Book Holiday Homes in Jamestown

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Featured Holiday Homes in Jamestown

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

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

Monticello
Located in Monticello, this vacation home is on the waterfront, within a 15-minute drive of Burnside Library and Cole Community Park.
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!
Boating Mecca: Near Dale Hollow Lake & Golf!

Boating Mecca: Near Dale Hollow Lake & Golf!

Burkesville
The price is AU$282 per night from 1 Apr to 2 Apr
AU$282
includes taxes & fees
1 Apr - 2 Apr
Located in Burkesville, this vacation home is on a lake, within a 10-minute drive of Dale Hollow Lake State Park and Dale Hollow Lake State Resort Park Golf ...
Boating Mecca: Near Dale Hollow Lake & Golf!
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

Monticello
The price is AU$770 per night from 30 Apr to 1 May
AU$770
includes taxes & fees
30 Apr - 1 May
When you stay at this vacation home in Monticello, you'll be on a lake and within a 5-minute drive of Cumberland River.
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
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Little blue house on the lake

Little blue house on the lake

Nancy
When you stay at this vacation home in Nancy, you'll be on a lake and 9 minutes by foot from Cumberland River.
Little blue house on the lake
Pool / Grill,  Dale Hollow Lake and nearby Sunset Marina with Mountain view

Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view

Byrdstown
With a stay at this vacation home in Byrdstown, you'll be on a lake, within a 5-minute drive of Dale Hollow Reservoir and Cordell Hull.
Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view
Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip

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

Burkesville
Located in Burkesville, this vacation home is on a lake, within a 15-minute walk of Dale Hollow Lake State Park and Dale Hollow Lake State Resort Park Golf ...
Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍

6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍

Monticello
Located in Monticello, this vacation home is within a 15-minute drive of Cumberland River and Burnside Library.
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Lake Cumberland Home 1/2 Mi to Beaver Creek Marina

Lake Cumberland Home 1/2 Mi to Beaver Creek Marina

Monticello
When you stay at this vacation home in Monticello, you'll be 14 minutes by car from Cumberland River.
Lake Cumberland Home 1/2 Mi to Beaver Creek Marina
1-Mile from Conley Bottom's ramp

1-Mile from Conley Bottom's ramp

Monticello
Located in Monticello, this vacation home is on a lake, within a 5-minute drive of Cumberland River and Conley Bottom Marina.
1-Mile from Conley Bottom's ramp
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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.

Jamestown Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Jamestown vacation homes are the perfect way for you to wing it.

Holiday houses in Jamestown let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Jamestown in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Jamestown adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Jamestown with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Jamestown vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Jamestown Holiday Homes essential information

Accommodation
198 Holiday Homes
Lowest Price
AU$167
Highest Price
AU$770
Popular accommodation
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!, Boating Mecca: Near Dale Hollow Lake & Golf!, Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!, Little blue house on the lake, Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view, Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip, 6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍 , Lake Cumberland Home 1/2 Mi to Beaver Creek Marina, 1-Mile from Conley Bottom's ramp

Top trending hotels in Jamestown

Lake Cumberland State Resort Park

Lake Cumberland State Resort Park

3 out of 5
5465 State Park Rd, Jamestown, KY
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 2 Apr to 3 Apr
AU$167
includes taxes & fees
2 Apr - 3 Apr
When you stay at Lake Cumberland State Resort Park in Jamestown, you'll be 6 minutes by car from Lowgap Island.
Lake Cumberland State Resort Park
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY

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

Jamestown
When you stay at this vacation home in Jamestown, you'll be on a lake, within a 5-minute drive of The Park at Jamestown Square and Judicial Center Fountain ...
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY
JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.

JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.

Jamestown
Located in Jamestown, this cottage is on a lake, a 1-minute drive from Cumberland River and 6 minutes from Jamestown Marina.
JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.
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NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

Jamestown
Located in Jamestown, this cottage is on a lake, a 1-minute drive from Cumberland River and 6 minutes from Jamestown Marina.
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
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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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^Subject to availability and chosen travel dates.