Jamestown holiday lettings

We found 171 holiday rentals — enter your dates for availability

Discover a selection of 37 homes, 39 cabins and other holiday rentals in Jamestown that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, such as Wi-Fi and cable TV. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Jamestown

Showing deals for:6 Feb - 13 Feb

Image gallery for Dream cabin with mancave and views of Lake Cumberland.

Mancave
9.8 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)

Dream cabin with mancave and views of Lake Cumberland.

Nancy, KY

8% off
Price is £2,240
for 7 nights, 1 cabin
£320 per night
includes taxes & fees
Dream cabin with mancave and views of Lake Cumberland.

Find spaces that suit your style

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    Enjoy full kitchens, pools, gardens and more

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Delight in the lakeside landscape of Jamestown

The lake and parks provide a pleasant backdrop to your holiday home in Jamestown. This welcoming city is known for its restaurants, fishing and hiking. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Jamestown

Do you want to find things to do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Jamestown a fun place to get away to. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Lake Cumberland Winery (12.4 mi / 19.9 km)
  • Dale Hollow Lake State Resort Park Golf Course (25.8 mi / 41.6 km)
  • The Links Resort Golf Course (1.3 mi / 2.1 km)
  • Up the Creek Winery (22.6 mi / 36.4 km)

Exploring the natural features in Jamestown

Whether you're looking for fun outdoor activities or just want to take in the scenery, Jamestown is a great spot to appreciate mother nature. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Lake Cumberland State Resort Park (4 mi / 6.4 km)
  • Wolf Creek National Fish Hatchery (9 mi / 14.5 km)
  • Green River Lake (21.8 mi / 35.2 km)
  • Dale Hollow Reservoir (29.9 mi / 48.2 km)
  • Wolf Creek Recreation Area (7.3 mi / 11.7 km)
  • Mountain View Park (19 mi / 30.6 km)

Frequently asked questions

What is the best area to stay in Jamestown when booking a holiday rental?
When considering a holiday rental in Jamestown, Kentucky, the area around Lake Cumberland is one of the best options. This picturesque locale is not only known for its stunning natural beauty but also offers a wealth of recreational activities. Visitors will find a variety of properties available, ranging from charming cabins to modern lakeside homes, making it an ideal spot for families or groups of friends seeking a relaxing getaway.

Staying near Lake Cumberland provides easy access to the lake's numerous attractions, including fishing, boating, and hiking in the surrounding state parks. One must-see attraction in the vicinity is the Lake Cumberland State Resort Park, which features beautiful trails and picnic areas, great for enjoying the great outdoors. Additionally, the nearby Wolf Creek Dam is an impressive site worth visiting, offering stunning views and informative tours about the dam's history and significance.
How much does it cost to rent a holiday home in Jamestown?
Prices for holiday rentals in Jamestown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Jamestown to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Jamestown holiday house rentals?
You can find great discounts on house rentals in Jamestown on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Jamestown?
In Jamestown, holiday houses are the most popular type of accommodation, with approximately 32 available throughout the area. These houses typically feature spacious layouts, including multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios, making them ideal for families or groups looking to enjoy the scenic beauty of nearby Lake Cumberland. Additionally, there are around 30 cabins that provide a rustic charm, often situated in wooded areas, offering amenities like fireplaces and outdoor fire pits for evening gatherings. Cottages, while fewer in number at about 16, also provide a cosy atmosphere and are often found near local attractions. Several apartments and condos are available as well, though they are less common.
Are there any family house rentals in Jamestown?
In Jamestown, Kentucky, there are numerous family-friendly house rentals available—specifically, around 69 options scattered throughout the area. This charming town offers a range of accommodations suitable for families, often featuring spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces for children to enjoy. Many properties are conveniently located near Lake Cumberland, which provides ample opportunities for boating, fishing, and swimming. See all family-friendly rentals in Jamestown.
Can I rent a holiday home with a pool or hot tub in Jamestown?
In Jamestown, Kentucky, there are several holiday homes available for rent that feature pools or hot tubs, with around 17 options to choose from. This picturesque area near Lake Cumberland offers a variety of properties, many of which are situated in tranquil neighbourhoods ideal for a relaxing getaway. Travellers can expect amenities such as private swimming pools, outdoor hot tubs, and spacious decks for entertaining or unwinding in the fresh air. Many rentals also include fully equipped kitchens, making it convenient for families or groups to prepare meals together. Find your rental in Jamestown with a pool or a hot tub.
Can I find long-stay holiday rentals in Jamestown?
A long-stay holiday rental in Jamestown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Jamestown?
In Jamestown, Kentucky, there are a variety of pet-friendly house rentals available, with around 49 options to choose from. Many of these holiday homes come equipped with essential amenities such as fully furnished kitchens, spacious living areas, and outdoor spaces where pets can roam.

The area is particularly appealing for pet owners due to its proximity to picturesque natural spots, including Lake Cumberland, which offers ample opportunities for outdoor activities like hiking, fishing, and boating with your furry companions. Additionally, the nearby Daniel Boone National Forest provides numerous trails and scenic views, making it a great place for leisurely strolls with pets. See all pet-friendly rentals in Jamestown.
Are there any remote work holiday rentals in Jamestown?
In Jamestown, Kentucky, there are numerous remote work holiday rentals available, with around 81 options to choose from. This charming town, located near Lake Cumberland, provides an ideal setting for those looking to balance work and leisure. Many properties feature dedicated workspaces, including desks and comfortable chairs, along with reliable Wi-Fi to ensure productivity during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Jamestown holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Jamestown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Jamestown?
In Jamestown, popular holiday rentals typically feature amenities that enhance comfort and convenience for guests. Most properties come equipped with a kitchen, which includes essential appliances such as a microwave, stovetop, and refrigerator. Guests can also expect cookware, dishware, and utensils, allowing for self-catering during their stay.
When is the best time to visit Jamestown for a holiday rental?
The best time to visit Jamestown for a holiday rental is during the peak season from May to July, when the charm of Kentucky truly comes alive. This period sees a surge in tourists eager to explore the picturesque lakes, hiking trails, and local attractions that make Jamestown a hidden gem for outdoor enthusiasts.

Among these months, July stands out as particularly popular, offering warm temperatures averaging around 30°C. This inviting climate creates the superb backdrop for activities such as boating on Lake Cumberland, fishing, and enjoying the local festivals that fill the calendar. The vibrant atmosphere and the opportunity to connect with fellow travellers enhance the overall experience.

If you're looking for a more budget-friendly option, consider visiting in November. This month, while quieter, provides a unique opportunity to experience the stunning autumnal landscapes without the hustle and bustle of peak season. The fall foliage adds a beautiful touch to the area's natural scenery, making it ideal for peaceful hikes and scenic drives.
How early should I book a Jamestown holiday rental?
Book your Jamestown holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Jamestown home rental booking on Vrbo?
To find Jamestown holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Jamestown holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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