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.
Sylvan Park Boarding House

Sylvan Park Boarding House

2 out of 5
Sylvan Park
Save 100% on your flight
Price was $710, price is now $451 per person
$451
per person
Aug 20 - Aug 24
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Nashville (BNA)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A garden is also provided.
1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,451, price is now $953 per person
$953
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop 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.
The Hermitage Hotel

The Hermitage Hotel

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,557, price is now $1,061 per person
$1,061
per person
Aug 9 - Aug 14
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.
Chanticleer Inn Bed & Breakfast

Chanticleer Inn Bed & Breakfast

3 out of 5
Save 100% on your flight
Price was $904, price is now $629 per person
$629
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip flight included
New York (NYC) to Chattanooga (CHA)
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like cooked-to-order breakfast and WiFi in public areas. A garden is also provided.
Conrad Nashville

Conrad Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $958, price is now $668 per person
$668
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Relax with a drink at the bar/lounge and enjoy 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
$99 nightly
The price is $113 total per night
$113 total
Jul 5 - Jul 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.
Lakefront w/Private Dock and Walk to Historic Downtown Winchester!

Lakefront w/Private Dock and Walk to Historic Downtown Winchester!

Winchester TN
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This vacation home includes a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room.
Spacious Family Gem: Golf Cart - 2 Ensuites - Pool

Spacious Family Gem: Golf Cart - 2 Ensuites - Pool

Winchester TN
Get rates
This vacation home features an outdoor pool and a gym. Laundry facilities and barbecue grills are also provided.
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

Winchester TN
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A hot tub is featured at this cabin, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Private dock/gazebo on quiet cove. Tims Ford Lake!

Private dock/gazebo on quiet cove. Tims Ford Lake!

Winchester TN
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This vacation home features a garden, laundry facilities, and barbecue grills.
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12

Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12

Winchester TN
$725 nightly
The price is $828 total per night
$828 total
Aug 2 - Aug 3
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
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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.

Stay near popular Winchester attractions

An aerial view of a marina with multiple docks and covered boat storage areas.

Tim's Ford Marina

9.4/10 (16 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.
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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 $451. 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

A calm lake with autumn foliage, a dock, and houses along the shore.
A cathedral interior with intricate ribbed vaults, a large organ, and stained glass windows.
A historic cathedral with Gothic architecture, surrounded by a park with autumn foliage.
A river reflecting the sunset, surrounded by greenery and a distant cityscape.

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