Vacation Rentals in Jamestown, KY: Compare 10+ Sites & Save

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  5.  Jamestown

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99 Best Vacation Rentals in Jamestown (Starting from $113)

Lake Cumberland Cabin - Spa, Firepit, Scenic Views
Lake Cumberland Cabin - Spa, Firepit, Scenic Views
House
Jamestown, KY, USA
4.5k from Jamestown center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Hot tubs

4 Bedrooms10 Guests
New to Booking
$283
Average price / night
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Clifty Creek Inn—Unit B
Clifty Creek Inn—Unit B
Cottage
Jamestown, KY, 42629, United States
2.7k from Jamestown center

AC, Barbecue, Free Parking, Heater, Internet, Microwave, No Smoking, TV

1 Bedroom6 Guests
9.6

Exceptional

14 reviews

$113
Average price / night
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Kentucky Coal Cabin 2 min from Lake Cumberland
Kentucky Coal Cabin 2 min from Lake Cumberland
House
Jamestown, KY, USA
4.8k from Jamestown center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family

2 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$294
Average price / night
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Clifty Creek Inn—Unit A
Clifty Creek Inn—Unit A
Cottage
Jamestown, KY, 42629, United States
3.1k from Jamestown center

AC, Internet, No Smoking, Outdoor Grill

1 Bedroom5 Guests
8.0

Good

2 reviews

$142
Average price / night
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Luxe Lake Cumberland Retreat with Decks on 1 Acre!
Luxe Lake Cumberland Retreat with Decks on 1 Acre!
House
Jamestown, KY, USA
5.8k from Jamestown center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

4 Bedrooms20 Guests
New to Booking
$798
Average price / night
Check Availability
3-bedroom house in charming Jamestown with easy access to boat ramp!
3-bedroom house in charming Jamestown with easy access to boat ramp!
House
Jamestown, KY, 42629, United States
4.3k from Jamestown center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Laundry, Microwave, No Smoking

3 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$214
Average price / night
Check Availability
Lake Cumberland Retreat with Deck and Views!
Lake Cumberland Retreat with Deck and Views!
House
Jamestown, KY, USA
6.1k from Jamestown center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

6 Bedrooms15 Guests
New to Booking
$763
Average price / night
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Lake Cumberland Jamestown New Home near State Park & Boat Ramps
Lake Cumberland Jamestown New Home near State Park & Boat Ramps
Cabin
Jamestown, KY, 42629, United States
4.3k from Jamestown center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

29 reviews

$280
Average price / night
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2 Mi to Lake Cumberland Family-Friendly Retreat!
2 Mi to Lake Cumberland Family-Friendly Retreat!
House
Jamestown, KY, USA
7.7k from Jamestown center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms10 Guests
New to Booking
$270
Average price / night
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Charming 5-bedroom/3-bath home with easy access to Lake Cumberland
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland
House
Jamestown, KY, 42629, United States
4.4k from Jamestown center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms18 Guests
9.6

Exceptional

5 reviews

$341
Average price / night
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2 Mi to Lake Cumberland Access Home with Grill
2 Mi to Lake Cumberland Access Home with Grill
House
Jamestown, KY, USA
8.5k from Jamestown center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms11 Guests
New to Booking
$411
Average price / night
Check Availability
Cumberland Get-A-Way located at entrance of State Park
Cumberland Get-A-Way located at entrance of State Park
House
Jamestown, KY, 42629, United States
4.9k from Jamestown center

AC, Arcade, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

7 Bedrooms28 Guests
10.0

Exceptional

19 reviews

$587
Average price / night
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Stylish cabin 4mins away from Cumberland Lake!
Stylish cabin 4mins away from Cumberland Lake!
Cabin
Jamestown, KY, 42629, United States
5.1k from Jamestown center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
9.6

Exceptional

13 reviews

$185
Average price / night
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Spacious 6-bedroom house with WiFi & AC in charming Jamestown lake ramp access
Spacious 6-bedroom house with WiFi & AC in charming Jamestown lake ramp access
House
Jamestown, KY, 42629, United States
5.2k from Jamestown center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$321
Average price / night
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Located on the picturesque shores of Lake Cumberland. \n
Located on the picturesque shores of Lake Cumberland. \n
House
Jamestown, KY, 42629, United States
5.3k from Jamestown center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

