Deals on vacations and trips to Winchester

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Winchester flight + hotel vacation packages

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Club - Hotel Nashville Inn & Suites

Club - Hotel Nashville Inn & Suites

3 out of 5
Donelson
Price was $792, price is now $578 per person
$578
per person
May 9 - May 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features an outdoor pool and a gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $3,259, price is now $2,208 per person
$2,208
per person
Jun 24 - Jun 28
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.
Waymore's Guest House

Waymore's Guest House

3.5 out of 5
East Nashville
Save 100% on your flight
Price was $1,179, price is now $821 per person
$821
per person
May 9 - May 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features a restaurant and 2 bars/lounges. WiFi in public areas is free. A coffee shop, a terrace, and a communal living room are also on offer.
The Hermitage Hotel

The Hermitage Hotel

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,311, price is now $941 per person
$941
per person
May 27 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features a restaurant and 2 bars/lounges. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.
Carter by Avantstay Sleeps 22 3 Units in Downtown Nashville Rooftop Views

Carter by Avantstay Sleeps 22 3 Units in Downtown Nashville Rooftop Views

3 out of 5
East Nashville
Save 100% on your flight
Price was $2,260, price is now $1,631 per person
$1,631
per person
Jun 17 - Jun 20
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.

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
$110 nightly
The price is $125 total per night
$125 total
Apr 5 - Apr 6
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
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

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

Winchester TN
Get rates
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
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.
Kitchen
Washer
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

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

Winchester TN
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Winchester TN
Get rates
This vacation home featured laundry facilities and barbecue grills.
Pool
Kitchen
Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

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

Winchester TN
Get rates
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
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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

4.5/5(7 reviews)

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 $578. 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.
Aerial view of a beautiful morning sunrise sky and water reflection over the mountain and lake, marina and Bass Club on beautiful Tims Ford Lake in Winchester Tennessee

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