Jamestown Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Jamestown Vacation Homes

Cumberland Lake House
Exterior

Cumberland Lake House

Cumberland Lake House
Charming 3BR house 2 mi to Dale Hollow Lake boat ramp and Sulphur Creek Resort
Fridge, microwave, oven, stovetop

Charming 3BR house 2 mi to Dale Hollow Lake boat ramp and Sulphur Creek Resort

10.0 out of 10, Exceptional, (4)
"Great stay in immaculate property. "
Charming 3BR house 2 mi to Dale Hollow Lake boat ramp and Sulphur Creek Resort
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community
Microwave, oven, stovetop, dishwasher

Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community

9.6 out of 10, Exceptional, (49)
"Easily accessible and the hosts are great communicators for everything. "
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
Outdoor dining

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

10.0 out of 10, Exceptional, (147)
"Great Experience on the property and on the Lake!! "
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland
Fridge, microwave, oven, stovetop

Charming 5-bedroom/3-bath home with easy access to Lake Cumberland

10.0 out of 10, Exceptional, (1)
"Jenn was super responsive and gave us plenty of info on fishing/boating access in the area. The house was a great size with a cute unique layout. Huge deck for plenty of outside hang time and close to a boat ramp to easily drop my canoe in. Just a few minutes from the State Park too! "
The price is CA $325
CA $671 total
includes taxes & fees
Aug 24 - Aug 25
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland
Lake House near Green River Lake and minutes from several marinas.
Outdoor dining

Lake House near Green River Lake and minutes from several marinas.

9.2 out of 10, Wonderful, (87)
"Great stay. "
Lake House near Green River Lake and minutes from several marinas.
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
Exterior

LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups

10.0 out of 10, Exceptional, (3)
"Everglow Hollow was great! We stayed for a long weekend and it was the perfect place to relax, while not being too far away from Lake Cumberland. Host also responded to questions right away and were very helpful. "
The price is CA $96
CA $250 total
includes taxes & fees
Aug 25 - Aug 26
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
Lake house with boat ramp access across the street & tons of boat parking space.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (78)
"Everything was so good, the place was amazing and the area was beautiful. We are ready to go again!! Thanks for sharing your place with us!,"
Lake house with boat ramp access across the street & tons of boat parking space.
"Eagle's Cliff" at Lake Cumberland. Relaxing Beautiful Front Porch Lake View!
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (14)
"Our absolute only complaint is no washer or dryer. The place is clean,nice,cozy, great location. We will stay again and recommend this place to others. "
"Eagle's Cliff" at Lake Cumberland. Relaxing Beautiful Front Porch Lake View!
3 bdrm/2 full bath home 1.5 miles from Wolf Creek Marina, Lake Cumberland
Exterior

3 bdrm/2 full bath home 1.5 miles from Wolf Creek Marina, Lake Cumberland

10.0 out of 10, Exceptional, (5)
"The house setup was very spacious and accomadating. We where overall impressed with this house."
3 bdrm/2 full bath home 1.5 miles from Wolf Creek Marina, Lake Cumberland
"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake
Exterior

"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake

8.4 out of 10, Very good, (20)
"Nice place.. pretty cabin"
"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake
King bed, hot tub & jacuzzi with no hidden fees!
Game room

King bed, hot tub & jacuzzi with no hidden fees!

9.6 out of 10, Exceptional, (47)
"Great location, beautiful view and secluded."
King bed, hot tub & jacuzzi with no hidden fees!
Historic Union Chapel Elementary School near Cumberland River & Lake
Fridge, microwave, oven, stovetop

Historic Union Chapel Elementary School near Cumberland River & Lake

10.0 out of 10, Exceptional, (36)
"Very nice accommodation not far from Jamestown the owner greeted me when i arrived and coffee and snacks were available I would recommend this great opportunity for anyone that is going to Jamestown "
The price is CA $139
CA $184 total
includes taxes & fees
Aug 24 - Aug 25
Historic Union Chapel Elementary School near Cumberland River & Lake
Cozy modern farmhouse w/ garage- Only 5 miles to Lake Cumberland!
Exterior

Cozy modern farmhouse w/ garage- Only 5 miles to Lake Cumberland!

9.8 out of 10, Exceptional, (12)
"Great stay"
Cozy modern farmhouse w/ garage- Only 5 miles to Lake Cumberland!
Charming 3-bedroom house with WiFi, AC just 2 miles from Dale Hallow lake
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC just 2 miles from Dale Hallow lake

10.0 out of 10, Exceptional, (1)
"Lovely little home; convenient to Albany, KY and Byrdstown, TN."
Charming 3-bedroom house with WiFi, AC just 2 miles from Dale Hallow lake
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
Fridge, microwave, oven, stovetop

Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

10.0 out of 10, Exceptional, (15)
"Our second stay at the same location was even better than the first stay. "
The price is CA $225
CA $546 total
includes taxes & fees
Sep 1 - Sep 2
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
Large family home w dinning by Lindsey Wilson
TV, offices

Large family home w dinning by Lindsey Wilson

9.6 out of 10, Exceptional, (4)
"Like being home. Great place to stay"
The price is CA $140
CA $236 total
includes taxes & fees
Aug 25 - Aug 26
Large family home w dinning by Lindsey Wilson
Sunshine Escape: Spacious 6-BDR Home w/ Patio, Fire Pit & 2 Miles to Marina
Property grounds

Sunshine Escape: Spacious 6-BDR Home w/ Patio, Fire Pit & 2 Miles to Marina

10.0 out of 10, Exceptional, (4)
"Very nice property, close to marina. All the information in the listing is accurate."
Sunshine Escape: Spacious 6-BDR Home w/ Patio, Fire Pit & 2 Miles to Marina
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!
Terrace/patio

Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!

9.8 out of 10, Exceptional, (8)
"Excellent bang for your buck! Truly a wonderful stay and great for the price! I will DEFINITELY be trying to come back again! Stay with confidence! "
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!
Little blue house on the lake
Interior

Little blue house on the lake

9.0 out of 10, Wonderful, (21)
"We enjoyed our stay and ended up buying a river home in kentucky. "
Little blue house on the lake
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jamestown Hotel Reviews

Timber Pointe Resort

Timber Pointe Resort

10/10 Excellent
"Very clean. Fun environment both for adults and kiddos :) family owned. We will be back for sure!"
Sherry 1-night trip
Posted 3 days ago
Timber Pointe Resort