Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

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 2.897.940 ₫ per night from 27 Aug to 28 Aug
2.897.940 ₫
3.310.897 ₫ total
27 Aug - 28 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
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 1.475.784 ₫ per night from 23 Sept to 24 Sept
1.475.784 ₫
1.693.501 ₫ total
23 Sept - 24 Sept
includes taxes & fees
8.4/10 Very Good! (1,127 reviews)
"We went to dinner at their restaurant. Our server was very nice, but the food took forever. Everyone that came in after us was served promptly, when our server came to us to apololgize she said the cook was taking orders out of order. We still waited and finally had to go up to the desk, were told ..."

Reviewed on 21 Aug 2025

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 1.662.384 ₫ per night from 24 Aug to 25 Aug
1.662.384 ₫
1.965.770 ₫ total
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (880 reviews)
"Loved my stay"

Reviewed on 19 Aug 2025

Microtel Inn & Suites by Wyndham Manchester
See all 651 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.

Popular places to visit

Hammers

Enjoy an outing to Hammers during your stay in Winchester. Stroll along the lakeside or discover the area's mountain views.

Hammers

Expressions

Enjoy an outing to Expressions during your stay in Winchester. Amble around the area's lakeside or experience its musical theatre.

Expressions

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.