6 Bedrooms16 Guests
9.4

Superb

6 reviews

$339
Average price / night
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Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community
House
Jamestown, KY, 42629, United States
5.5k from Jamestown center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms10 Guests
9.4

Superb

55 reviews

$126
Average price / night
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Brand new serene log cabin on the banks of the Cumberland River in Jamestown.
Brand new serene log cabin on the banks of the Cumberland River in Jamestown.
Cabin
Jamestown, KY, 42629, United States
5.6k from Jamestown center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$416
Average price / night
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Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
House
Jamestown, KY, 42629, United States
5.8k from Jamestown center

AC, Arcade, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater

4 Bedrooms20 Guests
9.8

Exceptional

38 reviews

$482
Average price / night
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LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
House
Jamestown, KY, 42629, United States
6.1k from Jamestown center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen

5 Bedrooms16 Guests
10.0

Exceptional

165 reviews

$643
Average price / night
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Lake Cumberland Retreat w/ Deck & Views!
Lake Cumberland Retreat w/ Deck & Views!
House
Jamestown, KY, 42629, United States
6.1k from Jamestown center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Kitchen

6 Bedrooms15 Guests
9.2

Superb

12 reviews

$599
Average price / night
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The Bourbon House
The Bourbon House
House
Jamestown, KY, 42629, United States
6.2k from Jamestown center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

9 reviews

$163
Average price / night
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Spacious 3 bedroom apartment 3 miles from Wolf Creek Dam. Pet friendly!
Spacious 3 bedroom apartment 3 miles from Wolf Creek Dam. Pet friendly!
Apartment
Jamestown, KY, 42629, United States
6.2k from Jamestown center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, TV

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$158
Average price / night
Check Availability
Luxury Retreat Near Lake Cumberland and Minutes to Marina, Dam & Boat Launch
Luxury Retreat Near Lake Cumberland and Minutes to Marina, Dam & Boat Launch
House
Jamestown, KY, 42629, United States
6.5k from Jamestown center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

6 reviews

$246
Average price / night
Check Availability
DRIFT INN just 10 minutes from Jamestown Marina
DRIFT INN just 10 minutes from Jamestown Marina
House
Jamestown, KY, 42629, United States
6.5k from Jamestown center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms12 Guests
10.0

Exceptional

13 reviews

$447
Average price / night
Check Availability
Cozy 3 Bed Log Cabin at Jamestown Marina, Tucked Away in a Wooded Area #301
Cozy 3 Bed Log Cabin at Jamestown Marina, Tucked Away in a Wooded Area #301
Cabin
Jamestown, KY, 42629, United States
6.7k from Jamestown center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, Patio

3 Bedrooms8 Guests
7.8

Good

6 reviews

$199
Average price / night
Check Availability
3 Bed Log Cabin Located 0.5 miles from Safe Harbor Jamestown #302
3 Bed Log Cabin Located 0.5 miles from Safe Harbor Jamestown #302
Cabin
Jamestown, KY, 42629, United States
6.7k from Jamestown center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
7.8

Good

9 reviews

$212
Average price / night
Check Availability
Restful Rustic Farmhouse on Lake Cumberland
Restful Rustic Farmhouse on Lake Cumberland
Cottage
Jamestown, KY, 42629, United States
6.8k from Jamestown center

AC, Arcade, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms14 Guests
9.6

Exceptional

11 reviews

$573
Average price / night
Check Availability

Other accommodation types in Jamestown:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Jamestown.

Jamestown Vacation Rentals on the Map

Frequently Asked Questions

You can explore 99 verified vacation rentals in Jamestown. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Jamestown vary depending on the season, property size, and location. Rates typically start from around $113 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Jamestown include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Jamestown welcome pets. Currently, 30 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Jamestown often include amenities such as Fireplace/Heating, Kitchen, and Bedding/Linens. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.