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

Jamestown Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Jamestown holiday rentals

1. New Near Jamestown Dock - A

New Near Jamestown Dock - A
Jamestown
9.6 out of 10, Exceptional, (27 reviews)
"The place was perfect for what we needed. It's right next to Pepe's and Giovanni's, two of my favorite Cumberland restaurants. It was also just 22 minutes from State Park Marina. You can hear everything from every room; we all went to bed and woke up at the same time, so it didn't bother us. I also loved the AC units in each room."
United States
Jennifer
The price is NZ$349
includes taxes & fees
6 Sept - 7 Sept
New Near Jamestown Dock - A

2. 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 NZ$319
includes taxes & fees
7 Sept - 8 Sept
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky

3. 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, (215 reviews)
"We felt like we were at home! Very clean and comfortable home with everything we needed. Communication with the host was flawless. This was my families first trip to Lake Cumberland and it was everything we thought it would be. Beautiful lake! We will definitely be coming back and staying at the Hexagon cottage again."
United States
Joleen
The price is NZ$680
includes taxes & fees
23 Sept - 24 Sept
Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay

4. 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, (19 reviews)
"Such a lovely property. Very cozy and inviting. We will definitely stay again."
United States
Jennifer S.
The price is NZ$593
includes taxes & fees
7 Sept - 8 Sept
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build

5. 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 NZ$604
includes taxes & fees
7 Sept - 8 Sept
Hot Tub~Firepit~Riverfront~Near Lake Cumberland

6. Cozy Lake Time Retreat

Cozy Lake Time Retreat
Jamestown
10.0 out of 10, Exceptional, (2 reviews)
"Nice little place."
United States
Brandon J.
The price is NZ$455
includes taxes & fees
7 Sept - 8 Sept
Cozy Lake Time Retreat

7. 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, (13 reviews)
"Great place "
United States
Melissa B.
The price is NZ$680
includes taxes & fees
8 Sept - 9 Sept
Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!

8. 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, (21 reviews)
"Amazing stay! House is very clean with lovely decor! Will stay here again for sure!!"
United States
Jennifer L.
The price is NZ$667
includes taxes & fees
7 Sept - 8 Sept
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

9. 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 NZ$695
includes taxes & fees
7 Sept - 8 Sept
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.

10. New Rustic Home Near State Dock

New Rustic Home Near State Dock
Jamestown
9.8 out of 10, Exceptional, (12 reviews)
"Have driven past many times and was excited to stay here!"
United States
Ashley D.
The price is NZ$581
includes taxes & fees
15 Sept - 16 Sept
New Rustic Home Near State Dock

11. 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, (4 reviews)
"Nice place with boat ramp."
United States
Josh S.
The price is NZ$571
includes taxes & fees
16 Sept - 17 Sept
Cabin w/ Firepit~Pickleball~Arcade Games~River Boat Ramp~20 Min Lake Cumberland

12. 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 NZ$581
includes taxes & fees
7 Sept - 8 Sept
HOT TUB~Dog Friendly Cabin~Fishing~River boat ramp~20 Min to Lake Cumberland

13. B - New near Jamestown Dock

B - New near Jamestown Dock
Jamestown
9.6 out of 10, Exceptional, (26 reviews)
"Great place to stay, property is very well maintained. Ample parking for truck and boat, highly recommend, will stay here again. "
United States
Trent N.
The price is NZ$350
includes taxes & fees
8 Sept - 9 Sept
B - New near Jamestown Dock

14. 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 NZ$793
includes taxes & fees
15 Sept - 16 Sept
Great place to gather near Lake Cumberland

15. Sunset Ridge·Sleeps 16·Panoramic Lake Cumberland Views·3 Decks·Jamestown Marina

Sunset Ridge·Sleeps 16·Panoramic Lake Cumberland Views·3 Decks·Jamestown Marina
Jamestown
10.0 out of 10, Exceptional, (181 reviews)
"Place was clean & lots of amenities. Beautiful view."
United States
Rachael B.
The price is NZ$1,155
includes taxes & fees
9 Sept - 10 Sept
Sunset Ridge·Sleeps 16·Panoramic Lake Cumberland Views·3 Decks·Jamestown Marina

16. 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
9.8 out of 10, Exceptional, (18 reviews)
"Wonderful place to stay for a few days on the lake with family. "
United States
Lena R.
The price is NZ$851
includes taxes & fees
8 Sept - 9 Sept
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

17. 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 NZ$578
includes taxes & fees
8 Sept - 9 Sept
Riverfront View~Boat Ramp~Foosball~Family Friendly Cabin~20 Min Lake Cumberland

18. 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 NZ$571
includes taxes & fees
16 Sept - 17 Sept
Riverfront~Firepit~Fishing~20 Min Lake Cumberland~Game Table

19. 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.
Fishing~HotTub&Sauna~Pickleball~PingPong~Lake Cumberland~Playground~Firepit

20. 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 NZ$583
includes taxes & fees
7 Sept - 8 Sept
Cabin w/ River Boat Ramp~Private HotTub~Sauna~Lake Cumberland~Firepit~Pickleball
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Jamestown Hotel Reviews

Find out more about Jamestown

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Jamestown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Jamestown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Jamestown. Seeing all the best attractions is bound to make you fall in love with Jamestown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Jamestown short-term rentals, that won’t be hard to do.

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.