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
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Jamestown vacation rentals

2 bedrooms, free WiFi

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, (10 reviews)
"Nice location- property manager was bery nice and responsive"
United States
Stephen
The price is AED 455
AED 794 total
includes taxes & fees
25 Jun - 26 Jun
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Dining

New Near Jamestown Dock - A

New Near Jamestown Dock - A
Jamestown
9.8 out of 10, Exceptional, (24 reviews)
"Great stay"
United States
Rob W.
The price is AED 331
AED 753 total
includes taxes & fees
22 Jun - 23 Jun
New Near Jamestown Dock - A
Smart TV, fireplace

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, (15 reviews)
"Such a lovely property. Very cozy and inviting. We will definitely stay again."
United States
Jennifer S.
The price is AED 409
AED 1,322 total
includes taxes & fees
29 Jun - 30 Jun
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
Exterior

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 440
AED 1,361 total
includes taxes & fees
13 Jul - 14 Jul
Cabin w/ Firepit~Pickleball~Arcade Games~River Boat Ramp~20 Min Lake Cumberland
Smart TV, fireplace

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
28 Jun - 29 Jun
Hot Tub~Firepit~Riverfront~Near Lake Cumberland
Exterior

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, (5 reviews)
"The stay was very nice and peaceful "
United States
earl c.
The price is AED 365
AED 1,266 total
includes taxes & fees
28 Jun - 29 Jun
Hot Tub & Firepit~Game Center~Lake Cumberland~Family Friendly~River Boat Ramp
Outdoor spa tub

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 AED 369
AED 1,275 total
includes taxes & fees
29 Jun - 30 Jun
HOT TUB~Dog Friendly Cabin~Fishing~River boat ramp~20 Min to Lake Cumberland
Exterior

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 AED 377
AED 1,284 total
includes taxes & fees
29 Jun - 30 Jun
Fishing~HotTub&Sauna~Pickleball~PingPong~Lake Cumberland~Playground~Firepit
Exterior

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 AED 325
AED 1,219 total
includes taxes & fees
30 Jun - 1 Jul
Riverfront View~Boat Ramp~Foosball~Family Friendly Cabin~20 Min Lake Cumberland
Exterior

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

Hot Tub~River Boat Ramp~Pickleball~Lake Cumberland~Family Friendly Cabin
Jamestown
9.0 out of 10, Wonderful, (2 reviews)
The price is AED 353
AED 1,253 total
includes taxes & fees
29 Jun - 30 Jun
Hot Tub~River Boat Ramp~Pickleball~Lake Cumberland~Family Friendly Cabin
Exterior

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 AED 456
AED 1,383 total
includes taxes & fees
29 Jun - 30 Jun
Cabin w/ River Boat Ramp~Private HotTub~Sauna~Lake Cumberland~Firepit~Pickleball
Property grounds

Riverfront~Firepit~Fishing~20 Min Lake Cumberland~Game Table

Riverfront~Firepit~Fishing~20 Min Lake Cumberland~Game Table
Jamestown
The price is AED 504
AED 1,443 total
includes taxes & fees
22 Jul - 23 Jul
Riverfront~Firepit~Fishing~20 Min Lake Cumberland~Game Table
Beach

Unique Hexagon Cottage-Atop JTown Marina-Boat Parking-3 En Suite Baths-Pets okay

Unique Hexagon Cottage-Atop JTown Marina-Boat Parking-3 En Suite Baths-Pets okay
Jamestown
10.0 out of 10, Exceptional, (204 reviews)
"House was great, clean, modern and well stocked"
United States
Scott B.
The price is AED 522
AED 1,422 total
includes taxes & fees
28 Jun - 29 Jun
Unique Hexagon Cottage-Atop JTown Marina-Boat Parking-3 En Suite Baths-Pets okay
Fridge, microwave, oven, stovetop

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, (2 reviews)
"Th place was extremely clean, check in was simple and easy, the listing was exactly as described. The sheets on the bed were amazing and the beds were comfortable "
United States
Dillon R.
The price is AED 455
AED 968 total
includes taxes & fees
22 Jul - 23 Jul
The Lodge Lake Retreat – Family-Friendly with Private River Access
Interior

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 982 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Lake Time Retreat
Sport court

Lake Cumberland Condo Near State Park - Gated Community - Family Friendly

Lake Cumberland Condo Near State Park - Gated Community - Family Friendly
Jamestown
10.0 out of 10, Exceptional, (1 review)
"Great location! Kids love the pool"
United States
Jaime H.
The price is AED 661
AED 1,413 total
includes taxes & fees
28 Jun - 29 Jun
Lake Cumberland Condo Near State Park - Gated Community - Family Friendly
Fridge, microwave, oven, stovetop

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, (7 reviews)
"This house was beautiful and perfect for what we needed. "
United States
Shavona M.
4BR Lake Cumberland Cabin - Hot Tub, Fire Pit, Near Boat Ramps, Pet Friendly
Terrace/patio

New Rustic Home Near State Dock

New Rustic Home Near State Dock
Jamestown
10.0 out of 10, Exceptional, (8 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
27 Jun - 28 Jun
New Rustic Home Near State Dock
Property grounds

Charming A-frame with Lake Cumberland Views

Charming A-frame with Lake Cumberland Views
Jamestown
4.0 out of 10, (1 review)
"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 496
AED 1,320 total
includes taxes & fees
22 Jun - 23 Jun
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

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
"The house was very clean and had everything we needed. View of the lake is amazing! Beds were comfortable and plenty of room for all 12 of us. Kids loved the basement area!"
Amy H. 4-night trip
Posted 3 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: 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.