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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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 ￥14,306
￥33,119 total
includes taxes & fees
Aug 26 - Aug 27
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 ￥16,308
￥55,548 total
includes taxes & fees
Aug 26 - Aug 27
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
Beach

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, (213 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 ￥23,195
￥64,329 total
includes taxes & fees
Sep 1 - Sep 2
Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay
Smart TV, fireplace

4. 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 ￥16,995
￥56,478 total
includes taxes & fees
Sep 3 - Sep 4
Hot Tub~Firepit~Riverfront~Near Lake Cumberland
Interior

5. 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 ￥17,882
￥42,669 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Lake Time Retreat
Terrace/patio

6. 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 ￥21,458
￥62,087 total
includes taxes & fees
Sep 3 - Sep 4
Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!
2 bedrooms, WiFi (free)

7. 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 ￥21,636
￥39,285 total
includes taxes & fees
Aug 26 - Aug 27
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Coffee/tea maker, fridge, microwave, oven

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 ￥25,750
￥62,556 total
includes taxes & fees
Aug 27 - Aug 28
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
Property grounds

9. 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 ￥14,077
￥52,742 total
includes taxes & fees
Aug 26 - Aug 27
Riverfront~Firepit~Fishing~20 Min Lake Cumberland~Game Table
Exterior

10. 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 ￥14,077
￥52,742 total
includes taxes & fees
Aug 26 - Aug 27
Cabin w/ Firepit~Pickleball~Arcade Games~River Boat Ramp~20 Min Lake Cumberland
Outdoor spa tub

11. 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 ￥15,278
￥54,237 total
includes taxes & fees
Aug 27 - Aug 28
HOT TUB~Dog Friendly Cabin~Fishing~River boat ramp~20 Min to Lake Cumberland
Exterior

12. 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, (8 reviews)
"The stay was very nice and peaceful "
United States
earl c.
The price is ￥15,278
￥54,237 total
includes taxes & fees
Aug 27 - Aug 28
Hot Tub & Firepit~Game Center~Lake Cumberland~Family Friendly~River Boat Ramp
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 ￥14,077
￥52,742 total
includes taxes & fees
Aug 27 - Aug 28
Riverfront View~Boat Ramp~Foosball~Family Friendly Cabin~20 Min Lake Cumberland
Exterior

14. 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 ￥15,278
￥54,237 total
includes taxes & fees
Aug 27 - Aug 28
Fishing~HotTub&Sauna~Pickleball~PingPong~Lake Cumberland~Playground~Firepit
Terrace/patio

15. 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 ￥28,611
￥56,073 total
includes taxes & fees
Aug 26 - Aug 27
New Rustic Home Near State Dock
Exterior

16. 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 ￥15,278
￥54,237 total
includes taxes & fees
Aug 27 - Aug 28
Cabin w/ River Boat Ramp~Private HotTub~Sauna~Lake Cumberland~Firepit~Pickleball
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 ￥15,292
￥54,285 total
includes taxes & fees
Aug 27 - Aug 28
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 ￥31,790
￥65,184 total
includes taxes & fees
Aug 26 - Aug 27
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
Property grounds

19. 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.
Charming A-frame with Lake Cumberland Views
Smart TV, fireplace

20. 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 ￥14,306
￥33,119 total
includes taxes & fees
Aug 26 - Aug 27
B - New near Jamestown Dock
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

Dale Hollow Lake State Resort Park

Dale Hollow Lake State Resort Park

8/10 Good
"Pros: Good place to stay. Good food in the restaurant. Nice views and great walking trails! A few cons: Our room had a faucet that dripped. No way to shut it off. Air unit was noisy. Restaurant daily offerings were a bit confusing."
Curt 3-night trip
Posted 10 hours ago
Dale Hollow Lake State Resort Park

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:

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Look no further and take a look at our great range of rental properties in Jamestown!

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: Visitors give good reviews to this Jamestown vacation home rental, which 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.

How many vacation rentals are there in Jamestown?

With 44 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.