Jamestown Rentals

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21 Houses

(2) Excellent 

19

Pleasant Valley

Kentucky / Jamestown

Jamestown house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$172

Price per night from

$172

17

Lake Cumberland Vacation Rental

Kentucky / Jamestown

Jamestown house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$115

Price per night from

$115

21

Lake Cumberland Lakefront home: 4BDR, 4BA; close to marina!

Kentucky / Jamestown

Jamestown house

4 14 2 nights min

  • 4 bedrooms
  • sleeps 14
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$344

Price per night from

$344

25

NEW! Rustic Home on 1 Acre Near Lake Cumberland!

Kentucky / Jamestown

Jamestown house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$126

Responds fast!
avg. 28 minutes

Price per night from

$126

Great rentals within 20 miles that match your search

Distance approx 19.5 km from Jamestown

9

The Chalet

Kentucky / Nancy

Nancy log cabin

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$163

Price per night from

$163

Distance approx 9.99 km from Jamestown

17

The LAKE HOUSE at Beaver Creek

Kentucky / Monticello

Monticello house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$114

Price per night from

$114

Distance approx 17.54 km from Jamestown

18

The Best Lake House On Lake Cumberland

Kentucky / Nancy

Nancy house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$458

Price per night from

$458

Distance approx 8.64 km from Jamestown

(1) Excellent 

51

"Look Out Lodge on Lake Cumberland"

Kentucky / Russell Springs

Russell Springs log cabin

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly

Price per night from

$573

Responds fast!
avg. 2 hours 37 minutes

Price per night from

$573

Distance approx 19.5 km from Jamestown

9

The Homestead

Kentucky / Nancy

Nancy log cabin

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$163

Price per night from

$163

Distance approx 19.53 km from Jamestown

(1) Excellent 

9

The Oaks

Kentucky / Nancy

Nancy log cabin

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$174

Price per night from

$174

Distance approx 15.71 km from Jamestown

(1) Excellent 

19

Garrison Farmstead - Grandma's Cottage

Kentucky / Columbia

Columbia house

4 10 1 night min

  • 4 bedrooms
  • sleeps 10
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$344

Responds fast!
avg. 58 minutes

Price per night from

$344

Distance approx 4.28 km from Jamestown

(3) Excellent 

18

3 bdr house overlooking Lake Cumberland tributary

Kentucky / Russell Springs

Russell Springs house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$138

Price per night from

$138

Distance approx 15.71 km from Jamestown

(1) Very Good 

18

Garrison Farmstead - The Lake House/CABIN

Kentucky / Columbia

Columbia house

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$229

Responds fast!
avg. 58 minutes

Price per night from

$229

Distance approx 11.74 km from Jamestown

(2) Excellent 

18

Eagles Bluff Getaway!

Kentucky / Monticello

Monticello house

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$206

Responds fast!
avg. 52 minutes

Price per night from

$206

Distance approx 11.67 km from Jamestown

(8) Excellent 

Certificate of Excellence

40

Blue Cabin in Quiet Lake Community

Kentucky / Monticello

Monticello house

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Certificate of Excellence

Price per night from

$86

Responds fast!
avg. 5 minutes

Price per night from

$86

Distance approx 12.2 km from Jamestown

(6) Excellent 

30

Hickory Ridge Guest House

Kentucky / Albany

Albany house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning
“You'll love this place!” A clean, well lighted, place, with lots of room for the family and friends. If you are looking for a place just a couple of minutes to Lake Cumberland at Grider Hill Marina, this is it. Enjoy the water during the day, and enj
…see more

Price per night from

$184

Price per night from

$184

Distance approx 14.34 km from Jamestown

(1) Very Good 

4

Scenic, Lakeview House, Located in Beautiful Woods

Kentucky / Monticello

Monticello house

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$144

Price per night from

$144

Distance approx 5.18 km from Jamestown

27

Serene & Quiet Russell Springs Log Cabin!

Kentucky / Russell Springs

Russell Springs log cabin

3 4 min stay varies

  • 3 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$144

Responds fast!
avg. 28 minutes

Price per night from

$144

Distance approx 15.71 km from Jamestown

26

Garrison Farmstead - The Little Farmhouse

Kentucky / Columbia

Columbia house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$264

Responds fast!
avg. 58 minutes

Price per night from

$264

Distance approx 10.09 km from Jamestown

24

Cozy Monticello Cabin with Lake Views!

Kentucky / Alpha

Alpha cottage

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$98

Responds fast!
avg. 28 minutes

Price per night from

$98

Distance approx 9.98 km from Jamestown

29

NEW! Lake Cumberland Home w/Deck,Grill & Fire Pit!

Kentucky / Alpha

Alpha house

5 16 min stay varies

  • 5 bedrooms
  • sleeps 16
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$287

Responds fast!
avg. 15 minutes

Price per night from

$287