Winchester Vacation Packages 2026 from $640

Winchester flight + hotel vacation packages

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

Hutton Hotel

West End

Save 100% on your flight

$640

per person

Jul 24 - Jul 27

found 1 day ago

Roundtrip flight included

New York (NYC) 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 Harpeth Franklin Downtown, Curio Collection by Hilton

Historic Downtown Franklin

Save 100% on your flight

$1,663

per person

Jun 23 - Jun 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Nashville (BNA)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Valet parking, a business center, and a coffee shop are also offered.

1 Hotel Nashville

Downtown Nashville

Save 100% on your flight

$1,332

per person

Jun 18 - Jun 21

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.

Sleeps 24 Group-friendly Sobro Stay Near Music & Downtown by Avantstay

Downtown Nashville

Save 100% on your flight

$6,229

per person

Aug 10 - Aug 15

found 12 hours ago

Roundtrip flight included

Philadelphia (PHL) to Nashville (BNA)

Free WiFi in public areas and a terrace are available at this cottage.

Sleeps 16 2 Homes Next Door + Walk to Dining & Music Lischey Loft & The Bloom House by Avantstay

East Nashville

$1,368

per person

Jun 30 - Jul 5

found 1 day ago

Roundtrip flight included

New York (LGA) to Nashville (BNA)

Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.

Top Winchester hotels deals

Best Western Inn

1602 Dinah Shore Boulevard Winchester TN

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$120 total

May 19 - May 20

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

Reflection Bay-Dock, Hot Tub, Kayaks

Winchester TN

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.

Hot Tub

Kitchen

Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK

Winchester TN

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This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Lg lakefront family home with a covered dock and jet-ski port! Nicely remodeled!

Winchester TN

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This vacation home features a gym and a sauna. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden and barbecue grills are also provided.

Kitchen

Washer

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.

Kitchen

Washer

New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

Winchester TN

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This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

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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

Aerial drone view of a lake marina with boats storage on Tims Ford lake in Winchester Tennessee

Tim's Ford Marina

4.5/5(7 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.

Early morning beautiful sky and marina with boats storage, twin creeks on Tims Ford lake in Winchester Tennessee USA

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.

golf course fairway and green in the fall

Bear Trace Golf Course

Enjoy a round of golf in Winchester at Bear Trace Golf Course. Amble around the area's lakeside or visit its shops.

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 $640. 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.