Winchester holiday homes

We found 269 holiday rentals — enter your dates for availability
Select from 113 homes, 10 cottages and other holiday rentals in Winchester to find one that's perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you expect for your stay, which might include parking and a pool. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Winchester

Showing deals for:18 Dec - 25 Dec

Private kitchen
Dining
Terrace/patio
Marina
Exceptional
(33 reviews)

Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK

Winchester

8% off
NZ$8,879
for 7 nights, 1 home
NZ$1,268 per night
includes taxes & fees
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
Interior
Private kitchen
Property grounds
Exterior
Exceptional
(10 reviews)

Majestic Lakehouse -Hot Tub-Private Boat Dock- 5 bedrooms, Pool Table, Ping Pong

Estill Springs

7% off
NZ$11,075
for 7 nights, 1 home
NZ$1,582 per night
includes taxes & fees
Majestic Lakehouse -Hot Tub-Private Boat Dock- 5 bedrooms, Pool Table, Ping Pong
Games room
Property grounds
Living area
Room
Exceptional
(17 reviews)

“Family Traditions” Cottage - 4-bed lake retreat

Tullahoma

7% off
NZ$5,554
for 7 nights, 1 home
NZ$793 per night
includes taxes & fees
“Family Traditions” Cottage - 4-bed lake retreat
Private kitchen
Living area
Terrace/patio
Dining
Exceptional
(32 reviews)

Lakeshore Modern! Lake front with platform dock and 2 kayaks, firepit and views

Winchester

7% off
NZ$9,655
for 7 nights, 1 home
NZ$1,379 per night
includes taxes & fees
Lakeshore Modern! Lake front with platform dock and 2 kayaks, firepit and views
Exterior
Property grounds
Dining
Property grounds
Exceptional
(23 reviews)

“License To Chill”. Lake Cottage at Tims Ford Lake Golf cart/Fire pit/Marina

Tullahoma

7% off
NZ$4,166
for 7 nights, 1 cottage
NZ$595 per night
includes taxes & fees
“License To Chill”. Lake Cottage at Tims Ford Lake Golf cart/Fire pit/Marina
Exterior
Property grounds
Living area
Private kitchen
Exceptional
(16 reviews)

A-Frame on Tims Ford Lake Private Boat Dock

Tullahoma

7% off
NZ$3,200
for 7 nights, 1 cabin
NZ$457 per night
includes taxes & fees
A-Frame on Tims Ford Lake Private Boat Dock
Living area with TV and plenty of games!
Exterior
Screened in back porch.
Bright, clean kitchen has all of the amenities of home.
Exceptional
(12 reviews)

Salsa Lido@Twin Creeks Resort, The lake is calling

Winchester

7% off
NZ$7,498
for 7 nights, 1 home
NZ$1,071 per night
includes taxes & fees
Salsa Lido@Twin Creeks Resort, The lake is calling
Twin Creeks Marina
Twin Creeks - sunset
Street view 1
Dock viewed from house rear deck
Exceptional
(61 reviews)

'Tennessee Tahoe': Tims Ford Lake - Cozy Cabin with Two Level Dock

Estill Springs

8% off
NZ$4,957
for 7 nights, 1 home
NZ$708 per night
includes taxes & fees
'Tennessee Tahoe': Tims Ford Lake - Cozy Cabin with Two Level Dock
Dining room with large table that seats 8
Kitchen looking into living room
Kitchen with large island (seating for 4)
Covered patio (new gas grill and family swing not pictured)
Exceptional
(20 reviews)

Tims Ford Lake Home! Walk to marina, pool table, firepit, 2 kings + bunks 3Baths

Tullahoma

7% off
NZ$3,828
for 7 nights, 1 home
NZ$547 per night
includes taxes & fees
Tims Ford Lake Home! Walk to marina, pool table, firepit, 2 kings + bunks 3Baths
Room
Living area
Terrace/patio
Bathroom
Exceptional
(37 reviews)

Charming cottage in wooded location

Sewanee

24% off
NZ$2,364
for 7 nights, 1 cottage
NZ$338 per night
includes taxes & fees
Charming cottage in wooded location
Exterior
Terrace/patio
Property grounds
Terrace/patio
Exceptional
(33 reviews)

Lake Life 4 Bedroom, 3 Bath, Sleeps 12.

Estill Springs

7% off
NZ$6,479
for 7 nights, 1 home
NZ$926 per night
includes taxes & fees
Lake Life 4 Bedroom, 3 Bath, Sleeps 12.
Room
Marina
Interior
Exterior
Exceptional
(5 reviews)

Whiskey Woods Retreat! The ultimate escape!

