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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

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
$186 nightly
The price is $205
Jul 31 - Aug 1
Total with taxes and fees
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.
$191 nightly
The price is $211
Jul 31 - Aug 1
Total with taxes and fees
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Coffee/tea maker, fridge, microwave, oven

3. 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.
$357 nightly
The price is $394
Jul 31 - Aug 1
Total with taxes and fees
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
Smart TV, fireplace

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, (18 reviews)
"Such a lovely property. Very cozy and inviting. We will definitely stay again."
United States
Jennifer S.
$331 nightly
The price is $364
Aug 25 - Aug 26
Total with taxes and fees
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
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.
$244 nightly
The price is $268
Aug 3 - Aug 4
Total with taxes and fees
Cozy Lake Time Retreat
Outdoor dining

6. "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.
$292 nightly
The price is $321
Aug 13 - Aug 14
Total with taxes and fees
"The Bee Hive" 1 mile from Lake Cumberland/Jamestown Marina
Smart TV, fireplace

7. 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.
$328 nightly
The price is $361
Aug 25 - Aug 26
Total with taxes and fees
Hot Tub~Firepit~Riverfront~Near Lake Cumberland
Terrace/patio

8. 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.
$372 nightly
The price is $410
Jul 31 - Aug 1
Total with taxes and fees
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
Terrace/patio

9. 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.
$385 nightly
The price is $424
Aug 25 - Aug 26
Total with taxes and fees
Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!
Terrace/patio

10. New Rustic Home Near State Dock

New Rustic Home Near State Dock
Jamestown
9.6 out of 10, Exceptional, (9 reviews)
"This property is absolutely amazing so clean and easy to get to! "
United States
Bailee J.
$320 nightly
The price is $353
Aug 2 - Aug 3
Total with taxes and fees
New Rustic Home Near State Dock
Smart TV, fireplace

11. B - New near Jamestown Dock

B - New near Jamestown Dock
Jamestown
9.6 out of 10, Exceptional, (24 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.
$186 nightly
The price is $205
Jul 31 - Aug 1
Total with taxes and fees
B - New near Jamestown Dock
Property grounds

12. 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.
$334 nightly
The price is $368
Aug 9 - Aug 10
Total with taxes and fees
Charming A-frame with Lake Cumberland Views
Interior

13. 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.
$429 nightly
The price is $473
Aug 2 - Aug 3
Total with taxes and fees
Great place to gather near Lake Cumberland
Exterior

14. 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.
$300 nightly
The price is $330
Aug 25 - Aug 26
Total with taxes and fees
Cabin w/ Firepit~Pickleball~Arcade Games~River Boat Ramp~20 Min Lake Cumberland
Property grounds

15. 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
$300 nightly
The price is $330
Aug 25 - Aug 26
Total with taxes and fees
Riverfront~Firepit~Fishing~20 Min Lake Cumberland~Game Table
Exterior

16. 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.
$300 nightly
The price is $330
Aug 25 - Aug 26
Total with taxes and fees
Riverfront View~Boat Ramp~Foosball~Family Friendly Cabin~20 Min Lake Cumberland
Outdoor dining

17. 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.
$468 nightly
The price is $516
Aug 3 - Aug 4
Total with taxes and fees
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
Exterior

18. 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.
$311 nightly
The price is $343
Aug 25 - Aug 26
Total with taxes and fees
Hot Tub & Firepit~Game Center~Lake Cumberland~Family Friendly~River Boat Ramp
Coffee/tea maker, fridge, microwave, oven

19. 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.
$230 nightly
The price is $254
Jul 31 - Aug 1
Total with taxes and fees
The Lodge Lake Retreat – Family-Friendly with Private River Access
Exterior

20. 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.
$312 nightly
The price is $344
Aug 25 - Aug 26
Total with taxes and fees
Fishing~HotTub&Sauna~Pickleball~PingPong~Lake Cumberland~Playground~Firepit
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

Days Inn by Wyndham Columbia Kentucky

Days Inn by Wyndham Columbia Kentucky

8/10 Good
"My room was clean but a bit run-down once I noticed details (patched wallpaper, cracked lampshades, etc.). Breakfast was standard."
Jeff 3-night trip
Posted 2 days ago
Days Inn by Wyndham Columbia Kentucky

Find out more about Jamestown

Everything you need to know about Jamestown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Jamestown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jamestown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Jamestown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jamestown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Jamestown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $160 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Jamestown rentals

At Expedia, we put the best Jamestown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Jamestown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jamestown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jamestown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 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.