Winchester Holidays from AU$2,659

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Your Winchester Holiday

There's no better way to escape than with one of our holiday packages to Winchester. The rich history and spectacular views are among the countless reasons to stay in this interesting city. Your trip to Winchester wouldn't be complete without swinging by a few leading attractions, such as Hammers. Your dream Winchester holiday is just a few clicks away. Browse hotels, flights and more on Expedia for a getaway that's tailored just for you.

The Latest Winchester Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Nashville West End Avenue

Hilton Garden Inn Nashville West End Avenue

3 out of 5
West End
Price was AU$3,237, price is now AU$2,659 per person
AU$2,659
per person
29 Oct - 5 Nov
found 1 day ago
Return direct flight included
Melbourne (MEL) to Nashville (BNA)
9.2/10 Wonderful! (317 reviews)
Our stay was very comfortable and pleasant. We loved the location of the hotel, the cleanliness, and the layout of the room. We also enjoyed the convenience of the restaurant being available for breakfast, lunch, and dinner. We'll definitely be back.

Reviewed on 15 Aug. 2025

East Nash Lux - 13 Beds City Views

East Nash Lux - 13 Beds City Views

2 out of 5
East Nashville
Price was AU$3,788, price is now AU$3,248 per person
AU$3,248
per person
29 Oct - 5 Nov
found 1 day ago
Return direct flight included
Melbourne (MEL) to Nashville (BNA)
No reviews
The Westin Nashville

The Westin Nashville

4 out of 5
Downtown Nashville
Price was AU$3,512, price is now AU$3,239 per person
AU$3,239
per person
29 Oct - 5 Nov
found 1 day ago
Return direct flight included
Melbourne (MEL) to Nashville (BNA)
8.6/10 Excellent! (1,000 reviews)
It was easy to walk to places.

Reviewed on 17 Aug. 2025

New Build Sleeps 12, 2 Condos in Scenic Bluffside, Minutes to Downtown

New Build Sleeps 12, 2 Condos in Scenic Bluffside, Minutes to Downtown

3 out of 5
Bordeaux
Price was AU$3,852, price is now AU$3,569 per person
AU$3,569
per person
29 Oct - 5 Nov
found 1 day ago
Return direct flight included
Melbourne (MEL) to Nashville (BNA)
No reviews
New Build Sleeps 12, 2 Condos, Modern Design Near Downtown Nashville

New Build Sleeps 12, 2 Condos, Modern Design Near Downtown Nashville

3 out of 5
Bordeaux
Price was AU$3,852, price is now AU$3,569 per person
AU$3,569
per person
29 Oct - 5 Nov
found 1 day ago
Return direct flight included
Melbourne (MEL) to Nashville (BNA)
No reviews

Winchester Holiday

Winchester Essential Information

Language
English
Currency
U.S dollars
Population
8,500
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Tims Ford State Park, University of the South and Tims Ford Lake

Our pick of the best Winchester Hotel Deals

Best Western Inn

Best Western Inn

2.5 out of 5
1602 Dinah Shore Boulevard, Winchester, TN
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 23 Aug to 24 Aug
AU$193
23 Aug - 24 Aug
includes taxes & fees
8.6/10 Excellent! (620 reviews)
"Room was clean, staff were very kind and helpful. Property was quiet and well maintained. My only two minor gripes are that the coffee machine was broken both days, and there was what appeared to be mold on the bathroom ceiling. Those were small things, overall I enjoyed my stay."

Reviewed on 25 Jul. 2025

Best Western Inn
Reflection Bay-Dock, Hot Tub, Kayaks

Reflection Bay-Dock, Hot Tub, Kayaks

Winchester
10/10 Exceptional! (9 reviews)
"Communication was excellent!"

Reviewed on 17 Aug. 2025

Get rates
Reflection Bay-Dock, Hot Tub, Kayaks
Spacious Lakefront Retreat w/ Hot Tub + Dock!

Spacious Lakefront Retreat w/ Hot Tub + Dock!

Winchester
9.8/10 Exceptional! (22 reviews)
Retirement celebration
"Beautiful home. Living area and kitchen were large enough to accommodate our large family"

Reviewed on 30 Jun. 2025

Get rates
Spacious Lakefront Retreat w/ Hot Tub + Dock!
See all 652 properties in Winchester
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Winchester

Tim's Ford Marina

Bring the family to Tim's Ford Marina and enjoy the excitement of this theme park in Winchester. Discover the countryside while you're in the area.

Tim's Ford Marina

Frequently asked questions

How much does a Winchester holiday package cost?
You'll find cheap prices from AU$2,659 on Expedia for your Winchester escape. However, factors like your choice of hotel, the season and length of stay will determine how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
December, January and February are the best times to look for cheap Winchester holiday packages. Travelling in less busy months means you can generally find better prices on flights and accommodation.
How many days is enough for Winchester?
With a well-planned schedule, you can easily tick off the main Winchester sights in a few days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Winchester holiday for longer.
How to find the best Winchester package deals?
Finding a cheap Winchester package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Winchester package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can tailor your Winchester trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Winchester?
Enjoy amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Winchester holiday.
How to plan a trip to Winchester?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Winchester.
  2. Set your budget: Factor in costs like transportation, flights and meals when calculating how much to put aside for your trip to Winchester. Then, select a property that suits your budget, whether that's an economical stay or a deluxe getaway.
  3. Decide how long to go for: Now that you know more about Winchester, you can work out the ideal length of your break. Pull together a rough plan and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalised Winchester holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.