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
$189 nightly
The price is $208
Aug 31 - Sep 1
Total with taxes and fees
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.
$318 nightly
The price is $349
Aug 31 - Sep 1
Total with taxes and fees
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, (214 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
$355 nightly
The price is $391
Sep 1 - Sep 2
Total with taxes and fees
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.
$323 nightly
The price is $355
Sep 1 - Sep 2
Total with taxes and fees
Hot Tub~Firepit~Riverfront~Near Lake Cumberland
2 bedrooms, WiFi (free)

5. 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.
$159 nightly
The price is $176
Aug 31 - Sep 1
Total with taxes and fees
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Interior

6. 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 31 - Sep 1
Total with taxes and fees
Cozy Lake Time Retreat
Terrace/patio

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.
$355 nightly
The price is $391
Sep 1 - Sep 2
Total with taxes and fees
Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!
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.
$290 nightly
The price is $319
Aug 31 - Sep 1
Total with taxes and fees
Cabin w/ Firepit~Pickleball~Arcade Games~River Boat Ramp~20 Min Lake Cumberland
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
$302 nightly
The price is $332
Aug 31 - Sep 1
Total with taxes and fees
Riverfront~Firepit~Fishing~20 Min Lake Cumberland~Game Table
Coffee/tea maker, fridge, microwave, oven

10. 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.
$357 nightly
The price is $394
Sep 2 - Sep 3
Total with taxes and fees
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
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.
$310 nightly
The price is $341
Sep 1 - Sep 2
Total with taxes and fees
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.
$310 nightly
The price is $341
Sep 1 - Sep 2
Total with taxes and fees
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.
$302 nightly
The price is $332
Sep 1 - Sep 2
Total with taxes and fees
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.
$310 nightly
The price is $341
Sep 1 - Sep 2
Total with taxes and fees
Fishing~HotTub&Sauna~Pickleball~PingPong~Lake Cumberland~Playground~Firepit
Exterior

15. 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.
$310 nightly
The price is $341
Sep 1 - Sep 2
Total with taxes and fees
Cabin w/ River Boat Ramp~Private HotTub~Sauna~Lake Cumberland~Firepit~Pickleball
Exterior

16. 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.
$310 nightly
The price is $341
Sep 1 - Sep 2
Total with taxes and fees
Hot Tub~River Boat Ramp~Pickleball~Lake Cumberland~Family Friendly Cabin
Terrace/patio

17. 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.
$320 nightly
The price is $353
Aug 31 - Sep 1
Total with taxes and fees
New Rustic Home Near State Dock
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.
$372 nightly
The price is $410
Aug 31 - Sep 1
Total with taxes and fees
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
Smart TV, fireplace

19. 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.
$189 nightly
The price is $208
Aug 31 - Sep 1
Total with taxes and fees
B - New near Jamestown Dock
Outdoor dining

20. 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.
$456 nightly
The price is $503
Sep 1 - Sep 2
Total with taxes and fees
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
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

Timber Pointe Resort

Timber Pointe Resort

10/10 Excellent
"We would stay there again"
Barry 1-night trip
Posted 2 days ago
Timber Pointe Resort

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 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.