Winchester Holidays from AU$1,974

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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.
Sonesta Nashville Airport

Sonesta Nashville Airport

4 out of 5
per person
29 Oct - 5 Nov
found 1 day ago
Return direct flight included
Melbourne (MEL) to Nashville (BNA)
9/10 Wonderful! (1,677 reviews)
Nice property. Clean and in a good area distance wise. Only major issue is parking. It’s $20 a day to self park… other than that, I would stay again.

Reviewed on 5 Aug. 2025

Bobby Hotel

Bobby Hotel

4 out of 5
Downtown Nashville
Save 100% on your flight
per person
29 Oct - 5 Nov
found 1 day ago
Return direct flight included
Melbourne (MEL) to Nashville (BNA)
9.4/10 Exceptional! (1,001 reviews)
Nice lobby, nice room, nice rooftop restaurant and pool. Convenient location right next to Printers Alley & 10 min walk to Broadway. Nice 4 star hotel.

Reviewed on 6 Aug. 2025

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
per person
29 Oct - 5 Nov
found 1 day ago
Return direct flight included
Melbourne (MEL) to Nashville (BNA)
9.2/10 Wonderful! (818 reviews)
I didnt feel like the hotel was as clean as you would expect. Dirt and dust noticed in the corners or room and elevator. I know that sounds picky but for a hotel with a great reputation I would expect better.

Reviewed on 2 Aug. 2025

Sentral Sobro

Sentral Sobro

4 out of 5
Downtown Nashville
per person
29 Oct - 5 Nov
found 1 day ago
Return direct flight included
Melbourne (MEL) to Nashville (BNA)
8.8/10 Excellent! (1,480 reviews)
Walking distance to broadway with great food options along the way Rooms were clean and the bed was comfy Amenities were also clean

Reviewed on 3 Aug. 2025

Fairlane Hotel

Fairlane Hotel

4 out of 5
Downtown Nashville
per person
29 Oct - 5 Nov
found 1 day ago
Return direct flight included
Melbourne (MEL) to Nashville (BNA)
9.4/10 Exceptional! (1,000 reviews)
Very friendly staff, welcoming, good central location.

Reviewed on 4 Aug. 2025

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$208 per night from 19 Aug to 20 Aug
AU$208
19 Aug - 20 Aug
includes taxes & fees
8.6/10 Excellent! (619 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! (8 reviews)
Perfect getaway
"We loved everything about our stay. The place was clean and well stocked. The dock was perfect for fishing (we brought our own gear). The Kayaks and floating Lilly Pad provided hours of entertainment. The hot tub was clean. A large dining table for meals and games. Living room had lots of comfortable ..."

Reviewed on 1 Aug. 2025

Get rates
Reflection Bay-Dock, Hot Tub, Kayaks
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

Winchester
10/10 Exceptional! (46 reviews)
Family Vacation
"Our granddaughters loved the dock! Peaceful beautiful setting."

Reviewed on 2 Jul. 2025

Get rates
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks
See all 657 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$1,974 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.