Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Loews Nashville Hotel at Vanderbilt Plaza
Price was $1,078, price is now $808 per person
$808
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
Book a stay at this family-friendly hotel in Nashville. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bridgestone Arena and Ryman Auditorium are located nearby.
Studio 154 Luxury Hotel
Save 100% on your flight
Price was $4,138, price is now $2,726 per person
$2,726
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
Stay at this aparthotel in Nashville. Enjoy free WiFi, a rooftop terrace, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Broadway and Ryman Auditorium are located nearby.
1 Hotel Nashville
Save 100% on your flight
Price was $1,554, price is now $1,041 per person
$1,041
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
Book a stay at this luxury hotel in Nashville. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Bridgestone Arena and Ryman Auditorium are located nearby.
Fairlane Hotel
Price was $1,142, price is now $836 per person
$836
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
Book a stay at this business-friendly hotel in Nashville. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Ryman Auditorium and Broadway are located nearby.
H&O on Music Row
Save 100% on your flight
Price was $1,174, price is now $869 per person
$869
per person
Oct 1 - Oct 3
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
Book a stay at this family-friendly condo in Nashville. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Bridgestone Arena and Ryman Auditorium are located nearby.
Wonderful location and great neighborhood, well appointed and would definitely stay here again!
Reviewed on Mar 18, 2026
The Hermitage Hotel
Save 100% on your flight
Price was $1,400, price is now $1,039 per person
$1,039
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
Book a stay at this luxury hotel in Nashville. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Ryman Auditorium and Broadway are located nearby.
JW Marriott Nashville
Save 100% on your flight
Price was $1,563, price is now $1,172 per person
$1,172
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
Book a stay at this luxury hotel in Nashville. Enjoy an outdoor pool, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Bridgestone Arena and Ryman Auditorium are located nearby.
Great location and fantastic pool!
Reviewed on Aug 26, 2026
Landing Apartments - Downtown Murfreesboro
Price was $1,090, price is now $826 per person
$826
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
Book a stay at this business-friendly apartment in Murfreesboro. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions The Avenue Murfreesboro and Go USA Fun Park are located nearby.
Winchester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Winchester Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Oct 27 - Mon, Nov 16
DEN
Denver Intl.
BNA
Nashville Intl.
$88 Roundtrip, found 10 hours ago
$88
Roundtrip
found 10 hours ago
Thu, Oct 1 - Mon, Oct 5
PHL
Philadelphia Intl.
BNA
Nashville Intl.
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Mon, Sep 28 - Sat, Oct 10
DFW
Dallas-Fort Worth Intl.
BNA
Nashville Intl.
$163 Roundtrip, just found
$163
Roundtrip
just found
Tue, Sep 29 - Thu, Oct 1
DTW
Detroit Metropolitan Wayne County
BNA
Nashville Intl.
$177 Roundtrip, found 1 hour ago
$177
Roundtrip
found 1 hour ago
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