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

Jamestown Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Jamestown vacation rentals

Dining

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 SAR 338
SAR 782 total
includes taxes & fees
17 Sep - 18 Sep
New Near Jamestown Dock - A
Smart TV, fireplace

2. 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 SAR 385
SAR 1,208 total
includes taxes & fees
20 Aug - 21 Aug
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
Smart TV, fireplace

3. 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 SAR 401
SAR 1,228 total
includes taxes & fees
1 Sep - 2 Sep
Hot Tub~Firepit~Riverfront~Near Lake Cumberland
Interior

4. 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 SAR 422
SAR 1,008 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Lake Time Retreat
Terrace/patio

5. 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 SAR 507
SAR 1,467 total
includes taxes & fees
20 Aug - 21 Aug
Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!
2 bedrooms, WiFi (free)

6. 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 SAR 514
SAR 930 total
includes taxes & fees
19 Aug - 20 Aug
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Coffee/tea maker, fridge, microwave, oven

7. 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)
"This is an awesome house…clean, nicely furnished, well equipped, close to the marina. Coming back in September."
United States
John S.
The price is SAR 608
SAR 1,478 total
includes taxes & fees
19 Aug - 20 Aug
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
Exterior

8. 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 SAR 332
SAR 1,147 total
includes taxes & fees
1 Sep - 2 Sep
Cabin w/ Firepit~Pickleball~Arcade Games~River Boat Ramp~20 Min Lake Cumberland
Outdoor spa tub

9. 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 SAR 361
SAR 1,179 total
includes taxes & fees
1 Sep - 2 Sep
HOT TUB~Dog Friendly Cabin~Fishing~River boat ramp~20 Min to Lake Cumberland
Exterior

10. 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, (7 reviews)
"The stay was very nice and peaceful "
United States
earl c.
The price is SAR 361
SAR 1,179 total
includes taxes & fees
1 Sep - 2 Sep
Hot Tub & Firepit~Game Center~Lake Cumberland~Family Friendly~River Boat Ramp
Terrace/patio

11. New Rustic Home Near State Dock

New Rustic Home Near State Dock
Jamestown
9.8 out of 10, Exceptional, (12 reviews)
"This was our 3rd time staying at the property. We absolutely love it!"
United States
Courtney W.
The price is SAR 676
SAR 1,312 total
includes taxes & fees
17 Sep - 18 Sep
New Rustic Home Near State Dock
Property grounds

12. 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 traveler
The price is SAR 332
SAR 1,147 total
includes taxes & fees
1 Sep - 2 Sep
Riverfront~Firepit~Fishing~20 Min Lake Cumberland~Game Table
Exterior

13. 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 SAR 332
SAR 1,147 total
includes taxes & fees
1 Sep - 2 Sep
Riverfront View~Boat Ramp~Foosball~Family Friendly Cabin~20 Min Lake Cumberland
Exterior

14. 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 SAR 361
SAR 1,179 total
includes taxes & fees
1 Sep - 2 Sep
Cabin w/ River Boat Ramp~Private HotTub~Sauna~Lake Cumberland~Firepit~Pickleball
Exterior

15. 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 SAR 361
SAR 1,179 total
includes taxes & fees
1 Sep - 2 Sep
Fishing~HotTub&Sauna~Pickleball~PingPong~Lake Cumberland~Playground~Firepit
Smart TV, fireplace

16. 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 SAR 338
SAR 782 total
includes taxes & fees
17 Sep - 18 Sep
B - New near Jamestown Dock
Exterior

17. Hot Tub~River Boat Ramp~Pickleball~Lake Cumberland~Family Friendly Cabin

Hot Tub~River Boat Ramp~Pickleball~Lake Cumberland~Family Friendly Cabin
Jamestown
9.6 out of 10, Exceptional, (4 reviews)
"Great place for kids"
United States
Devin S.
The price is SAR 361
SAR 1,179 total
includes taxes & fees
1 Sep - 2 Sep
Hot Tub~River Boat Ramp~Pickleball~Lake Cumberland~Family Friendly Cabin
Terrace/patio

18. 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 SAR 751
SAR 1,531 total
includes taxes & fees
20 Aug - 21 Aug
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
Interior

19. 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 SAR 845
SAR 1,763 total
includes taxes & fees
17 Sep - 18 Sep
Great place to gather near Lake Cumberland
Property grounds

20. Charming A-frame with Lake Cumberland Views

Charming A-frame with Lake Cumberland Views
Jamestown
7.0 out of 10, Good, (2 reviews)
"Very dated unit. One bath towel & one hand towel provided for 3 people. No local or network tv. Driv-way to unit was described as 4 wheel drive needed but walking down a most steep loose gravel drive with coolers, belongings, etc is dangerous for many. Very very overpriced unit. "
United States
Hank A.
The price is SAR 588
SAR 1,451 total
includes taxes & fees
19 Aug - 20 Aug
Charming A-frame with Lake Cumberland Views
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

Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

10/10 Excellent
"Great place for a nice Lake Cumberland getaway. The home was well equipped and very comfortable. The host was quick to answer questions and very nice. The location was really close to Safe Harbor Marina. We are looking forward to a return trip!"
Kimberly J. 4-night trip
Posted 7 hours ago
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

Frequently asked questions

Can I find vacation rentals in Jamestown?

Yes, we offer vacation rentals close to the most popular local attractions in Jamestown, or you can go with a more secluded option if you're looking for relaxation. 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 vacation rentals that Jamestown has to offer?

Sunset Ridge·Sleeps 16·Panoramic Lake Cumberland Views·3 Decks·Jamestown Marina: This highly rated vacation home rental in Jamestown is located on a lake and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind. Another good choice for your trip to Jamestown is Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!.

How many vacation rentals are there in Jamestown?

With 43 Expedia vacation rentals, you're sure 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 vacation rental in Jamestown like?

A vacation rental is a private property you can book for a couple of days or more in Jamestown. Vacation rentals feature amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for families.