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Jamestown flight + hotel packages

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Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was CA $1,482, price is now CA $1,317 per person
CA $1,317
per person
Nov 22 - Nov 27
found 2 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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.
The Brown Hotel

The Brown Hotel

4.5 out of 5
Downtown Louisville
Price was CA $1,613, price is now CA $1,408 per person
CA $1,408
per person
Nov 22 - Nov 27
found 2 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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.
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was CA $1,569, price is now CA $1,385 per person
CA $1,385
per person
Nov 22 - Nov 27
found 2 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Kentucky Kingdom and L&N Federal Credit Union Stadium are located nearby.
Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was CA $1,607, price is now CA $1,429 per person
CA $1,429
per person
Nov 22 - Nov 27
found 2 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Louisville (SDF)
Book a stay at this business-friendly 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.
The Grady

The Grady

4 out of 5
Downtown Louisville
Price was CA $1,740, price is now CA $1,557 per person
CA $1,557
per person
Nov 22 - Nov 27
found 2 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Louisville (SDF)
Stay at this hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Louisville Slugger Museum and KFC Yum Center are located nearby.

Top Jamestown hotels deals

Sunset Ridge·Sleeps 16·Panoramic Lake Cumberland Views·3 Decks·Jamestown Marina

Sunset Ridge·Sleeps 16·Panoramic Lake Cumberland Views·3 Decks·Jamestown Marina

Jamestown KY
Get rates
Book a stay at this family-friendly vacation home in Jamestown. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions The Links Resort Golf Course and The Park at Jamestown Square are located nearby.
Kitchen
Washer
Timber Pointe Resort

Timber Pointe Resort

2 out of 5
2671 Kentucky 92 Jamestown KY
The price is CA $141 per night
CA $141
CA $155 total
Oct 9 - Oct 10
includes taxes & fees
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 are located nearby.
Pool
Parking included
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

Jamestown KY
Get rates
Stay at this cottage in Jamestown. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Jamestown Marina and Lake Cumberland State Resort Park are located nearby.
Kitchen
Washer
The Lodge @ Lake Cumberland Fall/Winter Cabin

The Lodge @ Lake Cumberland Fall/Winter Cabin

Jamestown KY
Get rates
Stay at this cabin in Jamestown. Enjoy private pools, a garden, and laundry facilities. Popular attractions Jamestown Marina and Lake Cumberland State Resort Park are located nearby.
Pool
Kitchen
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

Jamestown KY
The price is CA $353 per night
CA $353
CA $713 total
Oct 4 - Oct 5
includes taxes & fees
Stay at this cottage in Jamestown. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions Jamestown Marina and Lake Cumberland State Resort Park are located nearby.
Hot tub
Kitchen
Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay

Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay

Jamestown KY
The price is CA $216 per night
CA $216
CA $585 total
Oct 12 - Oct 13
includes taxes & fees
Stay at this cottage in Jamestown. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Jamestown Marina and Lake Cumberland State Resort Park are located nearby.
Kitchen
Washer
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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.

Stay near popular Jamestown attractions

Wolf Creek National Fish Hatchery

9.0/10 (40 reviews)
Commune with nature and explore the great outdoors at Wolf Creek National Fish Hatchery during your travels in Jamestown. Stroll along this family-friendly area's lakeside, or simply enjoy its restaurants.
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Jamestown Vacations

Even if you're the most impulsive adventurer, it's still good to know a couple of things about Jamestown before you take off. Locate it on your map, investigate the sights on offer and let the good times roll!

It is 19 miles (31 kilometers) away from Monticello and 30 miles (48 kilometers) from Somerset.

Forget the star attractions — it's the locals that really make a place tick. In this part of Lake Cumberland, you'll find 2,000 of them.

Places to visit in Jamestown

Do you want to ease the stresses of your busy life? Savor the fresh air as you head off on an adventure through Lake Cumberland State Resort Park. Still need more ideas? The natural world is a complex and magnificent thing. Wolf Creek National Fish Hatchery is a great place to go to learn all about it.

Where do you fly into for Jamestown?

Fasten your seatbelt, stow your tray table and prepare to experience Jamestown! Once you arrive at Lake Cumberland Regional Airport (SME), the lively main streets will be only 30 miles (48 kilometers) to the west of here.

Frequently asked questions

How much are vacation packages to Jamestown?
Enjoy a one-of-a-kind experience in Jamestown with a vacation package starting from as low as CA $1,317. Locking in your hotels, tours and flights through Travelocity has never been easier. And even better, our vacation deals will leave you with more cash in your pocket for fun times.
How long should my Jamestown vacation be?
The majority of travelers spend roughly 2 nights in Jamestown, but how long you stay is totally up to you. If you hope to discover all the amazing things this destination has to offer, why not hang around for a bit longer?
Where can I get the best vacation package deals for Jamestown?
For an excellent Jamestown package deal, head straight to Travelocity. Pick from as many as 400 partner airlines and 1,000,000 properties around the globe to create your ideal adventure — it couldn't be easier than that.
Why should I book my Jamestown vacation package via Travelocity?
Whether you're searching for the ultimate unplugged getaway or after the fun and excitement that only a big city can provide, booking everything with Travelocity saves you time, money and hassle. No need to sift through hundreds of different websites looking for the best deal — our Price Match Guarantee ensures you'll never be out of pocket, and our team of customer service experts are available for you round-the-clock.
Can I save money on my Jamestown car rental if I combine it with my hotel or flight?
You certainly can — combine your car, hotel and flight into a Jamestown vacation package and you'll save a tidy sum. With so many places to explore in and around Jamestown, having your own wheels will make it easy to explore. Once you've buckled yourself in, crank up the music and find your way to Dollywood, an unmissable attraction about 193 kilometers from Jamestown.
What is there to do in Jamestown?
Jamestown has plenty of sights to explore, like Lake Cumberland State Resort Park and Wolf Creek National Fish Hatchery. These two fantastic attractions are at the top of most people's travel itineraries.
Where should I stay when visiting Jamestown?
The Lake Cumberland State Resort Park is the number one choice of many travelers. Book now to avoid missing out.

Photos of local treasures

Browse Jamestown vacation photos for more inspiration

An aerial view of a coastal area with a lighthouse, a parking lot, and a rocky shoreline.
A sunset over a calm body of water with a bridge silhouetted against the sky.
A long bridge spanning a wide river with a clear sky.
A sunset over a calm lake with trees silhouetted against the sky.
A waterfall cascading down a rocky cliff into a pool.