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Jamestown Holiday Rentals

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Check prices for these dates

Tonight
3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Holiday Rentals in Jamestown

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

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

Jamestown
10.0 out of 10, Exceptional, (155)
"Check in was very easy, beautiful home,views were pretty,overall great family time!"
United States
paige m.
The price is HK$1,697
HK$4,497 total
includes taxes & fees
23 Dec - 24 Dec
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
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)
"The house was great! Clean, convenient and very quiet. We would definitely stay again!! "
United States
Toby E.
The price is HK$1,245
HK$3,029 total
includes taxes & fees
12 Dec - 13 Dec
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 place to stay by the lake!"
United States
Grant B.
The price is HK$1,549
HK$3,424 total
includes taxes & fees
4 Jan - 5 Jan 2026
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
Interior
Apple Valley Comfy “Treehouse" 2-Bedroom Condo inside Lake Cumberland State Park

Apple Valley Comfy “Treehouse" 2-Bedroom Condo inside Lake Cumberland State Park

4.0 star property
Jamestown
9.8 out of 10, Exceptional, (64)
"We had a wonderful time! Beautiful condo! "
United States
Shannon K.
Apple Valley Comfy “Treehouse" 2-Bedroom Condo inside Lake Cumberland State Park
Property grounds
Cumberland Get-A-Way located at entrance of State Park

Cumberland Get-A-Way located at entrance of State Park

Jamestown
10.0 out of 10, Exceptional, (19)
"Thanks Landon we had a great stay and the house was great!!! "
United States
Sally J.
Cumberland Get-A-Way located at entrance of State Park
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, (193)
"Great property, clean and as advertised! Would definitely stay here again. Had an issue with the grill one night, fluke thing, owner took care of next day! Great place to stay!"
United States
DOUGLAS M.
The price is HK$1,037
HK$2,679 total
includes taxes & fees
14 Dec - 15 Dec
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.
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)
"5 stars!"
United States
Lisa W.
The price is HK$711
HK$2,663 total
includes taxes & fees
11 Dec - 12 Dec
HOT TUB~Dog Friendly Cabin~Fishing~River boat ramp~20 Min to Lake Cumberland
Fridge, microwave, oven, stovetop
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland

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

Jamestown
9.6 out of 10, Exceptional, (5)
"Jenn was super responsive and gave us plenty of info on fishing/boating access in the area. The house was a great size with a cute unique layout. Huge deck for plenty of outside hang time and close to a boat ramp to easily drop my canoe in. Just a few minutes from the State Park too! "
United States
Joe P.
The price is HK$1,822
HK$3,767 total
includes taxes & fees
5 Dec - 6 Dec
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland
Interior
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
10.0 out of 10, Exceptional, (53)
"Great location and as advertised. "
United States
Mike G.
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
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$1,261
HK$3,063 total
includes taxes & fees
7 Dec - 8 Dec
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
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$790
HK$2,759 total
includes taxes & fees
7 Dec - 8 Dec
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
3 bedrooms, free WiFi, bed sheets
3 Bed Log Cabin Located 0.5 miles from Safe Harbor Jamestown #302

3 Bed Log Cabin Located 0.5 miles from Safe Harbor Jamestown #302

Jamestown
7.8 out of 10, Good, (9)
"This cabin is cozy and comfortable. Very clean. The kids loved the loft area where they slept and it's close to everything in Jamestown. "
United States
Nick B.
3 Bed Log Cabin Located 0.5 miles from Safe Harbor Jamestown #302
TV
Lakeside 3 bedroom chalet with hot tub!!

Lakeside 3 bedroom chalet with hot tub!!

Byrdstown
9.0 out of 10, Wonderful, (8)
"Nice"
United States
William B.
Lakeside 3 bedroom chalet with hot tub!!
Outdoor spa tub
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

Monticello
9.8 out of 10, Exceptional, (32)
"Perfect for a large family. The house and pool are great and the view is amazing! "
United States
MARY BETH K.
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
Premium bedding, individually decorated, individually furnished
Kozy Haven Log Cabin Rentals

Kozy Haven Log Cabin Rentals

3.0 star property
Columbia
9.6 out of 10, Exceptional, (43)
"Very peaceful, quiet, and private and clean place to stay"
United States
Michelle
The price is HK$848
HK$1,264 total
includes taxes & fees
5 Dec - 6 Dec
Kozy Haven Log Cabin Rentals
Exterior
Perfect Lake House on Lake Cumberland

Perfect Lake House on Lake Cumberland

Somerset
10.0 out of 10, Exceptional, (11)
"Great property, close to everything. Would stay again "
United States
Stephen B.
Perfect Lake House on Lake Cumberland
Property grounds
Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings

Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings

Nancy
9.6 out of 10, Exceptional, (183)
"We loved our stay at this property! Nice location, quiet, relaxing, pretty views, everything there that we needed, and great memories made. Definitely recommend this rental!"
United States
Kara K.
Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings
Fridge, microwave, oven, stovetop
Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

Monticello
9.8 out of 10, Exceptional, (63)
"Good place to stay. Plenty of space for our family. Property is managed well. Pool was superb. Location great for boating activity on the Cumberland River/Lake."
United States
Sharon D.
Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.
Outdoor spa tub
Beautiful 6 Bedroom Cabin with Hot Tub and a Lakeview of Dale Hollow Lake #12

Beautiful 6 Bedroom Cabin with Hot Tub and a Lakeview of Dale Hollow Lake #12

Byrdstown
6.0 out of 10, (1)
"Cabin was outdated and really not made for 12 people. Not enough space in living room or kitchen. Enjoyed the view. "
United States
Diana P.
Beautiful 6 Bedroom Cabin with Hot Tub and a Lakeview of Dale Hollow Lake #12
Fridge, microwave, oven, stovetop
Joy On The Lake · Cumberland Canvas: Lake View, Fire Pit & Game Room

Joy On The Lake · Cumberland Canvas: Lake View, Fire Pit & Game Room

Somerset
10.0 out of 10, Exceptional, (15)
"It was a wonderful stay. Beautiful view!"
United States
Vanessa C.
The price is HK$1,096
HK$3,294 total
includes taxes & fees
16 Dec - 17 Dec
Joy On The Lake · Cumberland Canvas: Lake View, Fire Pit & Game Room
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

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

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

10/10 Excellent
"The host was very welcoming and provided lots of details prior to our stay. She made sure that everything was ready. We had a wonderful time and will definitely be booking this place again when we travel down to Kentucky again."
Katie V. 2-night trip
Posted 2 weeks ago
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

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, Cumberland River and Jamestown Marina 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.