Deals on vacations and trips to Winchester

Save when you book Winchester package deals

Choose two or more items and save on your trip:

Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Virgin Hotels Nashville

Virgin Hotels Nashville

4.5 out of 5
Downtown Nashville
Price was $824, price is now $565 per person
$565
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Nashville (BNA)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. You'll appreciate the seasonal outdoor pool, poolside bar, and rooftop terrace.
Hutton Hotel

Hutton Hotel

4.5 out of 5
West End
Save 100% on your flight
Price was $1,166, price is now $709 per person
$709
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Nashville (BNA)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Self parking, dry cleaning, and luggage storage are also offered.
The Hermitage Hotel

The Hermitage Hotel

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $972, price is now $636 per person
$636
per person
Dec 3 - Dec 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
Sleeps 8 4 Sobro Suites w/ Kitchens & Art, Walk to Broadway by Avantstay

Sleeps 8 4 Sobro Suites w/ Kitchens & Art, Walk to Broadway by Avantstay

3 out of 5
Downtown Nashville
Save 100% on your flight
Price was $2,791, price is now $1,919 per person
$1,919
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Nashville (BNA)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace is also provided.
Sleeps 8 Walkable Sobro Suites w/ Local Art & Vibes by Avantstay

Sleeps 8 Walkable Sobro Suites w/ Local Art & Vibes by Avantstay

3 out of 5
Downtown Nashville
Save 100% on your flight
Price was $3,874, price is now $2,664 per person
$2,664
per person
Oct 31 - Nov 6
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Nashville (BNA)
Free WiFi in public areas is available at this cottage.

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
Oct 1 - Oct 2
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.
"The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake

$316 nightly
The price is $361 total per night
$361 total
Sep 28 - Sep 29
Total with taxes and fees
This cabin features barbecue grills.
Reflection Bay-Dock, Hot Tub, Kayaks

Reflection Bay-Dock, Hot Tub, Kayaks

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.
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

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

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

2 out of 5
Get rates
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Beautiful Lake Views at Twin Creeks!

Beautiful Lake Views at Twin Creeks!

Get rates
An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Families will appreciate the arcade/game room and barbecue grills.
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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

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 $565. 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