An aerial view of a coastal area with a lighthouse, a parking lot, and a rocky shoreline.

Jamestown Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Jamestown holiday rentals

Smart TV, fireplace

B - New near Jamestown Dock

B - New near Jamestown Dock
Jamestown
9.6 out of 10, Exceptional, (22 reviews)
"This is a great place to stay and the location is perfect!"
United States
Crystal S.
The price is HK$706
HK$1,616 total
includes taxes & fees
30 Jul - 31 Jul
B - New near Jamestown Dock
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
9.4 out of 10, Exceptional, (17 reviews)
"Such a lovely property. Very cozy and inviting. We will definitely stay again."
United States
Jennifer S.
The price is HK$931
HK$2,880 total
includes taxes & fees
18 Aug - 19 Aug
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
Smart TV, fireplace

Hot Tub~Firepit~Riverfront~Near Lake Cumberland

Hot Tub~Firepit~Riverfront~Near Lake Cumberland
Jamestown
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and quiet. The beds were comfortable and the house was stocked with nice touches like laundry pods and coffee. I would definitely stay there again!"
United States
Christine V.
The price is HK$889
HK$2,816 total
includes taxes & fees
10 Aug - 11 Aug
Hot Tub~Firepit~Riverfront~Near 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, (6 reviews)
"The stay was very nice and peaceful "
United States
earl c.
The price is HK$754
HK$2,675 total
includes taxes & fees
18 Aug - 19 Aug
Hot Tub & Firepit~Game Center~Lake Cumberland~Family Friendly~River Boat Ramp
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, (13 reviews)
"Great location."
United States
Donald S.
The price is HK$875
HK$1,596 total
includes taxes & fees
21 Jul - 22 Jul
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$762
HK$2,685 total
includes taxes & fees
18 Aug - 19 Aug
Cabin w/ Firepit~Pickleball~Arcade Games~River Boat Ramp~20 Min Lake Cumberland
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$804
HK$2,740 total
includes taxes & fees
18 Aug - 19 Aug
HOT TUB~Dog Friendly Cabin~Fishing~River boat ramp~20 Min to Lake Cumberland
Exterior

Riverfront View~Boat Ramp~Foosball~Family Friendly Cabin~20 Min Lake Cumberland

Riverfront View~Boat Ramp~Foosball~Family Friendly Cabin~20 Min Lake Cumberland
Jamestown
10.0 out of 10, Exceptional, (1 review)
"Place was amazing, right on the river. Was able to walk right down and caught some trout. Check in was easy. Place was clean and as described. "
United States
Jered C.
The price is HK$762
HK$2,685 total
includes taxes & fees
18 Aug - 19 Aug
Riverfront View~Boat Ramp~Foosball~Family Friendly Cabin~20 Min Lake Cumberland
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$804
HK$2,740 total
includes taxes & fees
18 Aug - 19 Aug
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$813
HK$2,740 total
includes taxes & fees
17 Aug - 18 Aug
Fishing~HotTub&Sauna~Pickleball~PingPong~Lake Cumberland~Playground~Firepit
Property grounds

Riverfront~Firepit~Fishing~20 Min Lake Cumberland~Game Table

Riverfront~Firepit~Fishing~20 Min Lake Cumberland~Game Table
Jamestown
10.0 out of 10, Exceptional, (1 review)
"Great location with river and very clean. Please note this is shared 3 units and not a stand alone unit like the rest. Needs a new coffee maker and a small skillet but otherwise very well stocked"
United States
Anonymous traveller
The price is HK$762
HK$2,685 total
includes taxes & fees
18 Aug - 19 Aug
Riverfront~Firepit~Fishing~20 Min Lake Cumberland~Game Table
Coffee/tea maker, fridge, microwave, oven

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, (3 reviews)
"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$972
HK$2,066 total
includes taxes & fees
23 Jul - 24 Jul
The Lodge Lake Retreat – Family-Friendly with Private River Access
Interior

Cozy Lake Time Retreat

Cozy Lake Time Retreat
Jamestown
10.0 out of 10, Exceptional, (1 review)
"Beautiful house. Everything was an extremely wonderful stay. Only note of caution if you pull a boat watch getting in the driveway motor drug a little but was able to pull across the road and raise motor and got in just fine."
United States
Matthew G.
The price is HK$882
HK$2,105 total
includes taxes & fees
20 Jul - 21 Jul
Cozy Lake Time Retreat
Beach

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
10.0 out of 10, Exceptional, (210 reviews)
"It was a great place to stay, close to the town of Jamestown and the Marina!Enjoyed the nights by the fire and having a pool table was a plus!"
United States
Crystal C.
Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay
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$804
HK$2,740 total
includes taxes & fees
18 Aug - 19 Aug
Hot Tub~River Boat Ramp~Pickleball~Lake Cumberland~Family Friendly Cabin
Interior

Great place to gather near Lake Cumberland

Great place to gather near Lake Cumberland
Jamestown
10.0 out of 10, Exceptional, (10 reviews)
"Very clean, large & spacious rooms comfortable for us and our friends to stay."
United States
Melissa M.
The price is HK$1,764
HK$3,708 total
includes taxes & fees
25 Jul - 26 Jul
Great place to gather near Lake Cumberland
Terrace/patio

Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!

Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!
Jamestown
9.4 out of 10, Exceptional, (11 reviews)
"Great place "
United States
Melissa B.
The price is HK$1,304
HK$3,324 total
includes taxes & fees
18 Aug - 19 Aug
Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!
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$2,766 total
includes taxes & fees
26 Jul - 27 Jul
New Rustic Home Near State Dock
Coffee/tea maker, fridge, microwave, oven

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$3,086 total
includes taxes & fees
22 Jul - 23 Jul
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
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$1,568
HK$3,215 total
includes taxes & fees
20 Jul - 21 Jul
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
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

Family friendly 2-bedroom lake getaway in serene Jamestown with pool

Family friendly 2-bedroom lake getaway in serene Jamestown with pool

10/10 Excellent
"We really enjoyed our stay at this little condominium. It was equipped with everything you need, and it had close access to the lake. The amenities were a plus. Tiffany was easy to communicate with. I recommend to anyone."
Margaret C. 2-night trip
Posted 5 hours ago
Family friendly 2-bedroom lake getaway in serene Jamestown with pool

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
  • Use the map to find apartments and other holiday homes in the Jamestown neighbourhood you prefer
  • 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.

How many holiday rentals are there in Jamestown?

With 44 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.