Winchester Holidays

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Top hotels in Winchester

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 Rp1.781.930 per night from 9 Jul to 10 Jul
Rp1.781.930
Rp2.035.747 total
9 Jul - 10 Jul
includes taxes & fees
8.8/10 Excellent! (726 reviews)
"Cozy spot"

Reviewed on 6 Jul 2026

Best Western Inn
The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

3 out of 5
844 W Main Street Monteagle TN
Fully refundableReserve now, pay when you stay
The price is Rp1.005.748 per night from 9 Jul to 10 Jul
Rp1.005.748
Rp1.154.123 total
9 Jul - 10 Jul
includes taxes & fees
8.6/10 Excellent! (1,216 reviews)
"The cabins are very cute; however, ours was not clean. There was mildew all along the baseboards. We bought Clorox wipes and cleaned it. A little work on these and they would be a great place to stay."

Reviewed on 5 Jul 2026

The Smokehouse Lodge and Cabins
Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

2 out of 5
201 Expressway Dr Manchester TN
Fully refundableReserve now, pay when you stay
The price is Rp1.129.873 per night from 22 Jul to 23 Jul
Rp1.129.873
Rp1.336.075 total
22 Jul - 23 Jul
includes taxes & fees
8.8/10 Excellent! (1,108 reviews)
"They were clean and cozy , the pool Was a little dirty but other then that it was very clean , very friendly"

Reviewed on 5 Jul 2026

Microtel Inn & Suites by Wyndham Manchester
See all 795 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.

Stay near popular Winchester attractions

Bear Trace Golf Course

Jack Nicklaus designed this lakeside golf course to harmonise with Tennessee's natural landscape. Enjoy strategic play across 18 holes with panoramic views of Tims Ford Lake and pristine fairways.
See properties

Frequently asked questions

How much does a Winchester holiday package cost?
You'll find cheap prices 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.

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