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 3.309.491 ₫ per night from 27 Jun to 28 Jun
3.309.491 ₫
3.781.094 ₫ total
27 Jun - 28 Jun
includes taxes & fees
8.6/10 Excellent! (611 reviews)
"Very nice room with hot tub. Perfect stay, cannot complain about anything"

Reviewed on 17 Jun 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 1.463.075 ₫ per night from 25 Jun to 26 Jun
1.463.075 ₫
1.678.917 ₫ total
25 Jun - 26 Jun
includes taxes & fees
8.4/10 Very Good! (1,112 reviews)
"Cool hang out areas on the property. Rooms are ok, but clean!"

Reviewed on 22 Jun 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 1.776.908 ₫ per night from 1 Jul to 2 Jul
1.776.908 ₫
2.101.194 ₫ total
1 Jul - 2 Jul
includes taxes & fees
8.6/10 Excellent! (793 reviews)
"We had a handicap room which I felt weird having since I didn’t need that type of accommodation. It was difficult to shower as there was no shower head attached to the wall, just a hose with an attachment just hanging down. You could hear almost everything as the rooms are not very well insulated. ..."

Reviewed on 21 Jun 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.

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.

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