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.
The Hotel Chalet at The Choo Choo

The Hotel Chalet at The Choo Choo

4 out of 5
Downtown Chattanooga
Save 100% on your flight
Price was $546, price is now $400 per person
$400
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chattanooga (CHA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. A poolside bar, a 24-hour front desk, and a coffee shop are also provided.
1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,783, price is now $1,309 per person
$1,309
per person
Dec 29 - Jan 2
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.
Loews Nashville Hotel at Vanderbilt Plaza

Loews Nashville Hotel at Vanderbilt Plaza

4 out of 5
West End
Price was $874, price is now $644 per person
$644
per person
Nov 8 - Nov 11
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. Families will appreciate the onsite laundry facilities and in-room childcare. WiFi in public areas is free.
Landing Apartments Huntsville near Lake Forest

Landing Apartments Huntsville near Lake Forest

3 out of 5
Save 100% on your flight
Price was $1,880, price is now $1,407 per person
$1,407
per person
Nov 21 - Nov 27
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Huntsville (HSV)
This apartment features a 24-hour gym and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, barbecue grills, and a virtual front desk are also on offer.
Boulevard Stays Downtown Nashville

Boulevard Stays Downtown Nashville

3.5 out of 5
Downtown Nashville
Price was $948, price is now $710 per person
$710
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This aparthotel features free WiFi in public areas, luggage storage, and concierge services. A virtual front desk are provided for your convenience.

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
$101 nightly
The price is $116 total per night
$116 total
Oct 13 - Oct 14
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
Enjoy Your Vacation on Tims Ford Lake

Enjoy Your Vacation on Tims Ford Lake

Winchester TN
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Winchester TN
Get rates
This vacation home featured laundry facilities and barbecue grills.
Pool
Kitchen
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

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

Winchester TN
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

Winchester TN
Get rates
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 $400. 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.
An aerial view of a lakeside community with houses, docks, and autumn foliage.
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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