Deals on vacations and trips to Winchester

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Price found within the past 48 hours. Click for updated prices.
Nashville Airport Marriott

Nashville Airport Marriott

3.5 out of 5
Donelson
Price was $399, price is now $276 per person
$276
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. A free area shuttle is offered as well.
1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,379, price is now $812 per person
$812
per person
Feb 8 - Feb 12
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.
Doubletree by Hilton Chattanooga Hamilton Place

Doubletree by Hilton Chattanooga Hamilton Place

4 out of 5
Hamilton Place
Price was $595, price is now $395 per person
$395
per person
Dec 29 - Jan 3
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chattanooga (CHA)
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, express check-out, and dry cleaning are also offered.
Caption by Hyatt Downtown Nashville

Caption by Hyatt Downtown Nashville

3 out of 5
Downtown Nashville
Save 100% on your flight
Price was $537, price is now $358 per person
$358
per person
Jan 1 - Jan 4
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.
Hyatt Centric Downtown Nashville

Hyatt Centric Downtown Nashville

4.5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $610, price is now $420 per person
$420
per person
Jan 30 - Feb 2
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.

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
Nov 23 - Nov 24
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

2 out of 5
Get rates
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
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.
Hot Tub
Kitchen
Gorgeous Renovated Home with Open Floor Plan and Large Lot

Gorgeous Renovated Home with Open Floor Plan and Large Lot

$327 nightly
The price is $343 total per night
$343 total
Nov 16 - Nov 17
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
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.
Pool
Kitchen
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
$53 nightly
The price is $61 total per night
$61 total
Nov 24 - Nov 25
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
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See all available properties in Winchester
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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 $276. 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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