on Monteagle

Cabin in Monteagle

9.8 out of 10, Exceptional, (267)
"Close, quite family getaway. "
United States
Jennifer R.
The price is €262
includes taxes & fees
1 Dec - 2 Dec
Eagle Treehouse: Hot Tub, Fireplace, and Outdoor Firepit!

Cabin in Monteagle

10.0 out of 10, Exceptional, (363)
"Property was as described. Easy to access and close to hiking and two towns. Would stay here again. "
United States
Anonymous traveller
The price is €269
includes taxes & fees
24 Nov - 25 Nov
Hummingbird Treehouse w/ Hot Tub & Firepit

Cabin in Estill Springs

10.0 out of 10, Exceptional, (144)
"The space was just what we needed to kick off the NupsWeekend. "
United States
Dwayne
The price is €142
includes taxes & fees
24 Nov - 25 Nov
A very rustic converted pole barn unique cozy cabin

Cabin in Sequatchie

The price is €144
includes taxes & fees
24 Nov - 25 Nov
Private Off-Grid Cabin on a Bluff

Cabin in Monteagle

10.0 out of 10, Exceptional, (42)
"Family of 4. Cabin was very clean and comfortable. The view especially of the sunset is extraordinary. Everything was in good working order. Enough cooking utensils to accommodate any meals you might wish to prepare. Conveniently located near town yet far enough to feel remote. Highly recommend this cabin "
United States
Robert
Monteagle Cabin, Views! Hot Tub!

Cabin in Tracy City

2.0 star property
10.0 out of 10, Exceptional, (1)
"The house was very clean and welcoming. Perfect for a last minute trip. Even our fur baby loves the place and the large back yard. It had everything we needed close to coalmont off road park. "
United States
Jennifer D.
The price is €171
includes taxes & fees
19 Dec - 20 Dec
Battle Cry Cabin – A Civil War Retreat

Cabin in Sequatchie

10.0 out of 10, Exceptional, (160)
"Very nice and clean with beautiful views…"
United States
raymond o.
Hemlock Falls LLC 25 mi. From Chattanooga. 2 miles from Foster Falls State Park

Cabin in Monteagle

10.0 out of 10, Exceptional, (2)
"Great Tiny home. We enjoyed the hike to Seer Lick Falls and the home was perfect. Thanks so much "
United States
Kristy C.
The price is €165
includes taxes & fees
15 Dec - 16 Dec
Tiny Home in Deer Lick Falls Community

Cabin in 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
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, apart-hotels, 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 €60 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 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.