Jamestown Holiday Rentals

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Holiday Rentals in Jamestown

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

9.8 out of 10, Exceptional, (27)
"Great location. Great place, beautiful views"
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

10.0 out of 10, Exceptional, (31)
"I can’t stress enough how BEAUTIFUL the view is from both inside(huge windows) and outside(2 levels of deck viewing & seating)! Wonderfully decorated, and super comfy furnishings. Definitely recommend, and will be back! "
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

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

9.8 out of 10, Exceptional, (10)
"Cute--3 Bedroom/1 Bath stand alone building/cabin with hot tub--pet friendly! Clean + Had all the amenities needed for a weekend stay (or longer if need be). We had a great time by the firepit and using the hot tub. There was also cards and several board games to play. In a quiet neighborhood. Check in process was easy. Though located above the marina--was not walking distance --property does not overlook the lake or have steps leading down to the lake (unsure if there was a public access...
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Secluded Jamestown Cabin w/ Fire Pit!

4.0 out of 10, (2)
"The house is very cute and has a great view of the lake from the deck. I will note that during some very heavy rainfall over the weekend, one of the windows to the deck began leaking heavily and soaked the small rug. We spent the length of two storms constantly wringing out towels to keep the leak from spreading into the carpet. Otherwise we enjoyed the stay."
Secluded Jamestown Cabin w/ Fire Pit!

New cabin sleeps 6 only 3mi from Jamestown Dock + Outdoor fun!

10.0 out of 10, Exceptional, (10)
"The perfect getaway weekend with some friends at the lake!! The host was super communicable and friendly. He made sure everything was perfect and ready to go for us for the weekend. I hope to stay again if I have another lake weekend trip!"
The price is NZ$342
includes taxes & fees
24 Nov - 25 Nov
New cabin sleeps 6 only 3mi from Jamestown Dock + Outdoor fun!

Ultimate Getaway Lake Cumberland, Great Location, easy access to water

9.2 out of 10, Wonderful, (139)
" …"
Ultimate Getaway Lake Cumberland, Great Location, easy access to water

Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!

9.8 out of 10, Exceptional, (64)
"Recommend, cool place close to Marina"
Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!

Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!!

10.0 out of 10, Exceptional, (19)
"Will definitely stay here again "
Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!!

Harbor Hilltop at Cumberland

9.8 out of 10, Exceptional, (10)
"This was a girls weekend "
The price is NZ$703
includes taxes & fees
24 Nov - 25 Nov
Harbor Hilltop at Cumberland

Lake Cumberland Retreat w/ Deck & Views!

9.2 out of 10, Wonderful, (11)
"House was very clean and just as pictures show. Very quiet spot but still close to the boat ramp and town for coffee, groceries, fuel, etc. Host was very responsive before and during especially being flexible with check in/out times. Excellent AC was much appreciated in the heat. Plenty of rooms and bathrooms spread out for our large group, never ran out of hot water. Made good use of the main floor and downstairs sitting areas with a great setup downstairs with kitchenette, couches and large TV...
Lake Cumberland Retreat w/ Deck & Views!

Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!! -#2

10.0 out of 10, Exceptional, (14)
"Cottage is right outside of Jamestown KY. You are close to lake Cumberland and also close to Jamestown. Cottage is beautiful and very spacious. Cottage comes with everything you could need during your stay. We will definitely be back! "
Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!! -#2

Cumberland River Cabin Rental

10.0 out of 10, Exceptional, (276)
"Three guys down for a fishing trip. The house and property were great. Being right on the river with ramp access was relaxing and convenient. "
Cumberland River Cabin Rental

Kozy Haven Log Cabin Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"Beautiful cabin! "
The price is NZ$219
includes taxes & fees
6 Dec - 7 Dec
Kozy Haven Log Cabin Rentals

Private Catch And Release Lake--Boat Rental Included! Close to Lake Cumberland!

10.0 out of 10, Exceptional, (225)
"It was a great time and a great place. "
Private Catch And Release Lake--Boat Rental Included! Close to Lake Cumberland!

This charming cozy cottage has a private hot tub, deck for fishing.

9.8 out of 10, Exceptional, (142)
"Was a great stay. Nice place, deck over a pond. Owner was great communication. highly recommend."
This charming cozy cottage has a private hot tub, deck for fishing.

Cozy Cabin - Lake Cumberland - Hot Tub

9.6 out of 10, Exceptional, (18)
"Perfect for a quiet getaway, hot tub was great, Fall scenery was awesome, view of the lake, quiet, secluded and private, close to restaurants and marinas, cabin was cozy, nice size for a couple or small family."
Cozy Cabin - Lake Cumberland - Hot Tub

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

9.8 out of 10, Exceptional, (19)
"Overall we enjoyed our stay here, bummed that the pool was not open as it showed in the description of the house and was the main reason for choosing the location. If it is closed for the season, list it as such. The view is great! "
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍

Lake Front Home with community boat ramp. Private, close to marinas and town.

9.6 out of 10, Exceptional, (214)
"We enjoyed our stay at this cute cabin with a great view located close to town. The hosts were excellent at communication and responded quickly. The deck is the focal point and is great for sitting out and admiring the water, enjoying an evening fire or cooking out dinner. My only complaint is in sleeping comfort. The bed in the main bedroom was so hard the first night that we switched to the other bedroom the second night. In that room, the bed was much better, but the window blind is too small...
Lake Front Home with community boat ramp. Private, close to marinas and town.

Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!

10.0 out of 10, Exceptional, (104)
"We enjoyed sitting on the screened-in patio overlooking the river watching the falling leaves float to the ground. Watched a group of 15 wild turkeys make the way way past the property. their wwa"
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!

Perfect Lake House on Lake Cumberland

10.0 out of 10, Exceptional, (6)
"We enjoyed our stay. The house was beautiful and well equipped. Enjoyed the pool table and air hockey downstairs. We would definitely stay again!!"
Perfect Lake House on Lake Cumberland
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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Other types of properties in Jamestown you may be interested in

Lake Cumberland State Resort Park

3.0 star property
8.8 out of 10, Excellent, (427)
"Needs to be updated. Area was quiet and nice. "
The price is NZ$179
includes taxes & fees
6 Dec - 7 Dec
Lake Cumberland State Resort Park

NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

10.0 out of 10, Exceptional, (31)
"I can’t stress enough how BEAUTIFUL the view is from both inside(huge windows) and outside(2 levels of deck viewing & seating)! Wonderfully decorated, and super comfy furnishings. Definitely recommend, and will be back! "
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

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

9.8 out of 10, Exceptional, (10)
"Cute--3 Bedroom/1 Bath stand alone building/cabin with hot tub--pet friendly! Clean + Had all the amenities needed for a weekend stay (or longer if need be). We had a great time by the firepit and using the hot tub. There was also cards and several board games to play. In a quiet neighborhood. Check in process was easy. Though located above the marina--was not walking distance --property does not overlook the lake or have steps leading down to the lake (unsure if there was a public access...
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!: This highly rated holiday home rental in Jamestown is located on a lake, and has a fireplace, a furnished patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Jamestown?

With 32 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 Cumberland River are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Wolf Creek National Fish Hatchery and Lindsey Wilson College.

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.