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
Price was CA $1,021, price is now CA $629 per person
CA $629
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Nashville (BNA)
9/10 Wonderful! (1,684 reviews)
Great stay and very comfortable beds

Reviewed on Aug. 18, 2025

Sentral Sobro

Sentral Sobro

4 out of 5
Downtown Nashville
Price was CA $1,171, price is now CA $705 per person
CA $705
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Nashville (BNA)
8.8/10 Excellent! (1,481 reviews)
We love all that it has to offer. GREAT amenities, wonderful space, furnished well, once checked in, we fell in love. We frequent this area and will stay again Cons:The desk seemed super overwhelmed and it was hard to get ahold of them. The shower also wasn’t super clean, and the water pressure left us feeling like we couldn’t get clean.

Reviewed on Aug. 20, 2025

The Outrider by AvantStay Chic Stay Close to Broadway

The Outrider by AvantStay Chic Stay Close to Broadway

3.5 out of 5
East Nashville
Price was CA $1,899, price is now CA $1,277 per person
CA $1,277
per person
Nov 5 - Nov 12
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Nashville (BNA)
9.4/10 Exceptional! (9 reviews)
The property is set up perfectly for a larger group - which is why we selected it. The shared spaces allowed folks to be together without being on top of one another. There is a cute bar and coffee shop a stone’s throw away and we loved both of them. There were two dead roaches we found which did concern us but the property did respond accordingly. However we had no major issues with cleanliness otherwise. There is some light wear and tear around the unit.

Reviewed on Jun. 30, 2025

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Price was CA $3,785, price is now CA $2,568 per person
CA $2,568
per person
Nov 1 - Nov 8
found 19 hours ago
Roundtrip flight included
Edmonton (YEG) to Nashville (BNA)
9.2/10 Wonderful! (818 reviews)
Loved the rooftop bar! Incredible cocktails & service given by Serena the bartender.

Reviewed on Aug. 18, 2025

Virgin Hotels Nashville

Virgin Hotels Nashville

4.5 out of 5
Downtown Nashville
Price was CA $1,577, price is now CA $1,071 per person
CA $1,071
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Nashville (BNA)
9.4/10 Exceptional! (2,200 reviews)
Great style, great design in the guest rooms and throughout the hotel, great pool even if small, fun vibe overall!

Reviewed on Aug. 19, 2025

Ready to book your vacation to Winchester?

 

Choose your dates

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 $152 per night from Aug 25 to Aug 26
CA $152
CA $174 total
Aug 25 - Aug 26
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 Jul. 25, 2025

Best Western Inn
Reflection Bay-Dock, Hot Tub, Kayaks

Reflection Bay-Dock, Hot Tub, Kayaks

Winchester
10/10 Exceptional! (9 reviews)
Perfect getaway
"We loved everything about our stay. The place was clean and well stocked. The dock was perfect for fishing (we brought our own gear). The Kayaks and floating Lilly Pad provided hours of entertainment. The hot tub was clean. A large dining table for meals and games. Living room had lots of comfortable ..."

Reviewed on Aug. 1, 2025

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Reflection Bay-Dock, Hot Tub, Kayaks
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

Get rates
Spacious Lakefront Retreat w/ Hot Tub + Dock!
See all 652 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 $629 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.