Jamestown Holiday Rentals

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Check prices for these dates

Tonight
11 Nov - 12 Nov
Tomorrow
12 Nov - 13 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

Holiday Rentals in Jamestown

Fridge, microwave, oven, stovetop
Cumberland River School House

Cumberland River School House

Jamestown
The price is HK$1,244
HK$2,796 total
includes taxes & fees
12 Nov - 13 Nov
Cumberland River School House
Fridge, microwave, oven, stovetop
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

2.0 star property
Jamestown
9.4 out of 10, Exceptional, (13)
"This is a beautiful place to stay with tons of amenities. We loved the cabin I do wish it was a different location though but they really can’t help that! We had a great experience and I hope to return one day."
United States
Olivia L.
The price is HK$789
HK$2,756 total
includes taxes & fees
17 Nov - 18 Nov
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
Dining
New Near Jamestown Dock - A

New Near Jamestown Dock - A

Jamestown
9.8 out of 10, Exceptional, (22)
"Nice property with unique setup. Convenient location."
United States
Robert M.
The price is HK$777
HK$1,697 total
includes taxes & fees
12 Nov - 13 Nov
New Near Jamestown Dock - A
Fridge, microwave, oven, stovetop
Historic Union Chapel School-Two Room, near Cumberland River & Lake Cumberland

Historic Union Chapel School-Two Room, near Cumberland River & Lake Cumberland

Jamestown
10.0 out of 10, Exceptional, (52)
"Very nice renovation, on the school, it’s more like a hotel stay with kitchen being outside of rooms and sharing with others but had everything you would want, will definitely stay there again if we are in the area!.."
United States
Anonymous traveller
The price is HK$972
HK$1,243 total
includes taxes & fees
14 Nov - 15 Nov
Historic Union Chapel School-Two Room, near Cumberland River & Lake Cumberland
Exterior detail
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, (5)
"It was great!"
United States
Jennifer W.
The price is HK$525
HK$1,178 total
includes taxes & fees
12 Nov - 13 Nov
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Terrace/patio
Guest Favorite! Super Clean! Close to Everything!

Guest Favorite! Super Clean! Close to Everything!

Jamestown
10.0 out of 10, Exceptional, (9)
"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$833
HK$1,861 total
includes taxes & fees
12 Nov - 13 Nov
Guest Favorite! Super Clean! Close to Everything!
Property grounds
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.

Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.

Jamestown
10.0 out of 10, Exceptional, (192)
"Overall we had a nice stay here. The extra driveway made it easy to park our boat which was a big reason for picking this property. The road is a bit narrow, so go slow. "
United States
Ben M.
The price is HK$896
HK$2,504 total
includes taxes & fees
25 Nov - 26 Nov
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.
Exterior
Lake house. Less than 3 miles from beautiful Lake Cumberland.

Lake house. Less than 3 miles from beautiful Lake Cumberland.

Jamestown
9.4 out of 10, Exceptional, (26)
"Great little place, close to town. Very clean place and host was amazing and very accommodating "
United States
mike v.
The price is HK$840
HK$1,920 total
includes taxes & fees
12 Nov - 13 Nov
Lake house. Less than 3 miles from beautiful 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, (2)
"Wanted a place close to the river and a boat ramp Great place highly recommend"
United States
doug c.
The price is HK$710
HK$2,660 total
includes taxes & fees
19 Nov - 20 Nov
HOT TUB~Dog Friendly Cabin~Fishing~River boat ramp~20 Min to Lake Cumberland
Exterior
River Boat Ramp~Private HotTub~Lake Cumberland~Firepit~Pickleball~Playground

River Boat Ramp~Private HotTub~Lake Cumberland~Firepit~Pickleball~Playground

Jamestown
10.0 out of 10, Exceptional, (2)
"Very nice place. Lots of things for everyone. "
United States
Dona R.
The price is HK$710
HK$2,660 total
includes taxes & fees
18 Nov - 19 Nov
River Boat Ramp~Private HotTub~Lake Cumberland~Firepit~Pickleball~Playground
Exterior
Hot Tub & Firepit~20 Min Lake Cumberland~Family Friendly~River Boat Ramp

Hot Tub & Firepit~20 Min Lake Cumberland~Family Friendly~River Boat Ramp

Jamestown
10.0 out of 10, Exceptional, (4)
"This has been our second stay here. What a beautiful cabin and very peaceful. Our little dog enjoys our visits here as well. The cabin is very clean and very accommodating! We love sitting on the front porch in the morning and after supper. We enjoyed the hot tub which has great privacy! The beds are very comfortable!!! The host “Stephanie “ is very kind and makes sure you have a great stay! It’s our favorite place to stay in Kentucky!"
United States
Fonda L.
The price is HK$725
HK$2,676 total
includes taxes & fees
18 Nov - 19 Nov
Hot Tub & Firepit~20 Min Lake Cumberland~Family Friendly~River Boat Ramp
Exterior
Cabin with Firepit~Arcade Games~River Boat Ramp~20 Min Lake Cumberland

