1+ Vacation Rentals Near Winchester |
  1. USA
  2. Tennessee
  3. Tullahoma
  4. Winchester

Lakes Resorts - Vacation Rentals in Winchester

Paradise Resort From US $1,978
         

|
New
House
Paradise Resort
  • Air Conditioner
  • Parking
  • Pool

View Availability
See More Winchester Vacation Rentals

Luxury Places to Stay in Winchester

Over 265+ Luxury Places to Stay in or Near Winchester
Luxury Tim’s Ford Lake front -boat available pls inquire- 3 suites From US $1,383
         

10.0 (15 Reviews)
House
Luxury Tim’s Ford Lake front -boat available pls inquire- 3 suites
  • Air Conditioner
  • Parking
  • TV

View Availability
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort From US $1,133
         

10.0 (8 Reviews)
House
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
  • Air Conditioner
  • Parking
  • TV

View Availability
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub From US $1,097
         

9.8 (78 Reviews)
House
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
New Home, Dock, Home Theatre Projector, Hot Tub, Fire Pit, Kayaks From US $930
         

|
9.8 (12 Reviews)
House
New Home, Dock, Home Theatre Projector, Hot Tub, Fire Pit, Kayaks
  • Air Conditioner
  • Parking
  • Security/Safety

View Availability
Hook Wine and Sinker From US $879
         

|
New
House
Hook Wine and Sinker
  • Air Conditioner
  • Security/Safety
  • Sports/Activities

View Availability
Spacious Lakefront Retreat with Hot Tub and Dock! From US $823
         

|
8.0 (1 Review)
House
Spacious Lakefront Retreat with Hot Tub and Dock!
  • Parking
  • Pet Friendly
  • Accessibility

View Availability
Tim's Ford Lakin' it Easy! From US $811
         

10.0 (19 Reviews)
House
Tim's Ford Lakin' it Easy!
  • Air Conditioner
  • Parking
  • TV

View Availability
Deluxe 5BR Lakefront Home - 2 Docks & Boat Ramp From US $754
         

10.0 (33 Reviews)
House
Deluxe 5BR Lakefront Home - 2 Docks & Boat Ramp
  • Air Conditioner
  • Parking
  • TV

View Availability
See More Winchester Luxury Vacation Rentals
Find More Winchester Villas, Resorts, & Rentals on BedroomVillas

Top-Rated Vacation Rentals with a Pool in Winchester

Over 72+ Top-Rated Vacation Rentals with a Pool in or Near Winchester
Beautiful Lake Townhouse at Twin Creeks Resort From US $394
         

10.0 (88 Reviews)
House
Beautiful Lake Townhouse at Twin Creeks Resort
  • Air Conditioner
  • Parking
  • Pool

View Availability
Easy Peasy -lakefront home Tim’s Ford Lake -golf cart seats 6, in Twin Creeks From US $460
         

10.0 (72 Reviews)
House
Easy Peasy -lakefront home Tim’s Ford Lake -golf cart seats 6, in Twin Creeks
  • Air Conditioner
  • Parking
  • Pool

View Availability
Beautiful Lake Views at Twin Creeks! From US $300
         

10.0 (56 Reviews)
House
Beautiful Lake Views at Twin Creeks!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Waterfront Oasis On Tims Ford Lake: Pool/Kayak! From US $317
         

10.0 (51 Reviews)
House
Waterfront Oasis On Tims Ford Lake: Pool/Kayak!
  • Air Conditioner
  • Parking
  • Pool

View Availability
Spacious Family Gem: Golf Cart - 2 Ensuites - Pool From US $312
         

10.0 (32 Reviews)
House
Spacious Family Gem: Golf Cart - 2 Ensuites - Pool
  • Air Conditioner
  • Parking
  • Pool

View Availability
Spacious Lakefront Retreat w/Hot Tub + Dock! From US $329
         

10.0 (28 Reviews)
House
Spacious Lakefront Retreat w/Hot Tub + Dock!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
NEW! Tim's Ford Lakefront Home From US $537
         

10.0 (19 Reviews)
House
NEW! Tim's Ford Lakefront Home
  • Air Conditioner
  • Parking
  • Pool

View Availability
Dry Jack Tim- Water Views, Pool, Outdoor Fireplace From US $212
         

10.0 (14 Reviews)
Apartment
Dry Jack Tim- Water Views, Pool, Outdoor Fireplace
  • Air Conditioner
  • Parking
  • Pool

View Availability
See More Winchester Vacation Rentals with a Pool

Pet-Friendly Vacation Rentals in Winchester

Over 64+ Pet-Friendly Vacation Rentals in or Near Winchester
Lake, Caverns, Sewanee, & Jack Daniel’s All Nearby! Boat, RV, Camping, Barn From US $374
         

