Deals on vacations and trips to Winchester

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Winchester flight + hotel vacation packages

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Caption by Hyatt Downtown Nashville

Caption by Hyatt Downtown Nashville

3 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,058, price is now $673 per person
$673
per person
May 3 - May 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a business center, and express check-in are also offered.
Margaritaville Hotel Nashville

Margaritaville Hotel Nashville

4.5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,309, price is now $833 per person
$833
per person
May 3 - May 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Make the most of the seasonal outdoor pool and a rooftop terrace, and relax with drinks at one of the 2 bars/lounges.
Hyatt Centric Downtown Nashville

Hyatt Centric Downtown Nashville

4.5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,323, price is now $857 per person
$857
per person
May 3 - May 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.
1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $2,757, price is now $1,824 per person
$1,824
per person
May 3 - May 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
A full-service spa, 2 restaurants, and A 24-hour gym are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. There's a rooftop terrace on site, and a 24-hour front desk and a coffee shop are also provided.
Bode Nashville

Bode Nashville

3.5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,570, price is now $1,049 per person
$1,049
per person
May 3 - May 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
A bar/lounge and a coffee shop are featured at this hotel, along with self parking. WiFi in public areas is free. A terrace, a snack bar/deli, and a grocery/convenience store are also on offer.

Top Winchester hotels deals

Best Western Inn

Best Western Inn

2.5 out of 5
1602 Dinah Shore Boulevard Winchester TN
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $109 total per night
$109 total
Feb 16 - Feb 17
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

2 out of 5
Winchester TN
Get rates
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Reflection Bay-Dock, Hot Tub, Kayaks

Reflection Bay-Dock, Hot Tub, Kayaks

Winchester TN
Get rates
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

2 out of 5
Winchester TN
Get rates
This vacation home featured laundry facilities and barbecue grills.
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK

Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK

Winchester TN
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kayak Kove* DOCK* Lake front Tim's Ford Lake NEW- 2 kayaks

Kayak Kove* DOCK* Lake front Tim's Ford Lake NEW- 2 kayaks

Winchester TN
Get rates
This vacation home featured laundry facilities and barbecue grills.
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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.

Popular places to visit

Aerial drone view of a lake marina with boats storage on Tims Ford lake in Winchester Tennessee

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
Early morning beautiful sky and marina with boats storage, twin creeks on Tims Ford lake in Winchester Tennessee USA

Twin Creeks Marina

Explore the waterfront in Winchester with a trip to Twin Creeks Marina. Amble around the area's lakeside or visit its shops.

Twin Creeks Marina
golf course fairway and green in the fall

Bear Trace Golf Course

Enjoy a round of golf in Winchester at Bear Trace Golf Course. Amble around the area's lakeside or visit its shops.

Bear Trace Golf Course

Frequently asked questions

How much are vacation packages to Winchester?
Travelocity has great package deals to Winchester, as well as flights and hotels, starting at just $673. With the cash you save, you could book some popular tours or possibly tack on a few extra days to your vacation.
How long should my Winchester vacation be?
Your Winchester trip can be as long as you would like it to be, but the majority of people stay around 2 nights. Can't wait to head off the beaten path and uncover some less touristy sights? Lock in an extra night or two and experience a different side of this place.
Where can I get the best vacation package deals for Winchester?
You'll come across a fantastic range of Winchester package deals on Travelocity. With 400 air carriers and 1,000,000 properties across the globe, arranging the perfect getaway will be easy.
Why should I purchase my Winchester vacation package via Travelocity?
Because you'll never roam on your own if you secure your trip with us, and we offer round-the-clock customer support and excellent service to boot. Add to that our Price Match Guarantee and countless experiences and destinations to select from. It's our job to make your vacation as unforgettable as possible.
Can I save on my Winchester car rental if I bundle it with my hotel or flight?
With a Winchester vacation package, you can bundle your car, hotel and flight bookings and save a whole lot. If you'd love to discover the best of this impressive area, why not head to Grand Ole Opry? This top attraction is 80 mi from Winchester. With your own set of wheels, you'll be there belong long.
Which airport is best for Winchester?
Huntsville Intl. Airport (HSV) is the starting point of your Winchester getaway. About 55 mi southwest of Winchester, it welcomes travelers from all over every day. Another excellent option is Chattanooga Metropolitan Airport (CHA), 55 mi away from central Winchester.
What is there to do in Winchester?
Winchester has plenty of sights to explore, including Tim's Ford Marina and Hammers. These well-known attractions top most tourists' travel schedules.
Where should I stay when visiting Winchester?
If you're after somewhere to lay your head, have a look at the Best Western Inn. It's the top pick for many travelers.

Photos of local treasures

Browse Winchester vacation photos for more inspiration

High resolution aerial view panorama of lakefront homes, boat docks and beautiful autumn colorful foliage on Tims Ford Lake in Winchester Tennessee USA.
High resolution aerial view panorama of lakefront homes, boat docks and beautiful autumn colorful foliage on Tims Ford Lake in Winchester Tennessee USA.

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