Winchester Vacations from $570

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Your Winchester Vacation

The rich history and spectacular views are just the start of the things Winchester has on offer. Experience the very best of this interesting city your way with a tailor-made Winchester vacation package. Any trip to Winchester should include some sightseeing. Hammers is a great place to kick things off. Whoever you're going away with and whatever you want to spend, your dream Winchester vacation is just a few clicks away with Expedia.

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Club Wyndham Nashville
Bobby Hotel
Waymore's Guest House & Casual Club
Fiddler's Inn
Mint House at The Reserve - Nashville
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Discover the most popular places to visit in Winchester

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
$110 nightly
The price is $125 total per night from Aug 26 to Aug 27
$125 total
Aug 26 - Aug 27
Total with taxes and 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 Jul 25, 2025

Best Western Inn
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 Jun 30, 2025

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

Reflection Bay-Dock, Hot Tub, Kayaks

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

Reviewed on Aug 17, 2025

Reflection Bay-Dock, Hot Tub, Kayaks
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.

Things to do in and around Winchester

Winchester, Tennessee, is perfect for outdoor enthusiasts and romantic getaways, offering a range of activities like hiking trails, campgrounds, and recreational areas. Don't miss the chance to explore local tour options, enjoy seasonal events like the Halloween haunt, and take part in mansion tours. Art celebrations and the enchanting Story Land add to the charm, making Winchester a delightful destination for visitors seeking adventure and culture.

Shopping

In Winchester, visit Hammers for a unique shopping experience filled with various gifts. If you're up for a drive, head to Northgate Mall in Tullahoma, 15 miles away, for entertainment and family-friendly vibes, or check out Lynchburg Hardware and General Store, located 16 miles from Winchester.

Recreation

At Sewanee Golf and Tennis Club, enjoy a round of golf surrounded by beautiful landscapes, perfect for relaxation and sport enthusiasts. Hank Weddington Park offers a family-friendly playground, ideal for outdoor fun. The City of Decherd Babe Ruth Ball Park provides a serene environment for wellness and relaxation activities.

Adventure

Experience the thrill of soaring through the trees at Bigfoot Adventure TN Zipline, located 21 miles from Winchester. Enjoy the stunning views while navigating the Estill Springs Walking Trail, a scenic hike only 6 miles away, or challenge yourself on the Walls of Jericho Hiking Trailhead, 15 miles from town.

Nightlife

In Winchester, Tennessee, enjoy a relaxed nightlife atmosphere with local bars and music venues. Check out the lively scenes at the community center or nearby pubs, where you can unwind with friends, enjoy live performances, and savor regional brews in a friendly, welcoming environment.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Winchester

Winchester, Tennessee, is an ideal destination for outdoor and romantic vacations, offering scenic spots like islands, marinas, and marine parks. Visitors can enjoy family-friendly experiences while exploring attractions such as the intriguing Winchester Mystery House and its associated packages. This charming town combines natural beauty with unique sites, making it perfect for travelers seeking adventure and a touch of the bizarre in their getaway.

  • Tim's Ford Marina: Experience the ultimate outdoor adventure at Tim's Ford Marina, where you can enjoy boating, fishing, and swimming in the beautiful waters. With its beach vibes, it’s a perfect spot for relaxation and fun in the sun, offering scenic views and a welcoming atmosphere.
  • Expressions: Embrace the romantic vibes at Expressions, where art and creativity come together. This charming attraction offers a unique experience through its captivating exhibits, making it an ideal spot for couples seeking inspiration and intimacy in a picturesque setting.
  • Elk River Dam: Located 8 miles away, Elk River Dam provides breathtaking lookout points for nature enthusiasts. Enjoy outdoor activities while soaking in the stunning views, making it a perfect blend of adventure and romance for your getaway.

Best time to go to Winchester

The best time to visit Winchester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winchester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winchester falls in January, visitor numbers are average and weather is mostly with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January38.3°F (3.5°C)Light RainMostlyAverageSlightly Low
February42.8°F (6.0°C)Light RainMostlyAverageSlightly Low
March50.4°F (10.2°C)Light RainMostly SunnyAverageAverage
April57.9°F (14.4°C)Light RainMostly SunnySlightly HighAverage
May66.7°F (19.3°C)Light RainMostly SunnyAverageSlightly High
June74.5°F (23.6°C)Light RainMostly SunnySlightly HighSlightly High
July76.8°F (24.9°C)Light RainMostly SunnySlightly HighAverage
August75.6°F (24.2°C)Light RainMostly SunnyAverageAverage
September70.5°F (21.4°C)Light RainMostly SunnyAverageAverage
October59.9°F (15.5°C)Light RainMostly SunnySlightly LowSlightly High
November48.9°F (9.4°C)Light RainMostly SunnySlightly LowAverage
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowSlightly Low

Tips to save on your trip to Winchester

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Winchester.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Winchester.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $570 on Expedia for your Winchester escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
If you'd like to book a cheap Winchester vacation package, consider planning a trip in October, November and December. You'll typically find better prices on hotels and airfares during these quieter months — perfect for a budget-friendly break.
How many days is enough for Winchester?
The ideal length of your Winchester vacation depends on what you'd like to do and see. Usually, a few days to a week will give you plenty of time to hit all the main sights and explore some hidden gems along the way.
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 traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation 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 vacation 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 vacation.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Your Winchester getaway is meant to be an escape from your daily routine, not a source of money-related stress. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.