Book Holiday Homes in Jamestown

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Featured Holiday Homes in Jamestown

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

6 Bedroom home, heated 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.
Opens in a new window6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
Cumberland Lake House

Cumberland Lake House

Nancy
When you stay at this vacation home in Nancy, you'll be 7 minutes by car from Cumberland Point Recreation Area.
Opens in a new windowCumberland Lake House
Boating Mecca: Near Dale Hollow Lake & Golf!

Boating Mecca: Near Dale Hollow Lake & Golf!

Burkesville
The price is AU$266 per night from 21 Sept to 22 Sept
AU$266
21 Sept - 22 Sept
includes taxes & fees
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 ...
Opens in a new windowBoating Mecca: Near Dale Hollow Lake & Golf!
Save an average of 15% on thousands of hotels when you're signed in
3 miles from Wolf Creek Dam! Boat and camper parking available

3 miles from Wolf Creek Dam! Boat and camper parking available

Highway
Located in Albany, this vacation home is within a 15-minute drive of Wolf Creek National Fish Hatchery and Lake Cumberland State Resort Park.
Opens in a new window3 miles from Wolf Creek Dam! Boat and camper parking available
Charming 3BR house 2 mi to Dale Hollow Lake boat ramp and Sulphur Creek Resort

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

Burkesville
With a stay at this vacation home in Burkesville, you'll be within a 10-minute drive of Sulphur Creek Marina and Bear Creek Island.
Opens in a new windowCharming 3BR house 2 mi to Dale Hollow Lake boat ramp and Sulphur Creek Resort
4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

Monticello
Located in Monticello, this vacation home is on a lake, within a 15-minute drive of Cumberland River and Burnside Library.
Opens in a new window4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!
Lake house with boat ramp access across the street & tons of boat parking space.

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

Monticello
Located in Monticello, this vacation home is on a lake, within a 15-minute drive of Cumberland River and Mill Springs Mill Park.
Opens in a new windowLake house with boat ramp access across the street & tons of boat parking space.
3 bdrm/2 full bath home 1.5 miles from Wolf Creek Marina, Lake Cumberland

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

Nancy
With a stay at this vacation home in Nancy, you'll be a 1-minute walk from Wolf Creek Marina and 14 minutes by foot from Cumberland River.
Opens in a new window3 bdrm/2 full bath home 1.5 miles from Wolf Creek Marina, Lake Cumberland
Creekview Manor - Dale Hollow Lake with amazing views only minutes to docks

Creekview Manor - Dale Hollow Lake with amazing views only minutes to docks

Burkesville
When you stay at this vacation home in Burkesville, you'll be on a lake, within a 5-minute drive of Dale Hollow Reservoir and Hendrix Creek Marina.
Opens in a new windowCreekview Manor - Dale Hollow Lake with amazing views only minutes to docks
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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
204 Holiday Homes
Lowest Price
AU$212
Highest Price
AU$959
Popular accommodation
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍, Cumberland Lake House, Boating Mecca: Near Dale Hollow Lake & Golf!, 3 miles from Wolf Creek Dam! Boat and camper parking available, Charming 3BR house 2 mi to Dale Hollow Lake boat ramp and Sulphur Creek Resort, 4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!, Lake house with boat ramp access across the street & tons of boat parking space., 3 bdrm/2 full bath home 1.5 miles from Wolf Creek Marina, Lake Cumberland, Creekview Manor - Dale Hollow Lake with amazing views only minutes to docks

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
When you stay at Lake Cumberland State Resort Park in Jamestown, you'll be 6 minutes by car from Lowgap Island.
Opens in a new windowLake 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
The price is AU$959 per night from 5 Oct to 6 Oct
AU$959
5 Oct - 6 Oct
includes taxes & fees
When you stay at this vacation home in Jamestown, you'll be on the waterfront, within a 5-minute drive of The Park at Jamestown Square and Judicial Center Fountain ...
Opens in a new windowLAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Jamestown
The price is AU$592 per night from 21 Sept to 22 Sept
AU$592
21 Sept - 22 Sept
includes taxes & fees
Located in Jamestown, this cottage is a 1-minute drive from Cumberland River and 6 minutes from Jamestown Marina.
Opens in a new windowCozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Save an average of 15% on thousands of hotels when you're signed in
Timber Pointe Resort

Timber Pointe Resort

2 out of 5
2671 Kentucky 92, Jamestown, KY
The price is AU$212 per night from 1 Oct to 2 Oct
AU$212
1 Oct - 2 Oct
includes taxes & fees
When you stay at Timber Pointe Resort in Jamestown, you'll be in the entertainment district, within a 5-minute drive of Jamestown Marina and The Links Resort ...
Opens in a new windowTimber Pointe Resort
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.