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
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, a water park, and a garden. Popular attractions Firebrook Community Park and ...
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
Stay at this vacation home in Burkesville. Enjoy free WiFi, a garden, and patios. Popular attractions Sulphur Creek Marina and Dale Hollow Lake State Resort ...
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 NZ$856 per night from 8 Apr to 9 Apr
NZ$856
includes taxes & fees
8 Apr - 9 Apr
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Wolf Creek Marina ...
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
Stay at this vacation home in Nancy. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Mill Springs Battlefield and Mill Springs Mill ...
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
Stay at this vacation home in Byrdstown. Enjoy free WiFi, private pools, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
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
Stay at this vacation home in Burkesville. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Dale Hollow Reservoir and Dale Hollow ...
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
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, private pools, and a garden. Popular attractions Firebrook Community Park and ...
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
Book a stay at this family-friendly vacation home in Monticello. Enjoy patios, cable/satellite TV service, and in-room washers/dryers. Popular attractions Big ...
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
Stay at this vacation home in Monticello. Enjoy free WiFi, a garden, and patios. Popular attractions Conley Bottom Marina and Lake Cumberland Winery are located ...
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
NZ$183
Highest Price
NZ$856
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 NZ$183 per night from 2 Apr to 3 Apr
NZ$183
includes taxes & fees
2 Apr - 3 Apr
Stay at this 3-star family-friendly holiday park in Jamestown. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. ...
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
Book a stay at this family-friendly vacation home in Jamestown. Enjoy free WiFi, a water park, and a garden. Our guests praise the helpful staff in our reviews. ...
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
Book a stay at this family-friendly cottage in Jamestown. Enjoy free WiFi, a water park, and a garden. Our guests praise the helpful staff in our reviews. Popular ...
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
Stay at this cottage in Jamestown. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Jamestown Marina and Lake Cumberland State ...
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Don't see what you're looking for?
See all available properties in Jamestown
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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.