Jamestown Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Jamestown holiday rentals

Dining

New Near Jamestown Dock - A

New Near Jamestown Dock - A
Jamestown
9.8 out of 10, Exceptional, (23 reviews)
"Great stay"
United States
Rob W.
The price is HK$705
HK$1,598 total
includes taxes & fees
2 Jun - 3 Jun
New Near Jamestown Dock - A
Sauna

Guest Favorite! Super Clean! Close to Everything!

Guest Favorite! Super Clean! Close to Everything!
Jamestown
10.0 out of 10, Exceptional, (10 reviews)
"Very clean and all amenities set up perfectly for our stay. Made a perfect middle ground for visiting mammoth caves and cumberland falls."
United States
Brice L.
The price is HK$933
HK$1,987 total
includes taxes & fees
14 Jun - 15 Jun
Guest Favorite! Super Clean! Close to Everything!
Smart TV

The Bourbon House

The Bourbon House
Jamestown
10.0 out of 10, Exceptional, (10 reviews)
"Owner was so friendly and helpful, and the property was clean and fresh on arrival! "
United States
Anonymous traveller
The price is HK$1,175
HK$2,212 total
includes taxes & fees
11 Jun - 12 Jun
The Bourbon House
2 bedrooms, free WiFi

Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky

Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Jamestown
8.8 out of 10, Excellent, (10 reviews)
"Nice location- property manager was bery nice and responsive"
United States
Stephen
The price is HK$784
HK$1,469 total
includes taxes & fees
1 Jun - 2 Jun
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Exterior

Cabin w/ Firepit~Pickleball~Arcade Games~River Boat Ramp~20 Min Lake Cumberland

Cabin w/ Firepit~Pickleball~Arcade Games~River Boat Ramp~20 Min Lake Cumberland
Jamestown
10.0 out of 10, Exceptional, (3 reviews)
"Nice place with boat ramp."
United States
Josh S.
The price is HK$739
HK$3,156 total
includes taxes & fees
1 Jun - 2 Jun
Cabin w/ Firepit~Pickleball~Arcade Games~River Boat Ramp~20 Min Lake Cumberland
Smart TV, fireplace

NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build

NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
Jamestown
9.2 out of 10, Wonderful, (15 reviews)
"Such a lovely property. Very cozy and inviting. We will definitely stay again."
United States
Jennifer S.
The price is HK$892
HK$3,195 total
includes taxes & fees
1 Jun - 2 Jun
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
Outdoor spa tub

HOT TUB~Dog Friendly Cabin~Fishing~River boat ramp~20 Min to Lake Cumberland

HOT TUB~Dog Friendly Cabin~Fishing~River boat ramp~20 Min to Lake Cumberland
Jamestown
10.0 out of 10, Exceptional, (4 reviews)
"Wanted a place close to the river and a boat ramp Great place highly recommend"
United States
doug c.
The price is HK$916
HK$3,231 total
includes taxes & fees
8 Jun - 9 Jun
HOT TUB~Dog Friendly Cabin~Fishing~River boat ramp~20 Min to Lake Cumberland
Exterior

Hot Tub & Firepit~Game Center~Lake Cumberland~Family Friendly~River Boat Ramp

Hot Tub & Firepit~Game Center~Lake Cumberland~Family Friendly~River Boat Ramp
Jamestown
10.0 out of 10, Exceptional, (5 reviews)
"The stay was very nice and peaceful "
United States
earl c.
The price is HK$1,009
HK$3,497 total
includes taxes & fees
14 Jun - 15 Jun
Hot Tub & Firepit~Game Center~Lake Cumberland~Family Friendly~River Boat Ramp
Beach

Unique Hexagon Cottage-Above J'town Marina-Boat Parking-3 En Suite Baths-Pets OK

Unique Hexagon Cottage-Above J'town Marina-Boat Parking-3 En Suite Baths-Pets OK
Jamestown
10.0 out of 10, Exceptional, (202 reviews)
"Everything was great "
United States
John W.
The price is HK$1,234
HK$3,184 total
includes taxes & fees
5 Jun - 6 Jun
Unique Hexagon Cottage-Above J'town Marina-Boat Parking-3 En Suite Baths-Pets OK
Exterior

Cabin w/ River Boat Ramp~Private HotTub~Sauna~Lake Cumberland~Firepit~Pickleball

Cabin w/ River Boat Ramp~Private HotTub~Sauna~Lake Cumberland~Firepit~Pickleball
Jamestown
9.6 out of 10, Exceptional, (5 reviews)
"Yes the hot tub was great and very pet friendly. We loved the amenities! What a great stay. We will be back!! "
United States
Marina W.
The price is HK$1,307
HK$3,868 total
includes taxes & fees
14 Jun - 15 Jun
Cabin w/ River Boat Ramp~Private HotTub~Sauna~Lake Cumberland~Firepit~Pickleball
Exterior

