
Winchester Holidays
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Top Flight + Hotel Deals in Winchester
Price found within the past 48 hours. Click for updated prices.

Radisson Hotel Nashville Airport
Donelson
Price was €250, price is now €196 per person
€196
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
New York (JFK) to Nashville (BNA)
8.8/10 Excellent! (1,070 reviews)
Friendly staff (check in with “T” was great!), clean room and convenient location.
Reviewed on 11 Dec 2025

1 Hotel Nashville
Downtown Nashville
Save 100% on your flight
Price was €665, price is now €414 per person
€414
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
New York (JFK) to Nashville (BNA)
9.2/10 Wonderful! (924 reviews)
Rooms were very clean amenities were appropriate. However, it would’ve been nice to know ahead of time that there’s a $35 resort fee per night, which I did not see disclosed anywhere.
Reviewed on 11 Dec 2025

Dream Nashville, by Hyatt
Downtown Nashville
Price was €352, price is now €252 per person
€252
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
New York (JFK) to Nashville (BNA)
9.2/10 Wonderful! (1,029 reviews)
From the moment we arrived, the service was exceptional! Being welcomed with drinks at check-in was a lovely touch and set the tone for a fantastic stay. The staff went above and beyond to accommodate our parking needs, which we truly appreciated! The hotel itself is stunning - beautiful, well-kept, and inviting. A top-notch experience with outstanding service. We would absolutely stay here again and highly recommend it.
Reviewed on 18 Dec 2025

Holiday Inn Nashville - Vanderbilt (Dwtn) by IHG
West End
Price was €254, price is now €203 per person
€203
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
New York (JFK) to Nashville (BNA)
9/10 Wonderful! (1,285 reviews)
It was central to many things we wanted to do and we appreciated the shuttle so that we didn’t have to pay for parking downtown. But they did make it seem like it made several stops, and it didn’t. It dropped us off and we ended up having to walk several blocks, which was fine but in heels, I wasn’t prepared! Also, I didn’t notice the fee for parking and I didn’t know they did a $50 per night hold on your card for damages which doesn’t get reimbursed for 3-10 business days. It was just a bit inconvenient but the stay overall was great. No complaints. It was very quiet. We didn’t eat breakfast because it was $20 per person, and I’ve never stayed at a Holiday Inn where you had to pay extra for parking AND breakfast. That was surprising.
Reviewed on 22 Dec 2025

Hyatt Place Nashville Airport
Donelson
Price was €251, price is now €203 per person
€203
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
New York (JFK) to Nashville (BNA)
7.8/10 Good! (1,073 reviews)
Rooms were not cleaned good, mirrors not cleaned. All bedding old and needs replaced. Floors needed cleaning. Breakfast was good and hot. Breakfast area needed replaced, broken picture under cooler that contained drinks. Overall area needs a through cleaning and painting.
Reviewed on 21 Dec 2025
Top hotels in Winchester

Best Western Inn
1602 Dinah Shore Boulevard Winchester TN
Fully refundableReserve now, pay when you stay
The price is €90 per night from 25 Dec to 26 Dec
€90
25 Dec - 26 Dec
includes taxes & fees
8.6/10 Excellent! (663 reviews)
Clean room. Quiet - no fans unkess I turned it on. Convenient parking and ice close to rokm.
Reviewed on 18 Dec 2025

Beautiful Lake Views at Twin Creeks!
Winchester TN
9.8/10 Exceptional! (56 reviews)
We had a Great Week!
The house was good. I am taking off a star because the queen bed in the one bedroom was atrocious. There was a mattress sitting on slats that were too far apart and not nearly supportive enough. We could not use that bed. I did not address it with the owner while we were there because I was on vacation ...
Reviewed on 21 Jul 2025

The Smokehouse Lodge and Cabins
844 W Main Street Monteagle TN
Fully refundableReserve now, pay when you stay
The price is €48 per night from 4 Jan to 5 Jan
€48
4 Jan - 5 Jan 2026
includes taxes & fees
8.4/10 Very Good! (1,141 reviews)
The room was spotless. It was the perfect atmosphere before a day on the trails at Coalmont. ONLY suggestion Id have is put a fluffy comforter on the bed. Thank you! Ps. We loved it.
Reviewed on 9 Dec 2025
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
Hammers
Enjoy an outing to Hammers during your stay in Winchester. Stroll along the lakeside or discover the area's mountain views.
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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.
