Winchester Vacation Packages

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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.

Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sonesta Nashville Airport

Sonesta Nashville Airport

4 out of 5
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Nashville (BNA)
9/10 Wonderful! (1,623 reviews)
Great breakfast buffet

Reviewed on Jul. 24, 2025

Bobby Hotel

Bobby Hotel

4 out of 5
Downtown Nashville
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Nashville (BNA)
9.2/10 Wonderful! (1,006 reviews)
Room and service were fantastic. Enjoyed rooftop bar.

Reviewed on Jul. 22, 2025

Sentral Sobro

Sentral Sobro

4 out of 5
Downtown Nashville
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Nashville (BNA)
8.8/10 Excellent! (1,456 reviews)
Kitchen Amenities were provided. Walking distance, easy parking.

Reviewed on Jul. 21, 2025

Sleeps 24 4 Modern Midtown Apartments w/ Gym + Pool Walkable to Shops & Eats

Sleeps 24 4 Modern Midtown Apartments w/ Gym + Pool Walkable to Shops & Eats

3 out of 5
West End
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Nashville (BNA)
No reviews
Dual Bachelor Pads w/ Rooftop Lounge & Games Sleeps 26 5 Min to Broadway

Dual Bachelor Pads w/ Rooftop Lounge & Games Sleeps 26 5 Min to Broadway

3 out of 5
East Nashville
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Nashville (BNA)
No reviews

Ready to book your vacation to Winchester?

 

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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 CA $161 per night from Jul 28 to Jul 29
CA $161
CA $184 total
Jul 28 - Jul 29
includes taxes & fees
8.6/10 Excellent! (616 reviews)
"The room was clean and spacious. The staff were friendly that we saw. My husband enjoyed the jetted bathtub. The breakfast was ok. The eggs were very salty. We were nearing the end of breakfast time and they did not refill things. People that came after us did not get some things. We did not use ..."

Reviewed on Jul. 21, 2025

Best Western Inn
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

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

Winchester
10/10 Exceptional! (44 reviews)
Family Vacation
"Our granddaughters loved the dock! Peaceful beautiful setting."

Reviewed on Jul. 2, 2025

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

Reflection Bay-Dock, Hot Tub, Kayaks

Winchester
10/10 Exceptional! (6 reviews)
"Great communication and great location"

Reviewed on Jun. 15, 2025

Get rates
Reflection Bay-Dock, Hot Tub, 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Winchester

Tim's Ford Marina

Bring the kids to Tim's Ford Marina and enjoy the excitement of this amusement park in Winchester. Discover the countryside while you're in the area.

Tim's Ford Marina

Frequently asked questions

How much does a Winchester vacation package cost?
Offering excellent value package deals from CA $944 on Expedia, you'll be surprised at how little a vacation to Winchester costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Winchester?
December, January and February are the best times to look for cheap Winchester vacation packages. Travelling in quieter months means you can usually find lower prices on flights and accommodations.
How many days is enough for Winchester?
The ideal duration for your Winchester vacation depends on what you'd like to see and do. Generally, a handful of days to a week will give you time to visit all the top attractions and discover some hidden spots along the way.
How to find the best Winchester package deals?
Finding a cheap Winchester package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, add some filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most economical Winchester package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking hotels and flights individually. Better still, you can tailor your Winchester escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Winchester?
If you're planning a spontaneous Winchester adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Winchester?

  1. Choose when to go: Check your diary and get packing. Your favourite time of year and the type of activities available will also help you decide when to vacation in Winchester.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and dining out to activities and flights. Your accommodations will probably be the biggest expense during your trip to Winchester.
  3. Set the duration of your trip: Start by listing all the activities and sights you'd like to get to in Winchester. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Winchester vacation package.

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