Fishing~HotTub&Sauna~Pickleball~PingPong~Lake Cumberland~Playground~Firepit

Fishing~HotTub&Sauna~Pickleball~PingPong~Lake Cumberland~Playground~Firepit
Jamestown
10.0 out of 10, Exceptional, (2 reviews)
"Was perfect! Would absolutely stay again !"
United States
marsha w.
The price is HK$1,415
HK$4,005 total
includes taxes & fees
14 Jun - 15 Jun
Fishing~HotTub&Sauna~Pickleball~PingPong~Lake Cumberland~Playground~Firepit
Terrace/patio

New Rustic Home Near State Dock

New Rustic Home Near State Dock
Jamestown
10.0 out of 10, Exceptional, (8 reviews)
"This property is absolutely amazing so clean and easy to get to! "
United States
Bailee J.
The price is HK$1,411
HK$2,765 total
includes taxes & fees
1 Jun - 2 Jun
New Rustic Home Near State Dock
Exterior

Hot Tub~River Boat Ramp~Pickleball~Lake Cumberland~Family Friendly Cabin

Hot Tub~River Boat Ramp~Pickleball~Lake Cumberland~Family Friendly Cabin
Jamestown
9.0 out of 10, Wonderful, (2 reviews)
The price is HK$1,081
HK$3,585 total
includes taxes & fees
14 Jun - 15 Jun
Hot Tub~River Boat Ramp~Pickleball~Lake Cumberland~Family Friendly Cabin
Terrace/patio

Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.

Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
Jamestown
9.4 out of 10, Exceptional, (31 reviews)
"Great location, very comfortable, and pet friendly. We had friends at the campground behind the house, so it was great to walk over on the path in the back yard. We also checked out the state park and Lily Creek falls. Beautiful area!"
United States
Emily W.
The price is HK$1,567
HK$3,214 total
includes taxes & fees
1 Jun - 2 Jun
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
Marina

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

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Jamestown
9.8 out of 10, Exceptional, (26 reviews)
"Excellent place to stay."
United States
Jason E.
The price is HK$2,343
HK$4,432 total
includes taxes & fees
7 Jun - 8 Jun
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Fridge, microwave, oven, stovetop

Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
Jamestown
10.0 out of 10, Exceptional, (20 reviews)
"Amazing stay! House is very clean with lovely decor! Will stay here again for sure!!"
United States
Jennifer L.
The price is HK$1,270
HK$3,084 total
includes taxes & fees
1 Jun - 2 Jun
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
Fridge, microwave, oven, stovetop

The Lodge Lake Retreat – Family-Friendly with Private River Access

The Lodge Lake Retreat – Family-Friendly with Private River Access
Jamestown
10.0 out of 10, Exceptional, (1 review)
"Th place was extremely clean, check in was simple and easy, the listing was exactly as described. The sheets on the bed were amazing and the beds were comfortable "
United States
Dillon R.
The price is HK$784
HK$1,771 total
includes taxes & fees
1 Jun - 2 Jun
The Lodge Lake Retreat – Family-Friendly with Private River Access
Sports court

Lake Cumberland Condo Near State Park - Gated Community - Family Friendly

Lake Cumberland Condo Near State Park - Gated Community - Family Friendly
Jamestown
10.0 out of 10, Exceptional, (1 review)
"Great location! Kids love the pool"
United States
Jaime H.
The price is HK$1,411
HK$3,015 total
includes taxes & fees
2 Jun - 3 Jun
Lake Cumberland Condo Near State Park - Gated Community - Family Friendly
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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Top Jamestown Hotel Reviews

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

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

10/10 Excellent
"Cleanest refrigerator we have ever had. Everything was as advertised. Our weekend was extremely rainy so we put a tarp on the upper deck so we could set outside when it rained on the lower deck."
Larry B. 5-night trip
Posted 3 days ago
Sunset Ridge-Sleeps 16-Panoramic Lake Cumberland Views-3 Decks-Jamestown Marina

Find out more about Jamestown

Search for holiday rentals in Jamestown on Expedia! You can easily find your home rentals, villas, holiday apartments in Jamestown using one of the methods below:

  • View our selection of featured holiday rentals in Jamestown
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  • Enter your travel dates to view the best deals on holiday rentals in Jamestown while they last

Look no further and take a look at our great range of rental properties in Jamestown!

Frequently asked questions

Can I find holiday rentals in Jamestown?

Yes, there are holiday rentals close to the most popular sights in Jamestown, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Jamestown speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the waterfront and parks during your trip.

What are some of the best holiday rentals that Jamestown has to offer?

Sunset Ridge-Sleeps 16-Panoramic Lake Cumberland Views-3 Decks-Jamestown Marina: This highly rated holiday home rental in Jamestown is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Another good choice for your trip to Jamestown is Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!.

How many holiday rentals are there in Jamestown?

With 41 Expedia holiday rentals, you're guaranteed to find just the right place for your Jamestown stay.

What’s there to see and do in Jamestown?

Lake Cumberland State Resort Park and Wolf Creek National Fish Hatchery are a couple of lovely local spots to get outside and enjoy nature. While here, Jamestown Marina and Cumberland River are other places worth a visit.

What’s a holiday rental in Jamestown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Jamestown. Holiday rentals provide amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.