Winchester Vacation Packages

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Flight and hotel packages to Winchester

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

Bobby Hotel

4 out of 5
Downtown Nashville
Save 100% on your flight
per person
Jun 27 - Jun 30
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the seasonal outdoor pool, poolside bar, and rooftop terrace.
1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
per person
Jul 25 - Jul 28
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.
Thompson Nashville, by Hyatt

Thompson Nashville, by Hyatt

4.5 out of 5
Downtown Nashville
Save 100% on your flight
per person
Jun 27 - Jun 30
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features a restaurant, a 24-hour 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 library, and express check-out are also on offer.
Hyatt Centric Downtown Nashville

Hyatt Centric Downtown Nashville

4 out of 5
Downtown Nashville
Save 100% on your flight
per person
Jul 23 - Jul 29
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.
Dream Nashville, by Hyatt

Dream Nashville, by Hyatt

4 out of 5
Downtown Nashville
Save 100% on your flight
per person
Jun 27 - Jun 30
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This hotel features 5 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A restaurant, a 24-hour front desk, and concierge services are also provided.

Top Winchester hotel 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
The price is $110 per night
$110
per night
May 19 - May 20
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.
Family friendly lake front home with private dock in a cove

Family friendly lake front home with private dock in a cove

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This vacation home includes a garden and barbecue grills.
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK

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

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This vacation home features a water park, a garden, and barbecue grills.
Outdoor Space
Kitchen
Luxurious Waterfront Oasis on Tims Ford Lake!

Luxurious Waterfront Oasis on Tims Ford Lake!

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This vacation home features free WiFi in public areas, a garden, and barbecue grills.
Million Dollar Views: Lakefront, Dock, Kayaks+More

Million Dollar Views: Lakefront, Dock, Kayaks+More

The price is $249 per night
$249
per night
May 14 - May 15
A spa tub is featured at this vacation home, along with a garden and barbecue grills.
Hot Tub
Fireplace
Exquisite Tranquil Lake View Prime Location, Community Dock, private boat slip

Exquisite Tranquil Lake View Prime Location, Community Dock, private boat slip

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This vacation home features barbecue grills.
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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 in Winchester

Image for Tim's Ford Marina

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
Image for Hammers

Hammers

4/5(16 reviews)

Enjoy an outing to Hammers during your stay in Winchester. Stroll along the lakeside or discover the area's mountain views.

Hammers
Image for Expressions

Expressions

4/5(7 reviews)

Enjoy an outing to Expressions during your stay in Winchester. Amble around the area's lakeside or experience its musical theater.

Expressions

Photos of local treasures

Frequently asked questions

How much are vacation packages to Winchester?
Exciting adventures await in Winchester, with Travelocity vacation packages from as little as $774. Providing both flights and hotels, these terrific deals make it simple to see every corner of the globe.
How long should my Winchester vacation be?
Typically, 2 nights is what many visitors book for their Winchester vacation. That’s a good guide, but there’s so much more to discover if you give yourself a little longer.
Where can I get the best vacation package deals for Winchester?
Travelocity is the place to go to score a sensational Winchester package deal. Select from as many as 400 partner airlines and 1,000,000 properties across the globe and create a travel itinerary that’s suited to you. With almost endless choice, it’s easy to plan your next great escape.
Why should I purchase my Winchester vacation bundle with Travelocity?
From enticing destinations to thrilling experiences, we have everything you need to appease your wanderlust. Our 24/7 customer care will also make sure you’re being taken care of before, during and after your getaway. And don’t panic if you notice a cheaper price on your reservation, we’ll match it. That’s our Price Match Guarantee.
Can I save money on my Winchester car rental if I book it with my hotel or flight?
With a Winchester vacation package, you can combine your flight, hotel and car bookings and save a whole lot. If you can’t wait to discover the best of this fabulous location, why not make tracks to Grand Ole Opry? This top sight is 80 mi from Winchester. With your own wheels, you’ll be there in the blink of an eye.
What is the best time of year to go to Winchester?
It comes down to whether you’d like to save money or visit Winchester at its most exciting. The quietest time to explore this part of the world is October, November and December. If you’d like to experience this destination at its busiest, consider April, June and August. Want to save your hard-earned cash? The most affordable month is . typically has the most expensive prices.
Which airport is best for Winchester?
Huntsville Intl. Airport (HSV) is one place you can start your Winchester adventure. Located 55 mi southwest of Winchester, it welcomes visitors from all over every day. Your other option is Chattanooga Metropolitan Airport (CHA), 55 mi away from central Winchester.
What is there to do in Winchester?
There’s a certain magic as you roam the streets of Winchester. Tims Ford Marina and Hammers are just a couple of famous attractions that make this city so popular, so put them on your to-do list.
Where should I stay when visiting Winchester?
The Best Western Inn is the number one choice of many visitors. Book now before it’s too late.