Deals on vacations and trips to Winchester
Save when you book Winchester package deals
Winchester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Virgin Hotels Nashville
Downtown Nashville
Save 100% on your flight
per person
Jul 18 - Jul 21
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. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. You'll appreciate the seasonal outdoor pool, poolside bar, and rooftop terrace.
Bobby Hotel
Downtown Nashville
per person
Aug 17 - Aug 23
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. 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
Downtown Nashville
Save 100% on your flight
per person
Aug 17 - Aug 23
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.
Fairlane Hotel
Downtown Nashville
Save 100% on your flight
per person
Aug 17 - Aug 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This smoke-free hotel features 2 restaurants, a bar/lounge, and a gym. 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.
Conrad Nashville
Downtown Nashville
Save 100% on your flight
per person
Aug 17 - Aug 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.
Top Winchester hotels deals
Best Western Inn
1602 Dinah Shore Boulevard, Winchester, TN
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $135 total per night
$135 total
Jun 1 - Jun 2
Total includes 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
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
"The Hawk Nest" cabin on Tims Ford Lake
$403 nightly
The price is $461 total per night
$461 total
May 28 - May 29
Total includes taxes and fees
This cabin features barbecue grills.
Kitchen
Pet friendly
Reflection Bay-Dock, Hot Tub, Kayaks
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
Gorgeous Renovated Home with Open Floor Plan and Large Lot
$328 nightly
The price is $345 total per night
$345 total
Jun 3 - Jun 4
Total includes taxes and fees
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
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
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.
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.
Tims Ford
Commune with nature and explore the great outdoors at Tims Ford during your travels in Winchester. Amble around the area's lakeside or visit its shops.
Photos of local treasures
Browse Winchester vacation photos for more inspiration