Cabin with Firepit~Arcade Games~River Boat Ramp~20 Min Lake Cumberland

Jamestown
10.0 out of 10, Exceptional, (3)
"River sitting was Great "
United States
william c.
The price is HK$772
HK$2,737 total
includes taxes & fees
12 Nov - 13 Nov
Cabin with Firepit~Arcade Games~River Boat Ramp~20 Min Lake Cumberland
Outdoor dining
Cozy 2-bedroom, 1.5 bath RV with outdoor kitchen, 3.5 miles from Wolf Creek Dam

Cozy 2-bedroom, 1.5 bath RV with outdoor kitchen, 3.5 miles from Wolf Creek Dam

Jamestown
10.0 out of 10, Exceptional, (3)
"Easy check in! 10 minutes from State Dock! Lister was very helpful!"
United States
Jesse T.
The price is HK$777
HK$1,474 total
includes taxes & fees
18 Nov - 19 Nov
Cozy 2-bedroom, 1.5 bath RV with outdoor kitchen, 3.5 miles from Wolf Creek Dam
Exterior
Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!

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

Jamestown
10.0 out of 10, Exceptional, (9)
"We absolutely loved this little cabin. It was a nice Father's Day getaway for our family. We had so much fun."
United States
Ellen C.
The price is HK$940
HK$2,948 total
includes taxes & fees
12 Nov - 13 Nov
Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!
Smart TV
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, (29)
"Cozy place and close to the marina where we wanted to fish and explore on Lake Cumberland."
United States
Lesia C.
The price is HK$1,555
HK$3,188 total
includes taxes & fees
12 Nov - 13 Nov
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)
"Everything we needed for a fun, relaxing lake weekend! House was clean and fully stocked. The cute coffee bar, extra towels, and kids’ games were a bonus! The host was incredibly friendly and responsive. Room to park our 24’ boat and a 5 min drive to Jamestown marina. Highly recommend booking. "
United States
Anna H.
The price is HK$1,244
HK$3,042 total
includes taxes & fees
14 Nov - 15 Nov
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Property grounds
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
10.0 out of 10, Exceptional, (13)
"Great experience, very cute home. Would love to visit again! "
United States
Adam F.
The price is HK$1,547
HK$3,419 total
includes taxes & fees
22 Nov - 23 Nov
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
Exterior
Fishing~HotTub~Pickleball~20 Min Lake Cumberland~Playground~Firepit

Fishing~HotTub~Pickleball~20 Min Lake Cumberland~Playground~Firepit

Jamestown
10.0 out of 10, Exceptional, (1)
"Great little neighborhood of cabins. Very clean and comfortable. The owners thought of the little details, extra toothbrushes, q tips etc, even hair ties! Nice quality shampoo and conditioner plus body wash available. Plenty of paper products, cleaning supplies, laundry products, even aluminum foil and ziplock baggies!Our grandkids enjoyed the playground after a day on the lake. The hot tub was very relaxing. The cabin is tastefully decorated and has updated furnishings and appliances plus...
United States
Jami D.
The price is HK$763
HK$2,710 total
includes taxes & fees
20 Nov - 21 Nov
Fishing~HotTub~Pickleball~20 Min Lake Cumberland~Playground~Firepit
2 bedrooms, WiFi, bed sheets
Family friendly 2-bedroom lake getaway in serene Jamestown with pool

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

2.0 star property
Jamestown
The price is HK$746
HK$1,208 total
includes taxes & fees
12 Nov - 13 Nov
Family friendly 2-bedroom lake getaway in serene Jamestown with pool
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, (19)
"Amazing stay! House is very clean with lovely decor! Will stay here again for sure!!"
United States
Jennifer L.
The price is HK$1,259
HK$3,059 total
includes taxes & fees
15 Nov - 16 Nov
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
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

Timber Pointe Resort

Timber Pointe Resort

10/10 Excellent
"Quiet, clean affordable "
Tammy 1-night trip
Posted 1 day ago
Timber Pointe Resort

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?

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.: 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. Some other top choices in Jamestown are Luxe Lake Cumberland Retreat w/ Decks on 1 Acre! and Charming 5-bedroom/3-bath home with easy access to Lake Cumberland.

How many holiday rentals are there in Jamestown?

With 37 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.