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.
Baymont by Wyndham Franklin/Cool Springs

Baymont by Wyndham Franklin/Cool Springs

2.5 out of 5
per person
Oct 16 - Oct 22
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Nashville (BNA)
8.2/10 Very Good! (1,261 reviews)
Comfortable for a last minute stay

Reviewed on Aug. 2, 2025

Bobby Hotel

Bobby Hotel

4 out of 5
Downtown Nashville
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Nashville (BNA)
9.4/10 Exceptional! (1,002 reviews)
Nice lobby, nice room, nice rooftop restaurant and pool. Convenient location right next to Printers Alley & 10 min walk to Broadway. Nice 4 star hotel.

Reviewed on Aug. 6, 2025

Sonesta Nashville Airport

Sonesta Nashville Airport

4 out of 5
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Nashville (BNA)
9/10 Wonderful! (1,677 reviews)
Nice property. Clean and in a good area distance wise. Only major issue is parking. It’s $20 a day to self park… other than that, I would stay again.

Reviewed on Aug. 5, 2025

Sentral Sobro

Sentral Sobro

4 out of 5
Downtown Nashville
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Nashville (BNA)
8.8/10 Excellent! (1,480 reviews)
Walking distance to broadway with great food options along the way Rooms were clean and the bed was comfy Amenities were also clean

Reviewed on Aug. 3, 2025

Wingate by Wyndham Goodlettsville

Wingate by Wyndham Goodlettsville

2.5 out of 5
per person
Oct 16 - Oct 22
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Nashville (BNA)
8.2/10 Very Good! (1,000 reviews)
We loved the property. Was the nicest and cleanest hotel on our 2000 mile road trip. Also had the best breakfast.

Reviewed on Jul. 30, 2025

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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 $163 per night from Aug 11 to Aug 12
CA $163
CA $186 total
Aug 11 - Aug 12
includes taxes & fees
8.6/10 Excellent! (619 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! (8 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
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

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

Winchester
10/10 Exceptional! (46 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
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 $381 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.