Winchester Vacations

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Winchester Flight + Hotel packages

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Dream Nashville, by Hyatt

Dream Nashville, by Hyatt

Downtown Nashville
$677
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Nashville (BNA)
Book a stay at this business-friendly hotel in Nashville. Enjoy free WiFi, 5 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ryman Auditorium and Broadway are located nearby.
Noelle

Noelle

Downtown Nashville
$748
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Nashville (BNA)
Book a stay at this business-friendly hotel in Nashville. Enjoy 3 restaurants, 2 bars/lounges, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ryman Auditorium and Broadway are located nearby.
The hotel was great. The staff. Rooms are big and comfortable. Excellent bathroom and bathrobe. Rooftop bar is amazing

Reviewed on Sep 14, 2026

The Hermitage Hotel

The Hermitage Hotel

Downtown Nashville
Save 100% on your flight
$1,063
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (ORL) 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.
Landing Apartments Midtown Nashville

Landing Apartments Midtown Nashville

West End
$929
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Nashville (BNA)
Book a stay at this business-friendly apartment in Nashville. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Popular attractions Bridgestone Arena and Ryman Auditorium are located nearby.
I rented the apartment for a week long conference at Vanderbilt univ. and I shared it with a colleague. The apartment is on one of those soulless high rises that are sprouting in Nashville. The remote verification process was very tedious. I had to submit a scanned copy of my driver license and other sensitive information. I called Landing two days before my trip to ask whether the check-in information would be sent also to my colleague; they said yes, but she did not receive any instruction. The steps for retrieving the key and locating our apartment were clear and we had no problems there, but only one key was provided. In the apartment we found a Keurig machine, but no coffee, tea, or sugar. The next day we stepped into the office on the first floor of the building to ask for coffee and another key but we were told that they have no connection with Landing and could not help us. I received a “welcome “ text, with a number for emergencies; when I texted asking for another key and basic supplies, I did not get any reply. My colleague and I had to cope with our single key for the whole week. The checkout process was troublesome and we couldn’t figure out how to return the key. We left it in the apartment, with fingers crossed. Luckily, when I reported the problem via text, I got a reply that confirmed that the key had been found. The place was nice and we had a good stay altogether, but it could’ve been made smoother with little effort from Landing

Reviewed on May 25, 2026

3203 Long BLVD

3203 Long BLVD

West End
Save 100% on your flight
$1,173
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Nashville (BNA)
Book a stay at this business-friendly condo in Nashville. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Bridgestone Arena and Ryman Auditorium are located nearby.
Yes all rooms were clean and staff was helpful

Reviewed on Feb 24, 2026

Landing Furnished Apartments near Barfield

Landing Furnished Apartments near Barfield

$832
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Nashville (BNA)
Book a stay at this business-friendly apartment in Murfreesboro. Enjoy free parking, an outdoor pool, and a fitness center. Popular attractions Indian Hills Golf Course and Barfield Crescent Park are located nearby.
When we first arrived we were greeted by a huge leak in the laundry room and bathroom that I’m not sure how whoever prepared the unit for our arrival did not see. We had fans and de-humidifier machine for some days that were loud and made it hard for me to drown out when I was in work meetings as I work remotely. After the leak was fixed someone was supposed to come back to patch up the holes which seemed like bugs were coming from because we found more bugs than we did before the ceiling was opened. The ceiling was not fixed until the day before we left. The instructions to open the gate were inaccurate. I reached out several times and received one phone call about it and was supposed to get a follow up call that never happened. I’ve had multiple stays with the Landing and we’ve loved them, but this stay was not worth the over $3000 I paid to stay at this property.

Reviewed on Jul 19, 2026

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Winchester Vacation Packages

Looking to save money and time on your upcoming trip to Winchester? Then look no further, as the AARP Travel Center Powered by Expedia® is here to help. We're here to book everything you'll need to make your Winchester trip one to remember. Our Travel Center is a one-stop shop where you can put together the best Winchester vacation package for you and your family. AARP Travel Center has an incredible list of accommodations and flight, as well as Winchester activities to choose from.

Winchester Hotels

Our listings include lodgings that are close to all the Winchester points of interest, and some that are just outside the city center for a more restful retreat.

We have competitive rates on everything from family-friendly resorts that satisfy all the vacation must-haves to inexpensive hotels perfect for those on looking to save. You can browse all the possibilities and pick the accommodation that is ideal for you and your family. With AARP Travel Center's Winchester hotel packages, you not only get a great rate on your flight, but also a great place to stay.

Things to do in Winchester

Winchester is the ideal spot when you have to get away from it all. With only around 8,539 people in the city, this hidden-gem is good for a quite vacation.

If you need more suggestions, then make sure to click on AARP's "Things to Do" page.

Save with a Winchester Vacation Package

As an AARP Member, you can cash in on all the great deals. You'll save on select hotels worldwide, flights, and even car rentals. No matter what Winchester vacation package you choose, you can rest easy knowing that you already saved on your trip. The hardest packing you'll have to do is for your suitcase. Bundle now and get ready for your Winchester vacation.

Top Hotel Deals

Best Western Inn

Best Western Inn

1602 Dinah Shore Boulevard Winchester TN
2.24 km from city center
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the ...
The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

844 W Main Street Monteagle TN
24.25 km from city center
Stay at this hotel in Monteagle. Enjoy free parking, private pools, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

201 Expressway Dr Manchester TN
30.97 km from city center
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

120 Hospitality Blvd Manchester TN
30.84 km from city center
Stay at this hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Quality Inn Monteagle

Quality Inn Monteagle

509 W Main St Monteagle TN
25.08 km from city center
Stay at this hotel in Monteagle. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Spark by Hilton Kimball

Spark by Hilton Kimball

205 Kimball Crossing Dr Jasper TN
41.98 km from city center
Stay at this hotel in Jasper. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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