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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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, (26 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 AED 331
AED 753 total
includes taxes & fees
8 Aug - 9 Aug
New Near Jamestown Dock - A
2 bedrooms, WiFi (free)

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 AED 455
AED 798 total
includes taxes & fees
9 Aug - 10 Aug
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Marina

3. 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, (29 reviews)
"Excellent place to stay."
United States
Jason E.
The price is AED 1,098
AED 2,077 total
includes taxes & fees
9 Aug - 10 Aug
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Terrace/patio

4. 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 AED 735
AED 1,506 total
includes taxes & fees
9 Aug - 10 Aug
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
Coffee/tea maker, fridge, microwave, oven

5. 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, (20 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 AED 595
AED 1,446 total
includes taxes & fees
13 Aug - 14 Aug
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
Interior

6. 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 AED 826
AED 1,737 total
includes taxes & fees
10 Aug - 11 Aug
Great place to gather near Lake Cumberland
Exterior detail

7. Restful Rustic Farmhouse on Lake Cumberland

Restful Rustic Farmhouse on Lake Cumberland
Jamestown
9.4 out of 10, Exceptional, (15 reviews)
"Our family had an amazing time at this vacation home! We had excellent communication with the owners and the place had everything we needed! Will definitely stay here again! Thank you for a wonderful holiday weekend!"
United States
Dana C.
The price is AED 1,546
AED 2,757 total
includes taxes & fees
1 Sep - 2 Sep
Restful Rustic Farmhouse on Lake Cumberland
Terrace/patio

8. 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, (11 reviews)
"Great place "
United States
Melissa B.
The price is AED 500
AED 1,439 total
includes taxes & fees
10 Aug - 11 Aug
Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!
Smart TV, fireplace

9. 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 AED 417
AED 1,331 total
includes taxes & fees
10 Aug - 11 Aug
Hot Tub~Firepit~Riverfront~Near Lake Cumberland
Terrace/patio

10. New Rustic Home Near State Dock

New Rustic Home Near State Dock
Jamestown
9.6 out of 10, Exceptional, (10 reviews)
"This property is absolutely amazing so clean and easy to get to! "
United States
Bailee J.
The price is AED 661
AED 1,296 total
includes taxes & fees
9 Aug - 10 Aug
New Rustic Home Near State Dock
Smart TV, fireplace

11. 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, (18 reviews)
"Such a lovely property. Very cozy and inviting. We will definitely stay again."
United States
Jennifer S.
The price is AED 424
AED 1,344 total
includes taxes & fees
2 Sep - 3 Sep
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
Coffee/tea maker, fridge, microwave, oven

12. 4BR Lake Cumberland Cabin - Hot Tub, Fire Pit, Near Boat Ramps, Pet Friendly

4BR Lake Cumberland Cabin - Hot Tub, Fire Pit, Near Boat Ramps, Pet Friendly
Jamestown
9.6 out of 10, Exceptional, (9 reviews)
"This house was beautiful and perfect for what we needed. "
United States
Shavona M.
The price is AED 911
AED 1,828 total
includes taxes & fees
25 Aug - 26 Aug
4BR Lake Cumberland Cabin - Hot Tub, Fire Pit, Near Boat Ramps, Pet Friendly
Outdoor dining

13. 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, (15 reviews)
"Wonderful place to stay for a few days on the lake with family. "
United States
Lena R.
The price is AED 915
AED 1,834 total
includes taxes & fees
1 Sep - 2 Sep
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
Interior

14. 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 AED 413
AED 970 total
includes taxes & fees
9 Aug - 10 Aug
Cozy Lake Time Retreat
Property grounds

15. 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 AED 549
AED 1,378 total
includes taxes & fees
12 Aug - 13 Aug
Charming A-frame with Lake Cumberland Views
Outdoor dining

16. "The Bee Hive" 1 mile from Lake Cumberland/Jamestown Marina

"The Bee Hive" 1 mile from Lake Cumberland/Jamestown Marina
Jamestown
8.0 out of 10, Very Good, (1 review)
"Ok place to stay."
United States
Olga H.
The price is AED 606
AED 1,435 total
includes taxes & fees
13 Aug - 14 Aug
"The Bee Hive" 1 mile from Lake Cumberland/Jamestown Marina
Exterior

17. Riverfront Cabin~Sleeps 18~Private River Boat Ramp~20 Min drive Lake Cumberland

Riverfront Cabin~Sleeps 18~Private River Boat Ramp~20 Min drive Lake Cumberland
Jamestown
10.0 out of 10, Exceptional, (3 reviews)
"Long weekend with my brothers, their wives, and our parents! Loved the time together, the space, the area, the river!Thank you Cabins on the Cumberland!"
United States
Melissa N.
The price is AED 1,587
AED 4,167 total
includes taxes & fees
18 Aug - 19 Aug
Riverfront Cabin~Sleeps 18~Private River Boat Ramp~20 Min drive Lake Cumberland
Coffee/tea maker, fridge, microwave, oven

18. The Lodge Lake Retreat – Family-Friendly with Private River Access

The Lodge Lake Retreat – Family-Friendly with Private River Access
Jamestown
10.0 out of 10, Exceptional, (4 reviews)
"Loved the place! New, clean house and spacious.Area was quiet and felt like we had the whole road to ourselves. Will definitely stay here again"
United States
Corey S.
The price is AED 455
AED 956 total
includes taxes & fees
9 Aug - 10 Aug
The Lodge Lake Retreat – Family-Friendly with Private River Access
Exterior

19. 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, (3 reviews)
"Nice place with boat ramp."
United States
Josh S.
The price is AED 353
AED 1,253 total
includes taxes & fees
10 Aug - 11 Aug
Cabin w/ Firepit~Pickleball~Arcade Games~River Boat Ramp~20 Min Lake Cumberland
Property grounds

20. 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 AED 325
AED 1,219 total
includes taxes & fees
10 Aug - 11 Aug
Riverfront~Firepit~Fishing~20 Min Lake Cumberland~Game Table
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

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

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

10/10 Excellent
"We had the best weekend! Perfect place for a fun family getaway!"
Amber W. 2-night trip
Posted 4 days ago
Sunset Ridge·Sleeps 16·Panoramic Lake Cumberland Views·3 Decks·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.