Deals on vacations and trips to Winchester

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Home2 Suites by Hilton Nashville Vanderbilt, TN

Home2 Suites by Hilton Nashville Vanderbilt, TN

3 out of 5
Music Row
Price was $646, price is now $469 per person
$469
per person
Feb 13 - Feb 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Nashville (BNA)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
Music City Lofts

Music City Lofts

4 out of 5
Downtown Nashville
Save 100% on your flight
Price was $2,970, price is now $1,910 per person
$1,910
per person
Mar 16 - Mar 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Nashville (BNA)
This apartment includes luggage storage and laundry facilities.
The Hermitage Hotel

The Hermitage Hotel

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,136, price is now $797 per person
$797
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 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 $3,631, price is now $2,601 per person
$2,601
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Nashville (BNA)
Free WiFi in public areas is available at this cottage.
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 $3,631, price is now $2,601 per person
$2,601
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Nashville (BNA)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace is 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
$93 nightly
The price is $106 total per night
$106 total
Dec 28 - Dec 29
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
Beautiful Lake Views at Twin Creeks!

Beautiful Lake Views at Twin Creeks!

Winchester TN
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.
Pool
Kitchen
Modern Charm with Rare Flat Lot, Dock, Game Area

Modern Charm with Rare Flat Lot, Dock, Game Area

Winchester TN
Get rates
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

2 out of 5
Winchester TN
Get rates
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Pool
Hot Tub
The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

3 out of 5
844 W Main Street Monteagle TN
Free Cancellation
Reserve now, pay when you stay
$44 nightly
The price is $51 total per night
$51 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
A restaurant and an outdoor pool are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A 24-hour business center, a garden, and a lobby fireplace are also on offer.
Pool
Pet friendly
Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

2 out of 5
201 Expressway Dr Manchester TN
Free Cancellation
Reserve now, pay when you stay
$63 nightly
The price is $74 total per night
$74 total
Dec 27 - Dec 28
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and onsite conference space. An outdoor pool is provided and the front desk is staffed around-the-clock.
Pool
Breakfast included
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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 $469. 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.

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