Deals on vacations and trips to Winchester

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Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Nashville/Vanderbilt

Hampton Inn Nashville/Vanderbilt

2.5 out of 5
West End
Save 100% on your flight
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the free buffet breakfast each morning.
Bobby Hotel

Bobby Hotel

4 out of 5
Downtown Nashville
Save 100% on your flight
per person
Sep 5 - Sep 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the seasonal outdoor pool, poolside bar, and rooftop terrace.
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
Bellevue
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A business center, a grocery/convenience store, and a picnic area are also on offer.
The Printing House Hotel, Tapestry Collection By Hilton

The Printing House Hotel, Tapestry Collection By Hilton

3.5 out of 5
Downtown Nashville
Save 100% on your flight
per person
Aug 16 - Aug 23
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This Art Deco hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a snack bar/deli are also offered.
1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
per person
Sep 5 - Sep 9
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.

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
Get rates
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

2 out of 5
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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
"The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake

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This cabin features barbecue grills.
Kitchen
Pet friendly
NEW 2021 Tims Ford Lake Home - Private covered dock - Hot Tub

NEW 2021 Tims Ford Lake Home - Private covered dock - Hot Tub

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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

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A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
Family friendly lake front home with private dock in a cove

Family friendly lake front home with private dock in a cove

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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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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

Tim's Ford Marina

4.5/5(6 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

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

Tims Ford

Commune with nature and explore the great outdoors at Tims Ford during your travels in Winchester. Amble around the area's lakeside or visit its shops.

Tims Ford

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 $387. 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