Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Winchester

Interior
Gorgeous Renovated Home with Open Floor Plan and Large Lot

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 ￥17,643
￥52,683 total
includes taxes & fees
Nov 11 - Nov 12
Gorgeous Renovated Home with Open Floor Plan and Large Lot
Marina
Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

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
Smart TV, fireplace, video games, DVD player
Beautiful Lake Views at Twin Creeks!

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!
Outdoor dining
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

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

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
Outdoor dining
"The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake

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 ￥42,191
￥79,854 total
includes taxes & fees
Nov 11 - Nov 12
"The Hawk Nest" cabin on Tims Ford Lake
Fridge, microwave, oven, stovetop
Modern Charm with Rare Flat Lot, Dock, Game Area

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
Private kitchen
Ambassador Inn And Suites

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 ￥8,788
￥10,573 total
includes taxes & fees
Nov 11 - Nov 12
Ambassador Inn And Suites
Couples treatment rooms, hot stone massages, deep-tissue massages
Sasquatch Farm

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 ￥26,849
￥30,809 total
includes taxes & fees
Nov 11 - Nov 12
Sasquatch Farm
Property grounds
Dove Treehouse: Treetop Bliss on Monteagle

Dove Treehouse: Treetop Bliss on Monteagle

Monteagle
9.8 out of 10, Exceptional, (277)
"Very peaceful stay. Quaint treehouse style cabin. Loved the private hot tub right outside the room and the large tiled shower. Kitchen was equipped for us to cook a dinner. It could use plastic cups to take to the hot tub, though. :)A perfect setup for an anniversary trip. Thanks!"
United States
Andrew P.
The price is ￥26,235
￥45,577 total
includes taxes & fees
Dec 1 - Dec 2
Dove Treehouse: Treetop Bliss on Monteagle
Outdoor spa tub
Scandinavian Treetop Bliss @ Terralodge

Scandinavian Treetop Bliss @ Terralodge

Monteagle
9.8 out of 10, Exceptional, (11)
"Impressive "
United States
Robert Y.
The price is ￥15,342
￥32,577 total
includes taxes & fees
Dec 1 - Dec 2
Scandinavian Treetop Bliss @ Terralodge
Pool
Hummingbird Treehouse w/ Hot Tub & Firepit

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.
The price is ￥26,964
￥46,720 total
includes taxes & fees
Nov 17 - Nov 18
Hummingbird Treehouse w/ Hot Tub & Firepit
Exterior
Hemlock Falls LLC 25 mi. From Chattanooga. 2 miles from Foster Falls State Park

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
Property grounds
A very rustic converted pole barn unique cozy cabin

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 ￥14,575
￥24,471 total
includes taxes & fees
Nov 11 - Nov 12
A very rustic converted pole barn unique cozy cabin
Smart TV, fireplace
Monteagle Cabin, Views! Hot Tub!

Monteagle Cabin, Views! Hot Tub!

Monteagle
10.0 out of 10, Exceptional, (42)
"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!
Property grounds
Eagle Treehouse: Hot Tub, Fireplace, and Outdoor Firepit!

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.
The price is ￥26,089
￥45,102 total
includes taxes & fees
Dec 8 - Dec 9
Eagle Treehouse: Hot Tub, Fireplace, and Outdoor Firepit!
Exterior
Escape to Banjo Bungalow your cozy 2-bdrm lakefront cabin on 27 private acres

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
Property grounds
Tiny Home in Deer Lick Falls Community

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 ￥11,967
￥28,536 total
includes taxes & fees
Dec 1 - Dec 2
Tiny Home in Deer Lick Falls Community
Exterior
Hollerback Hunt & Yacht Club, peaceful lakefront with private dock on 6 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
Terrace/patio
1 Room Camping Cabin - Enjoy a cabin with air conditioning and real beds!

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

Manchester
The price is ￥7,671
￥11,680 total
includes taxes & fees
Nov 11 - Nov 12
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

Spark by Hilton Kimball

Spark by Hilton Kimball

10/10 Excellent
"Nice staff, clean room, breakfast with limited sitting and options if you come at popular hours"
Alain 1-night trip
Posted 1 day ago
Spark by Hilton Kimball

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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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?

Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs: Visitors like this Winchester vacation home rental. It is located on a lake and has a balcony, an arcade game room, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind. Some other top choices in Winchester are Beautiful Lake Views at Twin Creeks! and Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre.

How many vacation rentals are there in Winchester?

Expedia has 117 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 Harvey's Garden and Tims Ford are a couple of great spots to enjoy the outdoors. Other places in town to visit include Tims Ford State Park and Tims Ford Lake.

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.