Title: Jamestown Vacation Packages & Trips 2026 from CA $1,097 | Expedia.ca

[Hotels in Jamestown](https://expedia.ca/Jamestown-Hotels.d183256.Travel-Guide-Hotels)[Vacation Rentals in Jamestown](https://expedia.ca/Jamestown-Vacation-Rentals.d183256.Travel-Guide-VacationRentals)[Jamestown Car Rentals](https://expedia.ca/Car-Rentals-In-Jamestown.d183256.Car-Rental-Guide)

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# Jamestown Vacation Packages

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#### Your Jamestown Vacation

When you choose a Jamestown vacation package, you can kick back and enjoy your adventure to the fullest. Delve into the best parts of this fascinating city knowing that all the travel planning has been taken care of before you go. Hoping to do a little sightseeing? Spend some time enjoying well-known attractions like [Lake Cumberland State Resort Park](https://www.expedia.ca/Lake-Cumberland-State-Resort-Park-Jamestown.d553248621532656065.Vacation-Attraction) during your trip to Jamestown. A few clicks is all it takes to create the ideal Jamestown vacation on Expedia.

## Top Jamestown Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Hilton Garden Inn Louisville Mall of St. Matthews](https://images.trvl-media.com/lodging/20000000/19430000/19423600/19423555/78130bf4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Garden Inn Louisville Mall of St. Matthews

St. Matthews

CA $1,097

per person

Mar 18 - Mar 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Louisville (SDF)

9.4/10 Exceptional! (835 reviews)

Room was spotless, amenities was up to date, and the location was perfect....... Will be booking here again!

Reviewed on Feb 1, 2026

![Louisville Marriott Downtown](https://images.trvl-media.com/lodging/2000000/1120000/1111400/1111358/6dbe73d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Louisville Marriott Downtown

Downtown Louisville

CA $1,479

per person

Mar 18 - Mar 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Louisville (SDF)

9/10 Wonderful! (1,003 reviews)

Room was spotless. Staff was top notch. Amenities as expected but I did expect a microwave in the room. There wasn't one. 9/10 experience. Will definitely book again!

Reviewed on Jan 16, 2026

![Galt House Hotel Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/200000/191500/191434/b5c46c3f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Galt House Hotel Trademark Collection by Wyndham

Downtown Louisville

CA $1,308

per person

Mar 18 - Mar 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Louisville (SDF)

9/10 Wonderful! (3,770 reviews)

The rooms are amazing!!!

Reviewed on Feb 8, 2026

![The Grady](https://images.trvl-media.com/lodging/62000000/61220000/61216000/61215907/f322db40_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Grady

Downtown Louisville

CA $1,661

per person

Mar 18 - Mar 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Louisville (SDF)

9.4/10 Exceptional! (1,001 reviews)

Property was very well taken care of and unique. Staff was friendly and helpful. Room was very nice and the price was great!

Reviewed on Feb 3, 2026

![Derby City Gaming & Hotel -  A Churchill Downs Property ](https://images.trvl-media.com/lodging/94000000/93190000/93187900/93187879/ee0d92e3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Derby City Gaming & Hotel - A Churchill Downs Property 

CA $4,695

per person

Apr 30 - May 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Louisville (SDF)

9.4/10 Exceptional! (1,606 reviews)

The room was clean and ready for us when we arrived. Would like to see makeup remover towel and wipes like they have at the Oak Grove facility. Staff at check out was polite and quick. The staff for the bars could use a little help. Seen a lot standing around and did not seem to be in any hurry to serve unless you were a regular. Need to have more staff behind the bars.

Reviewed on Feb 9, 2026

## Ready to book your vacation to Jamestown?

Choose your dates

## Jamestown Hotel Deals

![LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.](https://images.trvl-media.com/lodging/62000000/61480000/61478500/61478411/b7e291b0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

 Jamestown KY

CA $239

CA $712 total

Feb 10 - Feb 11

includes taxes & fees

9.8/10 Exceptional! (160 reviews)

The location and the host is awesome.

Reviewed on Jan 21, 2026

[](https://expedia.ca/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%2F02%2F2026&selected=61478411&PinnedHotelID=61478411&HadPinnedHotel=true&regionId=183256)

![Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

](https://images.trvl-media.com/lodging/101000000/100890000/100883400/100883393/aecf157c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina! 

 Jamestown KY

9.8/10 Exceptional! (26 reviews)

We had a wonderful stay here! There are two single bed rooms, and one room with two full (queen possibly?) bunk beds. So 6 big beds all together and the couch pulls out as well. Check in and check out instructions were clear. There were corn hole boards and bags available. The hot tub was great, ...

Reviewed on Oct 30, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=100883393&PinnedHotelID=100883393&HadPinnedHotel=true&regionId=183256)

[](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=100883393&PinnedHotelID=100883393&HadPinnedHotel=true&regionId=183256)

![Charming 5-bedroom/3-bath home with easy access to Lake Cumberland](https://images.trvl-media.com/lodging/112000000/111190000/111182200/111182137/aff3777e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Charming 5-bedroom/3-bath home with easy access to Lake Cumberland

 Jamestown KY

9.6/10 Exceptional! (5 reviews)

We enjoyed a great time at Lake Cumberland! Jennifer was so helpful when we had questions, and communication was easy. The home was a good size for us, and though we didn't need to use the bunk rooms, they are a great space for larger groups/kids. The driveway was also large enough to accommodate ...

Reviewed on Sep 13, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=111182137&PinnedHotelID=111182137&HadPinnedHotel=true&regionId=183256)

[](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=111182137&PinnedHotelID=111182137&HadPinnedHotel=true&regionId=183256)

[See all 570 properties in Jamestown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F02%2F2026&endDate=11%2F02%2F2026&regionId=183256)

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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All Inclusive Vacations

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Beach Vacations

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Family Vacations

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Golf Vacations

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Luxury Vacations

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Romantic Vacations

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Ski Vacations

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