Winchester Vacation Packages
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Your Winchester Vacation
The rich history and spectacular views are just the start of the things Winchester has on offer. Experience the very best of this interesting city your way with a tailor-made Winchester vacation package. Any trip to Winchester should include some sightseeing. Hammers is a great place to kick things off. Whoever you're going away with and whatever you want to spend, your dream Winchester vacation is just a few clicks away with Expedia.
Top Winchester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Graduate by Hilton Nashville
West End
Price was CA $1,481, price is now CA $1,109 per person
CA $1,109
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Nashville (BNA)
9.2/10 Wonderful! (1,196 reviews)
I love how cute aesthetic and girly the hotel was
Reviewed on Jun 26, 2026
1 Hotel Nashville
Downtown Nashville
Price was CA $3,209, price is now CA $2,319 per person
CA $2,319
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Nashville (BNA)
9.4/10 Exceptional! (1,005 reviews)
Outstanding room and bathroom, lobby and rooftop. Very quiet floor. Great if you have a dog as well. Breakfast is not free, area is nice and wide open, well-decorated. Super nice brunch, but NYC prices. Employees were not nice when I stopped the car in front of the lobby to drop luggage, and my wife and 4-year boy. I needed 45 seconds only and the employee was unpleasant. And we've been in the 1 Hotel in the Central Park and Brooklyn. I had to insist in dropping my luggage before parking y car myself across the street.
Reviewed on Jun 23, 2026
Margaritaville Vacation Club Nashville
Downtown Nashville
Price was CA $1,644, price is now CA $1,234 per person
CA $1,234
per person
Sep 14 - Sep 17
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Nashville (BNA)
8.8/10 Excellent! (90 reviews)
This room was fantastic. It was clean it was comfortable and had a beautiful view. It even had a signature Jimmy Buffet Margarita machine. We loved it! It was out second stay at this hotel. I would highly recommend it!
Reviewed on Nov 26, 2025
The Harpeth Franklin Downtown, Curio Collection by Hilton
Historic Downtown Franklin
Price was CA $1,702, price is now CA $1,289 per person
CA $1,289
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Nashville (BNA)
9.6/10 Exceptional! (546 reviews)
This was the perfect stay for our mother/daughter trip. The staff went above and beyond to make our stay memorable.
Reviewed on Jun 24, 2026
Winchester Hotel Deals
Best Western Inn
1602 Dinah Shore Boulevard Winchester TN
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Jul 19 to Jul 20
CA $141
CA $161 total
Jul 19 - Jul 20
includes taxes & fees
8.8/10 Excellent! (718 reviews)
"Fine for what it was. Room was very humid and musty. Check in was easy and staff was nice. Breakfast was basic but ok."
Reviewed on Jun 23, 2026
Lakefront w/Private Dock and Walk to Historic Downtown Winchester!
Winchester TN
10/10 Exceptional! (3 reviews)
"Absolutely amazing time and experience at Amy’s Lake house!! The pictures are as shown. Beautiful house that was perfect for my families lake vacation. Plenty of room for everyone. Large kitchen for cooking and sharing meals together and a dock for our two boats. Each bedroom had a very nice mattress ..."
Reviewed on Jun 18, 2026
Spacious Family Gem: Golf Cart - 2 Ensuites - Pool
Winchester TN
10/10 Exceptional! (33 reviews)
"Great place and great host. Neighborhood pools were fabulous for the kids, especially the heated one because it was still early in the summer and the water at the lake was still cold. House has tons of room and the back porch was great to relax at the end of the day. Will definitely return in the ..."
Reviewed on May 28, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
