
Winchester Vacations from ¥265,926
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The Latest Winchester Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Bluegreen Downtown Nashville
Downtown Nashville
Price was ¥312,497, price is now ¥265,926 per person
¥265,926
per person
Sep 13 - Sep 17
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Nashville (BNA)
9/10 Wonderful! (475 reviews)
It was a nice spot. A little dated but ultimately got the job with a nice comfy bed.
Reviewed on Jun 20, 2026


Fairlane Hotel
Downtown Nashville
Price was ¥359,714, price is now ¥292,173 per person
¥292,173
per person
Sep 13 - Sep 17
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Nashville (BNA)
9.4/10 Exceptional! (1,013 reviews)
I enjoyed the location and the room was clean. The staff was very helpful and friendly. The bartender was especially nice and made us custom drinks.
Reviewed on Jun 25, 2026

The Untitled Nashville Hotel, Tapestry Collection by Hilton
Downtown Nashville
Price was ¥383,224, price is now ¥319,944 per person
¥319,944
per person
Sep 13 - Sep 17
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Nashville (BNA)
9/10 Wonderful! (295 reviews)
Check-in was at 4:00. We arrived at 3:45 and were told our room would be ready in 15min. At 4:30 it still wasn’t ready and we were told it would be another 40 minutes. The entire lobby was full of people and luggage because no one could check in to their rooms due to them not being cleaned in time.
Reviewed on Jun 23, 2026

Margaritaville Vacation Club Nashville
Downtown Nashville
Price was ¥368,213, price is now ¥313,640 per person
¥313,640
per person
Sep 13 - Sep 17
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) 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
Find the Best Winchester Vacation Packages
Winchester Hotel Deals

Best Western Inn
1602 Dinah Shore Boulevard Winchester TN
Fully refundableReserve now, pay when you stay
The price is ¥16,047 per night from Jun 28 to Jun 29
¥16,047
¥18,334 total
Jun 28 - Jun 29
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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