10.0 (13 Reviews)
House
Lake, Caverns, Sewanee, & Jack Daniel’s All Nearby! Boat, RV, Camping, Barn
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Beautifully Renovated Studio 2 Miles From Marina! From US $121
         

|
9.6 (11 Reviews)
Apartment
Beautifully Renovated Studio 2 Miles From Marina!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Enjoy fireside sunset & walk to movies, shops, restaurants! From US $322
         

10.0 (81 Reviews)
House
Enjoy fireside sunset & walk to movies, shops, restaurants!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family From US $685
         

10.0 (35 Reviews)
House
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Lake View Prime Location, Community Dock w swim ladders, covered boat slip, From US $698
         

10.0 (23 Reviews)
House
Lake View Prime Location, Community Dock w swim ladders, covered boat slip,
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Basecamp Retreat TimsFordLake From US $254
         

10.0 (12 Reviews)
House
Basecamp Retreat TimsFordLake
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Spacious Lakeside Home, Pet-Friendly w/Dock & Boatslip From US $413
         

10.0 (11 Reviews)
House
Spacious Lakeside Home, Pet-Friendly w/Dock & Boatslip
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Twin Creeks Getaway- Pet Friendly- Amenities Abound! Golf cart rental available! From US $279
         

10.0 (6 Reviews)
House
Twin Creeks Getaway- Pet Friendly- Amenities Abound! Golf cart rental available!
  • Air Conditioner
  • Pet Friendly
  • Pool

View Availability
See More Pet-Friendly Vacation Rentals in Winchester on PetFriendly.io

Large Vacation Homes & Villas in Winchester

Over 130+ Large Vacation Homes & Villas in or Near Winchester
Hickory Hideaway on Tim`s Ford Lake, Boat rental available From US $497
         

10.0 (90 Reviews)
House
Hickory Hideaway on Tim`s Ford Lake, Boat rental available
  • Air Conditioner
  • Parking
  • TV

View Availability
Lake Home Retreat w/Lake/Marina Access Golf Cart From US $380
         

|
10.0 (2 Reviews)
House
Lake Home Retreat w/Lake/Marina Access Golf Cart
  • Air Conditioner
  • Parking
  • Pool

View Availability
Million Dollar Views + Luxury + Infinity Deck From US $672
         

10.0 (52 Reviews)
House
Million Dollar Views + Luxury + Infinity Deck
  • Air Conditioner
  • Parking
  • TV

View Availability
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks From US $239
         

10.0 (49 Reviews)
House
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks
  • Air Conditioner
  • Parking
  • TV

View Availability
A Little Slice of Heaven - Come see one of Tennessee's best kept secrets From US $675
         

10.0 (41 Reviews)
House
A Little Slice of Heaven - Come see one of Tennessee's best kept secrets
  • Air Conditioner
  • Parking
  • TV

View Availability
Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart From US $223
         

10.0 (32 Reviews)
House
Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart
  • Air Conditioner
  • Parking
  • TV

View Availability
Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc From US $208
         

10.0 (31 Reviews)
House
Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc
  • Air Conditioner
  • Parking
  • TV

View Availability
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK From US $468
         

10.0 (26 Reviews)
House
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
  • Air Conditioner
  • Parking
  • TV

View Availability
See More Family Vacation Rentals in Winchester on FVR

Wheelchair Accessible Vacation Homes in Winchester

Over 3+ Wheelchair Accessible Vacation Homes in or Near Winchester
Luxury Estate Center of Tims Ford Lake with Unbeatable Lakefront Views, Dock From US $1,274
         

10.0 (44 Reviews)
House
Luxury Estate Center of Tims Ford Lake with Unbeatable Lakefront Views, Dock
  • Air Conditioner
  • Parking
  • TV

View Availability
Best Western Inn Winchester From US $146
         

|
7.6 (125 Reviews)
Hotel
Best Western Inn Winchester
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
NEW!!! Lake Life Retreat with all the top amenities From US $652
         

5.0 (12 Reviews)
House
NEW!!! Lake Life Retreat with all the top amenities
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace

View Availability
See More Properties

Winchester Varoom and Airbnb Places to Stay Under $200

Over 54+ Winchester Varoom and Airbnb Places to Stay Under $200
Barefoot Retreat w/kayaks/SUP/fireplace/Community Pool From US $179
         

10.0 (20 Reviews)
House
Barefoot Retreat w/kayaks/SUP/fireplace/Community Pool
  • Air Conditioner
  • Parking
  • TV

View Availability
Gorgeous Renovated Home With Large & Private Lot From US $200
         

|
6.8 (11 Reviews)
House
Gorgeous Renovated Home With Large & Private Lot
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Best Western Inn From US $111
         

