Jamestown Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Jamestown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Caesars Southern Indiana Hotel & Casino - A Caesars Rewards Destination
$481
per person
Nov 23 - Nov 27
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Louisville (SDF)
Book a stay at this spa hotel in Elizabeth. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Horseshoe Southern Indiana Casino and Waverly Hills Sanatorium are located nearby.
Cottonwood Airport & Expo Hotel Louisville
Shively
$536
per person
Nov 23 - Nov 27
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Churchill Downs and L&N Federal Credit Union Stadium are located nearby.
Hotel Distil, Autograph Collection
Downtown Louisville
$778
per person
Nov 23 - Nov 27
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Whiskey Row and KFC Yum Center are located nearby.
Great hotel, right in the middle of the city.
Reviewed on Sep 27, 2026
Louisville Marriott Downtown
Downtown Louisville
$694
per person
Nov 23 - Nov 27
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions KFC Yum Center and Whiskey Row are located nearby.
Didn’t like the many homeless people right outside on the sidewalk.
Reviewed on Oct 1, 2026
Moxy Louisville Downtown
Downtown Louisville
$622
per person
Nov 23 - Nov 27
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Louisville (SDF)
Book a stay at this family-friendly hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Whiskey Row and KFC Yum Center are located nearby.
The Brown Hotel
Downtown Louisville
$605
per person
Nov 23 - Nov 27
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Louisville (SDF)
Book a stay at this luxury hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions KFC Yum Center and Whiskey Row are located nearby.
We loved the hotel decor, rooms were big and comfortable and the parking was convenient.
Reviewed on Oct 3, 2026
Jamestown Vacation Packages
Trying to plan a way to package your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Jamestown vacation packages can help. We're here to book everything you'll need to make your Jamestown trip one to remember. Our Travel Center is a one-stop shop where you can put together the best Jamestown vacation package for you. AARP Travel Center has an amazing choice of accommodations and flight, and local things to do to pick from.
Hotel Deals in Jamestown
With 654 hotels and resorts in Jamestown to choose from, you will find one that is perfect for you.
We have great deals on everything from all-inclusive resorts that satisfy all the vacation must-haves to inexpensive accommodations perfect for those on looking to save. You can look through our vast catalog of possibilities and pick the lodging that is best for you. With AARP Travel Center's Jamestown hotel packages, you not only get a great rate on your flight, but also a great place to stay.
Things to do in Jamestown
Jamestown is the ideal town when you have to get away from it all. With only around 1,804 people in the city, this quaint town is great for a quite vacation.
The AARP Travel Center "Things to Do" page has more great activities that you can book.
Package Your Jamestown Vacation and Save
As an AARP Member, you get to benefit from all the great savings. You'll save on select hotels worldwide, flights, and also car rentals. No matter what Jamestown vacation bundle you select, your membership savings helps you get a great deal. The hardest packing you'll have to do is for your suitcase. Book now and get ready for your Jamestown vacation.
Top Hotel Deals
Timber Pointe Resort
2671 Kentucky 92 Jamestown KY
Stay at this hotel in Jamestown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Jamestown Marina and Lake Cumberland State Resort Park ...
Dale Hollow Lake State Resort Park
5970 State Park Rd Burkesville KY
Book a stay at this golf hotel in Burkesville. Enjoy free WiFi, free parking, and a marina. Popular attractions Dale Hollow Lake State Park and Dale Hollow State ...
Baymont by Wyndham Albany
79 Soma Ln Albany KY
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mountain View Park and Clinton ...
Days Inn by Wyndham Columbia Kentucky
710 Bomar Hts Columbia KY
Book a stay at this business-friendly hotel in Columbia. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our ...
Sleep Inn & Suites Columbia
350 Dohoney Trace Columbia KY
Book a stay at this business-friendly hotel in Columbia. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our ...
Kozy Haven Log Cabin Rentals
1561 Hwy 55 S Rd Columbia KY
Book a stay at this family-friendly cabin in Columbia. Enjoy free WiFi, free parking, and a picnic area.
Best Western Lake Cumberland Inn
2030 E Highway 90 Monticello KY
Book a stay at this business-friendly hotel in Monticello. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Riverfront Lodge
305 Keen St Burkesville KY
Stay at this motel in Burkesville. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Dr. Joseph Schickel Veterans Memorial Park and Burkesville ...
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.
Fri, Oct 23 - Sun, Oct 25
TPA
Tampa Intl.
SDF
Louisville Intl.
$242
Roundtrip
found 3 days ago
Sat, Nov 7 - Tue, Nov 17
DAL
Love Field
SDF
Louisville Intl.
$257
Roundtrip
found 3 days ago
Tue, Nov 10 - Tue, Nov 17
DAL
Love Field
SDF
Louisville Intl.
$277
Roundtrip
found 3 days ago
Sat, Oct 31 - Mon, Nov 9
DFW
Dallas-Fort Worth Intl.
SDF
Louisville Intl.
$287
Roundtrip
found 4 days ago
Thu, Nov 12 - Thu, Nov 19
TPA
Tampa Intl.
SDF
Louisville Intl.
$320
Roundtrip
found 6 days ago
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All accommodation types in Jamestown
More Types of Hotels
- Hotels with WiFi in Jamestown
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- Hotels with Tennis Courts in Jamestown
- Hotels with smoking rooms in Jamestown
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- Pet-friendly Hotels in Jamestown