Tullahoma

15% off
NZ$1,710
for 7 nights, 1 home
NZ$244 per night
includes taxes & fees
Whiskey Woods Retreat! The ultimate escape!
Room
Lobby
Front lobby with staircase
Exterior front of Franklin House in Cowan
Exceptional
(13 reviews)

Cozy king ensuite room in historic railroad inn

Cowan

20% off
NZ$2,145
for 7 nights, 1 room
NZ$306 per night
includes taxes & fees
Cozy king ensuite room in historic railroad inn
Living area
Terrace/patio
Room
Interior
Exceptional
(19 reviews)

Cabin in Country close to Lake w Hot Tub.

Tullahoma

11% off
NZ$2,001
for 7 nights, 1 home
NZ$286 per night
includes taxes & fees
Cabin in Country close to Lake w Hot Tub.
Interior
Interior
Room
Interior detail
Exceptional
(14 reviews)

Nostalgic Q ensuite room in historic railroad inn.

Cowan

20% off
NZ$1,896
for 7 nights, 1 room
NZ$271 per night
includes taxes & fees
Nostalgic Q ensuite room in historic railroad inn.

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Travel to charming Winchester

The lake and other outdoor surroundings create an inviting atmosphere in Winchester. Travellers especially like the theme park, boating and university setting in this romantic and welcoming city. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Winchester

Do you want to discover attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winchester a fun spot to go on holiday. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Tim's Ford Marina (7.9 mi / 12.7 km)
  • Hammers (0.1 mi / 0.1 km)
  • Bear Trace Golf Course (8.5 mi / 13.7 km)
  • Sewanee Golf and Tennis Club (11.3 mi / 18.2 km)
  • Arnold Golf Course (12.1 mi / 19.4 km)
  • Lakewood Golf & Country Club (15.1 mi / 24.3 km)

Exploring the natural landscape of Winchester

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Winchester is a great place to spend some time outside. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Tims Ford Lake (9.4 mi / 15.1 km)
  • Lake Cheston (10.3 mi / 16.7 km)
  • Walls of Jericho Hiking Trailhead (14.6 mi / 23.4 km)
  • Rutledge Falls (16.4 mi / 26.3 km)
  • The Caverns (19.1 mi / 30.7 km)
  • Great Stage Park (20 mi / 32.3 km)

Travelling to and around Winchester

The nearest airport is in Chattanooga, TN (CHA-Chattanooga Metropolitan), located 52.8 mi (85 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Huntsville International Airport (HSV), which is 52.8 mi (85 km) away.

