Winchester Vacation Packages 2026 from $729

Winchester flight + hotel vacation packages

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

Bluegreen Downtown Nashville

Downtown Nashville

$729

per person

Dec 24 - Dec 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Nashville (BNA)

This hotel features free WiFi in public areas, concierge services, and valet parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Bode Nashville

Downtown Nashville

$955

per person

Dec 29 - Jan 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Nashville (BNA)

A bar/lounge and a coffee shop are featured at this hotel, along with self parking. WiFi in public areas is free. A terrace, a snack bar/deli, and a grocery/convenience store are also on offer.

Fairlane Hotel

Downtown Nashville

$948

per person

Dec 21 - Dec 28

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.

1 Hotel Nashville

Downtown Nashville

$848

per person

Dec 16 - Dec 19

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 Hermitage Hotel

Downtown Nashville

Save 100% on your flight

$1,127

per person

Dec 16 - Dec 20

found 9 hours 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.

Top Winchester hotels deals

Best Western Inn

1602 Dinah Shore Boulevard Winchester TN

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$116 total

Oct 20 - Oct 21

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!

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

Enjoy Your Vacation on Tims Ford Lake

Winchester TN

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

Kitchen

Washer

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Winchester TN

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This vacation home featured laundry facilities and barbecue grills.

Pool

Kitchen

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

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.

Hot Tub

Kitchen

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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 $729. 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.