8.8 (669 Reviews)
Hotel
Best Western Inn
  • Air Conditioner
  • Parking
  • Pool

View Availability
Historic 1940's Cottage Near Tim's Ford Lake & Town Square Fully Remodeled From US $155
         

10.0 (8 Reviews)
Cottage
Historic 1940's Cottage Near Tim's Ford Lake & Town Square Fully Remodeled
  • Air Conditioner
  • Parking
  • TV

View Availability
Lakin It Easy-Pool, Twin Creeks Marina, & Dry Creek Beach From US $195
         

10.0 (6 Reviews)
House
Lakin It Easy-Pool, Twin Creeks Marina, & Dry Creek Beach
  • Air Conditioner
  • Parking
  • Pool

View Availability
Lovin Lake Life-Pool, Twin Creeks Marina, & Dry Creek Beach From US $199
         

10.0 (1 Review)
Villa
Lovin Lake Life-Pool, Twin Creeks Marina, & Dry Creek Beach
  • Air Conditioner
  • Parking
  • Pool

View Availability
Cozy Lake Cottage W/Pool, Hot Tub,Kayaks, SUPs From US $166
         

9.8 (17 Reviews)
House
Cozy Lake Cottage W/Pool, Hot Tub,Kayaks, SUPs
  • Air Conditioner
  • Parking
  • Pool

View Availability
Oasis on the Square From US $143
         

9.8 (11 Reviews)
Apartment
Oasis on the Square
  • Air Conditioner
  • Parking
  • TV

View Availability
See More Winchester Vacation Rental Deals

Instantly Bookable Vacation Homes in Winchester

Over 130+ Instantly Bookable Vacation Homes in or Near Winchester
Private dock/gazebo on quiet cove. Tims Ford Lake! From US $352
         

10.0 (39 Reviews)
House
Private dock/gazebo on quiet cove. Tims Ford Lake!
  • Air Conditioner
  • Parking
  • TV

View Availability
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort From US $789
         

10.0 (8 Reviews)
House
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
  • Air Conditioner
  • Parking
  • TV

View Availability
Family friendly lake front home with private dock in a cove From US $499
         

10.0 (25 Reviews)
House
Family friendly lake front home with private dock in a cove
  • Air Conditioner
  • Parking
  • TV

View Availability
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC From US $185
         

New
House
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC
  • Air Conditioner
  • Parking
  • TV

View Availability
Dock, Water Views, Kayaks, Fire Pit, Game Room From US $231
         

10.0 (25 Reviews)
House
Dock, Water Views, Kayaks, Fire Pit, Game Room
  • Air Conditioner
  • Parking
  • TV

View Availability
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks From US $214
         

10.0 (25 Reviews)
Cabin
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks
  • Air Conditioner
  • TV
  • View

View Availability
Lakeshore Modern! Lake front with platform dock and 2 kayaks, firepit and views From US $532
         

10.0 (24 Reviews)
House
Lakeshore Modern! Lake front with platform dock and 2 kayaks, firepit and views
  • Air Conditioner
  • Parking
  • TV

View Availability
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak From US $409
         

10.0 (21 Reviews)
House
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak
  • Air Conditioner
  • Parking
  • TV

View Availability
See More Winchester Short-Term Vacation Rentals

About Winchester Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Lakesresorts Winchester, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Winchester. Places to stay near Winchester are 7997.59 ft² on average, with prices averaging $1,978 a night.

Lakesresorts makes it easy and safe to find and compare vacation rentals in Winchester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Winchester

Type Count
Vacation Homes 1

Use these Quick Filters to Find a Vacation Rental in Winchester

★ Pro Tip: Lakesresorts makes it easy to compare the best listings on Lakesresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Lakesresorts homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winchester.

Weather in Winchester

View the weather forecast for Winchester before booking your Winchester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Winchester, TN

Lakesresorts offers a large selection of top attractions around Winchester. Research things to do on your vacation before you visit Winchester.


Tims Ford State Park Tims Ford Lake Tim's Ford Marina Hammers Expressions Jack Daniel's Distillery Great Stage Park Bonnaroo Music & Arts Festival University of the South Guntersville Lake Monteagle Sunday School Assembly Foster Falls South Cumberland State Park Calsonic Arena Lynchburg Hardware and General Store Shelbyville Recreation Center George Dickel Distillery Tennessee Walking Horse National Museum Elk River Dam Sewanee Golf and Tennis Club

Other Places to Stay Near Winchester, TN


Franklin County 240 Properties Expressions 160 Properties Hammers 160 Properties Tim's Ford Marina 137 Properties Tims Ford State Park 103 Properties Tims Ford Lake 73 Properties

Complexes around Winchester, TN


Townhouse At Creeks Resort Marina 2 Properties