Photo by Susie Edwards

Jamestown holiday lettings

We found 170 holiday rentals — enter your dates for availability

Discover a selection of 35 homes, 40 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:22 May - 29 May

Image gallery for The Little Hideaway at Beaver Creek (1 mile from Beaver Creek Marina)

10 out of 10, Exceptional, (42 reviews)
Exceptional
(42 reviews)

The Little Hideaway at Beaver Creek (1 mile from Beaver Creek Marina)

Monticello

8% off
Price is £799
for 7 nights, 1 cabin
£114 per night
includes taxes & fees
The Little Hideaway at Beaver Creek (1 mile from Beaver Creek Marina)

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:

  • Dale Hollow Lake State Resort Park Golf Course (25.8 mi / 41.6 km)
  • Lake Cumberland Winery (12.4 mi / 19.9 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)
  • Cumberland Point Recreation Area (12.3 mi / 19.7 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 Lake Cumberland area stands out as an excellent choice. This picturesque region is renowned for its stunning lake views and outdoor recreational opportunities, making it a favourite among visitors. You'll find a variety of properties available, from charming cabins to modern houses, providing plenty of options to suit different tastes and budgets.

One of the top attractions in the vicinity is Lake Cumberland itself, which offers a myriad of activities such as boating, fishing, and hiking. The area is also home to the beautiful Wolf Creek Dam, where you can enjoy scenic walks and learn about the engineering marvel while taking in the breathtaking surroundings.

Additionally, the nearby town centre provides a quaint setting with local shops and dining options, great for exploring the community.
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, cabins are the most popular type of holiday rental, with around 114 available throughout the area. Nestled in picturesque settings, these cabins provide a rustic charm and often feature amenities like fully equipped kitchens, spacious living areas, and outdoor decks or porches for enjoying the serene views. They are superb for travellers seeking a tranquil escape close to nature.

Holiday houses are also quite common, with about 105 options offering more spacious rooms, ideal for families or larger groups. These homes typically come with multiple bedrooms, private gardens, and amenities such as BBQ facilities, allowing guests to enjoy outdoor gatherings. Additionally, there are around 42 cottages and a few condos and apartments, which cater to those looking for a quaint and comfortable stay.
Are there any family house rentals in Jamestown?
In Jamestown, Kentucky, there are numerous family-friendly house rentals available, with about 68 options to choose from. The area is known for its beautiful landscapes and proximity to Lake Cumberland, making it an ideal spot for families seeking outdoor adventures. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces for children to play or for family barbecues.

Visitors can enjoy nearby attractions such as the Lake Cumberland State Resort Park, which offers hiking trails, fishing opportunities, and stunning views of the lake. Additionally, the town's charming atmosphere is complemented by local shops and eateries that provide a taste of the region's hospitality.
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 come equipped with pools or hot tubs, with around 19 options to choose from. This charming town is situated near Lake Cumberland, making it an attractive destination for those looking to enjoy water activities alongside a relaxing stay.

Travellers can expect a variety of amenities in these rentals, including private swimming pools, hot tubs for unwinding after a day of exploration, and spacious outdoor areas ideal for gatherings. Many properties also feature fully equipped kitchens, allowing guests to prepare their own meals while enjoying the comforts of home.
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 numerous pet-friendly house rentals available, with a total of 54 options to choose from. Many of these holiday homes come equipped with amenities like spacious backyards, which are great for pets to roam, as well as fully equipped kitchens and comfortable living areas for relaxation after a day of exploring.

The area is well-suited for pet owners, as it offers various outdoor activities. Nearby, you can find the beautiful Lake Cumberland, where you can enjoy boating and fishing, and some properties may even offer easy access to the water. Additionally, the surrounding countryside provides plenty of opportunities for hiking and walking trails, making it an ideal getaway for those looking to enjoy nature with their furry companions.
Are there any remote work holiday rentals in Jamestown?
In Jamestown, Kentucky, there are numerous options for remote work holiday rentals, with around 261 properties available to choose from. This charming town offers a variety of accommodations that cater to those who need to balance work with leisure. Many of these rentals are equipped with essential amenities such as free Wi-Fi and high-speed internet, ensuring a smooth working experience.

Travellers can expect comfortable living spaces that often include dedicated work areas, along with fully equipped kitchens for self-catering. Additionally, some properties may feature outdoor spaces where guests can unwind after a day of work.

Jamestown is located near Lake Cumberland, providing a picturesque backdrop for those looking to enjoy outdoor activities during their downtime. The area is known for its boating, fishing, and hiking opportunities, making it ideal for both work and relaxation. 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 rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also offer onsite parking, making it convenient for travellers with vehicles. Furthermore, rentals often feature decks or patios, providing outdoor spaces to enjoy the pleasant surroundings. Additional amenities such as blenders and coffee or tea makers are typically included, ensuring guests can enjoy their favourite beverages during their stay.
When is the best time to visit Jamestown for a holiday rental?
The peak season for visiting Jamestown, Kentucky, runs from May to July, with July being the most popular month for holiday rentals. This vibrant timeframe attracts families and adventure seekers eager to explore the picturesque Lake Cumberland, renowned for its stunning views and ample recreational opportunities. Visitors can enjoy everything from boating and fishing to hiking along the scenic trails that surround the lake.

During July, temperatures typically reach pleasant levels, hovering around 25 to 30 degrees Celsius, making it ideal for outdoor activities and water sports. The warm weather creates a lively option, with many events and festivals that celebrate the local culture and community spirit.

For those looking for more affordable options, visiting in November might be appealing. This month offers a quieter experience as the summer crowds have dispersed, allowing for serene walks by the lake and a chance to appreciate the tranquil beauty of the changing seasons.
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.
What are the top attractions in Jamestown?
In Jamestown, Kentucky, visitors can enjoy a variety of attractions that showcase the area's natural beauty and rich history. The Lake Cumberland area is a major draw, offering a stunning backdrop for outdoor activities such as boating, fishing, and hiking. Nearby, the beautiful State Dock provides access to the lake, with opportunities for water sports and relaxing by the shore.

The historic downtown area features charming shops and local eateries, great for exploring the local culture. For those interested in history, the Jamestown Historical Society offers insights into the town's past and hosts events throughout the year. Additionally, the nearby Wolf Creek Dam is an engineering marvel, with scenic views and walking trails around the reservoir, making it a great spot for a leisurely stroll or picnic.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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