Frequently asked questions

What is the best area to stay in Winchester when booking a holiday rental?
When considering a holiday rental in Winchester, Tennessee, the downtown area is an excellent choice. This vibrant neighbourhood offers a charming small-town atmosphere with a variety of local shops, restaurants, and cafes that reflect the community's welcoming spirit. One of the highlights of staying in this area is the beautiful Tims Ford Lake, which is superb for outdoor enthusiasts looking to enjoy activities such as fishing, boating, or simply relaxing by the water. Additionally, the nearby Old Jail Museum provides a fascinating glimpse into local history and is a great spot for those interested in heritage and culture.Another noteworthy option is the area around the Winchester Golf Club, which not only attracts golf enthusiasts but also offers stunning views and a serene environment. This part of Winchester is surrounded by lush greenery and is superb for leisurely walks or picnics. With a range of properties available, from charming cottages to spacious family homes, visitors can find accommodations that suit their needs while enjoying the best that Winchester has to offer.
What is the most popular type of holiday rental accomodation in Winchester?
In Winchester, holiday houses are the most popular type of holiday rental, with around 380 available throughout the area. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor areas great for relaxation. Many are located in serene neighbourhoods, allowing guests to enjoy the peaceful surroundings. Additionally, there are about 72 cabins, which offer a rustic charm and often include amenities like fireplaces and nature views, ideal for a cozy getaway. For those seeking a more quaint experience, around 40 cottages are also available, providing a charming and homely feel. Apartments, while less common, number about 32 and generally include essential amenities for a comfortable stay.
Are there any family house rentals in Winchester?
In Winchester, Tennessee, there are numerous family-friendly house rentals available, with around 99 options to choose from. This charming town offers a variety of properties, often featuring spacious living areas, full kitchens great for preparing family meals, and comfortable outdoor spaces for children to enjoy. Many homes also come equipped with essential amenities such as Wi-Fi and air conditioning, ensuring a pleasant stay for visitors.The local area provides opportunities for exploration, with nearby attractions including the scenic Tims Ford Lake, ideal for boating and fishing, and the picturesque Tims Ford State Park, which offers hiking trails and picnic spots for those keen on outdoor activities. Additionally, the vibrant downtown area of Winchester is home to quaint shops and restaurants, making it a delightful place for families to experience local culture.
Can I rent a holiday home with a pool or hot tub in Winchester?
In Winchester, Tennessee, there are a variety of holiday homes available for rent that feature pools and hot tubs, with around 39 options to choose from. This charming town is located between scenic lakes and rolling hills, making it an inviting destination for travellers seeking relaxation and outdoor activities.Many of the available properties come with amenities such as private pools, hot tubs, and spacious outdoor areas great for gatherings or family fun. Inside, you can expect fully equipped kitchens, comfortable living spaces, and often multiple bedrooms, suiting groups or families.
Are there pet-friendly house rentals in Winchester?
In Winchester, there are several pet-friendly house rentals available, with around 37 options to choose from. Many of these properties come equipped with amenities that cater to both human and furry guests, including spacious outdoor areas for pets to roam, fully equipped kitchens for home-cooked meals, and comfortable living spaces for relaxation.The town features a number of parks and green spaces, such as the beautiful Tims Ford State Park, where visitors can enjoy hiking trails, picnic areas, and opportunities for fishing and boating, making it a great spot for those travelling with pets. Additionally, the surrounding areas offer scenic views and a tranquil atmosphere, ideal for a peaceful getaway with your four-legged companions.
Are there any remote work holiday rentals in Winchester?
In Winchester, Tennessee, there are a significant number of remote work-friendly holiday rentals available, with around 496 options to choose from. Many of these accommodations cater specifically to the needs of remote workers, offering amenities such as complimentary Wi-Fi in both rooms and public areas, dedicated desks, and comfortable laptop workspaces.Travellers can expect a range of properties, from cosy apartments to spacious houses, often featuring modern conveniences like fully equipped kitchens, laundry facilities, and outdoor spaces for relaxation. The town is known for its charming atmosphere and proximity to local attractions, including parks and lakes, which can provide a nice break from work. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Winchester?
In Winchester, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature onsite parking for convenience, as well as decks or patios where travellers can enjoy the pleasant outdoors. A fireplace is a common amenity, providing a cosy atmosphere during cooler evenings, while a coffee and tea maker is typically available for those who enjoy a warm beverage.
When is the best time to visit Winchester for a holiday rental?
The peak season for visiting Winchester, Tennessee, runs from May to July, making it an ideal time for travellers seeking a vibrant holiday experience. With the warm weather and a plethora of outdoor activities, this period attracts travellers, ready to explore the natural beauty and rich history of the area.July stands out as the most popular month, offering visitors the chance to engage in various outdoor pursuits, such as hiking in the nearby Tims Ford State Park or enjoying leisurely picnics by the lake. The pleasant temperatures, typically ranging from 20 to 32 degrees Celsius, create a comfortable environment for sightseeing and enjoying local events.If you're looking for a more budget-friendly option, consider planning your trip in November. This month sees fewer tourists, allowing for a more tranquil experience while still providing the opportunity to explore Winchester's charming downtown and surrounding landscapes in a quieter setting.
What are the top attractions in Winchester?
In Winchester, Tennessee, visitors can enjoy a variety of attractions that showcase the area's natural beauty and historical significance. One of the main highlights is the scenic Tims Ford Lake, where outdoor enthusiasts can partake in fishing, boating, and hiking along the picturesque trails. The nearby Tims Ford State Park offers camping facilities and picnic areas, making it an ideal spot for families and nature lovers.The downtown area features charming shops and local eateries, providing a quaint atmosphere to explore. Additionally, the Winchester City Park is a lovely place for leisurely walks and enjoying community events throughout the year. For history buffs, the Old Jail Museum offers insights into the local history and is a fascinating stop.
Are all fees included in the Winchester holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Winchester holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Winchester with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Winchester holiday homes?
You can find great discounts on holiday homes in Winchester on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Winchester holiday home booking on Bookabach?
To find Winchester holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Winchester?
A long-stay holiday home in Winchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winchester holiday home?
Book your Winchester holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winchester?
Prices for holiday homes in Winchester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Winchester to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.