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Compare 199 Vacation Homes in Jamestown with updated reviews, rates, and availability.

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY

10.0 out of 10, Exceptional, (136)
"Was everything we were looking for. The view was amazing. The local was close to stores and restaurants. The home had everything we needed. "
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY

Lake Cumberland Hideaway #1-2 miles from Jtown Marina! Boat Parking & Fire Pit!

10.0 out of 10, Exceptional, (155)
"We had a great time here, was clean, and convenient!"
Lake Cumberland Hideaway #1-2 miles from Jtown Marina! Boat Parking & Fire Pit!

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

9.8 out of 10, Exceptional, (32)
"Great place to hang out with family."
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

Cumberland Get-A-Way located at entrance of State Park

10.0 out of 10, Exceptional, (16)
"We had a really nice time at Brandon’s place! Everything we needed. He was wonderful to work with too. It’s perfect for a large family and so close to State park and the dam, for getting in the water."
Cumberland Get-A-Way located at entrance of State Park

Lake house with boat ramp access across the street & tons of boat parking space.

9.8 out of 10, Exceptional, (70)
"Our third year at this location for our family and friends get together. Great location. Perfect for our event! Thanks to the host for all the preparations. Highly satisfied and will very likely use the same property again next year. "
Lake house with boat ramp access across the street & tons of boat parking space.

Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip

9.8 out of 10, Exceptional, (72)
"Very clean and nice property very close to Dale Hollow golf course. Host was very accommodating. Will stay here again if possible. "
Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip

Little blue house on the lake

9.6 out of 10, Exceptional, (15)
"The property was very clean well organized in a home away from home."
Little blue house on the lake

Gorgeous new 3 bdr house right by entrance to Dale Hollow Lake State Resort Park

10.0 out of 10, Exceptional, (3)
"The location and house were excellent for our needs. We would definitely book this rental again"
Gorgeous new 3 bdr house right by entrance to Dale Hollow Lake State Resort Park

"Eagle's Cliff" at Lake Cumberland. Relaxing Beautiful Front Porch Lake View!

9.4 out of 10, Exceptional, (9)
"What we enjoyed the most was sitting on the deck and taking in the view of Lake Cumberland. It's a quiet and cozy place on a lightly-traveled road way out in the country."
"Eagle's Cliff" at Lake Cumberland. Relaxing Beautiful Front Porch Lake View!

Homey cottage near the Banks of the Cumberland & Dale Hollow Lake!

10.0 out of 10, Exceptional, (11)
"The communion with the owner was easy and quick! Had a great stay."
The price is SAR 431
SAR 732 total
includes taxes & fees
29 May - 30 May
Homey cottage near the Banks of the Cumberland & Dale Hollow Lake!

Cocktail Cove 4 bedroom 2 bath by Jamestown Marina

10.0 out of 10, Exceptional, (25)
"We had a wonderful time and it was so nice to be so close to the marina!"
Cocktail Cove 4 bedroom 2 bath by Jamestown Marina

3 Bdrm Lake House Getaway - Three Minutes To Launch!

10.0 out of 10, Exceptional, (101)
"Such a nice place for a trip to the lake. Everything was comfortable and relaxing. We had all we needed, beds were comfy, plenty of space for everyone, things were clean and easy to use. We would definitely stay again!"
3 Bdrm Lake House Getaway - Three Minutes To Launch!

Historic Union Chapel School-Two Room, near Cumberland River & Lake Cumberland

10.0 out of 10, Exceptional, (45)
"We come every year for the longest yard sale! Quiet, cool & restful place! Look forward to this stop every year!"
The price is SAR 469
SAR 600 total
includes taxes & fees
3 Jun - 4 Jun
Historic Union Chapel School-Two Room, near Cumberland River & Lake Cumberland

Brand new custom lake house with breathtaking panoramic views

4.0 out of 10, (1)
"The house was nice and new as the photos show. It was a little too secluded from civilization with no WiFi. It also had no direct lake access. There house didn’t look like it had been cleaned. Our feet were black from the floors by the end of the first night. The dishes were dirty, the towels were dirty, and the bedspread in the bunk room had white residue on it that looked like c*m. Random bugs everywhere upon arrival. I tried to complain to the owner and asked for the cleaning fee back because...
Brand new custom lake house with breathtaking panoramic views

Pet friendly suite that overlooks Lake Cumberland's Safe Harbor Jamestown #107

2.0 star property
8.0 out of 10, Very Good, (2)
"This was a very quiet relaxing spot. The view from the hotel room is gorgeous. The patio overlooking Lake Cumberland was so relaxing. Rent a boat or bring one it is a boaters dream come true. The office staff was great very friendly. House keeping was great. I would highly recommend this location. The areas around was great. All the parks and nature areas. The views are breath taking. We were only three hours away from home. A vacation we truly needed . "
Pet friendly suite that overlooks Lake Cumberland's Safe Harbor Jamestown #107

Prather Place, Spacious, Deck And View, Entertaining Basement, Minutes to Marina

10.0 out of 10, Exceptional, (140)
"Plenty of room for all of us and the kitchen is outstanding! We enjoyed our stay enormously’ Loved the sunrises!"
Prather Place, Spacious, Deck And View, Entertaining Basement, Minutes to Marina

Million Dollar View! Large Lakehouse Over-Looking Lee's Ford Marina

9.8 out of 10, Exceptional, (89)
"The house was clean, had great games to play with the family, and was welcoming. It was very spacious and comfortably housed seven people. I would definitely rent again. "
The price is SAR 1,313
SAR 2,671 total
includes taxes & fees
2 Jun - 3 Jun
Million Dollar View! Large Lakehouse Over-Looking Lee's Ford Marina

Boating Mecca: Near Dale Hollow Lake & Golf!

10.0 out of 10, Exceptional, (74)
"Couldn't have ask for a nicer place or better host. Everything was great except for the weather! I'm sure it will be better next time. Thanks"
The price is SAR 270
SAR 625 total
includes taxes & fees
10 Jun - 11 Jun
Boating Mecca: Near Dale Hollow Lake & Golf!

Beautiful Vacation Home on Lake Cumberland, Monticello, KY

10.0 out of 10, Exceptional, (121)
"An enjoyable place to stay."
Beautiful Vacation Home on Lake Cumberland, Monticello, KY

Lake house. Less than 3 miles from beautiful Lake Cumberland.

9.4 out of 10, Exceptional, (19)
"I was wonderful "
Lake house. Less than 3 miles from beautiful Lake Cumberland.
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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