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.
Club - Hotel Nashville Inn & Suites

Club - Hotel Nashville Inn & Suites

3 out of 5
Donelson
Price was $704, price is now $531 per person
$531
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features an outdoor pool and a gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $2,137, price is now $1,487 per person
$1,487
per person
Oct 1 - Oct 4
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.
The Gilmore, an AvantStay Hotel

The Gilmore, an AvantStay Hotel

4 out of 5
12 South
Save 100% on your flight
Price was $1,156, price is now $828 per person
$828
per person
Sep 21 - Sep 26
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
A rooftop terrace, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A garden, express check-in, and express check-out are also on offer.
Fairlane Hotel

Fairlane Hotel

4 out of 5
Downtown Nashville
Price was $1,021, price is now $767 per person
$767
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A coffee shop, a terrace, and dry cleaning are also on offer.
The Untitled Nashville Hotel, Tapestry Collection by Hilton

The Untitled Nashville Hotel, Tapestry Collection by Hilton

3.5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,364, price is now $1,027 per person
$1,027
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
A restaurant and a 24-hour gym are featured at this hotel. WiFi in public areas is free. Valet parking is offered and the front desk is staffed around-the-clock.

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 14 - Jul 15
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
Lakefront w/Private Dock and Walk to Historic Downtown Winchester!

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

Winchester TN
Get rates
This vacation home includes a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room.
Kitchen
Washer
Tim's Ford Lakefront Home

Tim's Ford Lakefront Home

Winchester TN
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This vacation home features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Private dock/gazebo on quiet cove. Tims Ford Lake!

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

Winchester TN
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Lakefront Farmhouse | 14 Guests | Tims Ford Lake

Lakefront Farmhouse | 14 Guests | Tims Ford Lake

Winchester TN
Get rates
Stay at this vacation home in Winchester. Enjoy balconies, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Dry Creek Beach and Twin Creeks Marina are located nearby.
Kitchen
Washer
Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!

Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!

Winchester TN
$314 nightly
The price is $330 total per night
$330 total
Jul 20 - Jul 21
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
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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.

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 $531. 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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