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Jamestown vacation rentals

We found 169 vacation rentals — enter your dates for availability

Discover a selection of 35 homes, 40 cabins, and other vacation rentals in Jamestown that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include WiFi and a fireplace. What you'll find is a rental that has what everyone needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Jamestown

Showing deals for:May 15 - May 22

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 $139
$975 for 7 nights
All fees included
The Little Hideaway at Beaver Creek (1 mile from Beaver Creek Marina)

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Find out more about Jamestown

Why visit Jamestown

  • Scenic Lake Cumberland: Enjoy breathtaking views and a charming lakeside landscape perfect for relaxation and recreation.
  • Outdoor Activities: Engage in various outdoor adventures like hiking, boating, and fishing in the surrounding state and local parks.
  • Family-Friendly Environment: Experience a welcoming atmosphere ideal for family getaways and memorable adventures.
  • Diverse Accommodations: Choose from cozy cabins, private homes, or quaint cottages that cater to different preferences.
  • Local Charm: Discover the friendly locals and vibrant community that enhance your visit to Jamestown.

Popular types of accommodation in Jamestown

Discover the charm of Jamestown with our diverse selection of vacation rentals. Whether you're seeking a cozy cabin, a private vacation home, or a quaint cottage, we have the perfect spot for you. Enjoy the serene beauty of Lake Cumberland and find safe harbor in our trusted accommodations. Explore the best house rentals in Jamestown and make unforgettable memories with your loved ones.

  • Houses: These are the top choice for travelers looking for a spacious and comfortable stay in Jamestown, perfect for families or groups.
  • Cabins: A favorite among nature lovers, these cozy retreats offer an authentic rustic experience amidst the beautiful surroundings of Jamestown.
  • Cottages: Ideal for a charming getaway, these quaint accommodations provide a homey atmosphere close to local attractions.
  • Chalets: These unique, often elevated lodgings combine comfort and stunning views, making them a delightful option for visitors.
  • Condos: Offering convenience and amenities, condos are a popular choice for those wanting easy access to the area's attractions.**

Top attractions in Jamestown

Jamestown, Kentucky, is perfect for outdoor enthusiasts seeking scenic adventures. Visitors can explore a variety of attractions, including marinas, state parks, and local parks. These points of interest provide a range of experiences suitable for families and those looking to enjoy the beach and nature. Whether you're into water activities or enjoying a family day out, Jamestown has something to offer for everyone.

  • Lake Cumberland State Resort Park: This stunning park offers breathtaking scenery and a range of outdoor adventures, from hiking trails to fishing spots. Enjoy the serene vibes and immerse yourself in nature's beauty.
  • Wolf Creek National Fish Hatchery: A unique eco-friendly destination, this hatchery showcases sustainable practices and provides insights into aquatic life. It's a great spot for nature lovers and those interested in conservation efforts.
  • Jamestown Marina: Experience the thrill of water activities at this lively marina. With beach vibes and opportunities for boating, fishing, and relaxing by the water, it's perfect for adventure seekers.

Things to do recommended for couples

Ready for a romantic getaway in Jamestown? Visit Lake Cumberland Winery, located 12 miles away, where you can savor fine wines in a charming atmosphere. Enjoy the entertainment and create lasting memories together amidst the picturesque surroundings.

Things to do recommended for families

Families can explore the beauty of Lake Cumberland, enjoy fishing or boating, and visit the nearby Wolf Creek Dam for stunning views. Kids will love the local parks and the fun at the Jamestown Marina, making it a perfect destination for family-friendly activities.

Things to do recommended for groups

Groups visiting Jamestown can enjoy a round of golf at The Links Resort Golf Course, which offers a beautiful outdoor setting perfect for friendly competition and relaxation amidst nature. This local gem is ideal for bonding and creating memorable moments together.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Jamestown

If you're traveling with a group, family, pets, or planning for extended stays, be sure to use the right filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Jamestown with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group activities. Thankfully, you can easily narrow down your options for these and many other amenities on Vrbo.
  • Traveling to Jamestown with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Jamestown: For many, a family vacation wouldn't be the same without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Jamestown: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider including amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Jamestown

Jamestown, Kentucky, is the perfect destination for outdoor enthusiasts and families alike. Nestled by the stunning Lake Cumberland, visitors can enjoy breathtaking scenic views and a charming lakeside landscape. The friendly atmosphere and welcoming locals make it an ideal spot for a family getaway or an adventurous vacation. Explore the nearby regions for more family-friendly experiences, ensuring a memorable trip filled with adventure and relaxation.

  • Lake Cumberland: Lake Cumberland is a stunning natural destination located 7 miles from Jamestown, known for its expansive lake and breathtaking scenery. This area is a haven for outdoor enthusiasts, offering a plethora of activities such as hiking, camping, and exploring the recreational areas surrounding the lake. Whether you're looking to relax by the water, embark on an adventurous hike, or enjoy a picnic in the national state park, Lake Cumberland provides a perfect backdrop for nature lovers. Don't miss the chance to experience the tranquil beauty of this iconic Kentucky lake.
  • Russell Springs: Situated just 5 miles from Jamestown, Russell Springs is a charming city that invites visitors to enjoy its picturesque landscapes and outdoor experiences. Known for its romantic ambiance, this area is ideal for couples seeking a serene getaway. Russell Springs offers excellent hiking trails and campgrounds that allow you to immerse yourself in nature. The nearby lake and national state park serve as perfect spots for fishing, boating, or simply enjoying a peaceful day outdoors. With its small-town charm and beautiful scenery, Russell Springs is a delightful destination.
  • Eli: Eli, a quaint village located 7 miles from Jamestown, is perfect for those looking to escape into nature while enjoying a sense of adventure. This area boasts recreational areas and resorts that cater to outdoor enthusiasts and families alike. Visitors can explore the nearby national state park, hike picturesque trails, or relax at the lake. Eli's serene environment, combined with its unique monuments, offers a perfect blend of adventure and tranquility, making it an excellent choice for a memorable vacation experience.

Best time to go to Jamestown

If you're planning a trip to Jamestown, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from May to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.2°F (1.8°C)Light RainMostly CloudyModerately LowSlightly Low
February39.6°F (4.2°C)Light RainMostly CloudyAverageSlightly Low
March47.7°F (8.7°C)Light RainMostly CloudyAverageSlightly Low
April56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
May65.8°F (18.8°C)Light RainMostly SunnyModerately HighAverage
June73.6°F (23.1°C)Light RainMostly SunnyModerately HighSlightly High
July76.5°F (24.7°C)Light RainMostly SunnyModerately HighSlightly High
August75.0°F (23.9°C)Light RainMostly SunnyAverageSlightly High
September69.3°F (20.7°C)Light RainMostly SunnyAverageAverage
October58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
November47.1°F (8.4°C)Light RainMostly SunnyModerately LowAverage
December41.0°F (5.0°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is a breeze

Are you hoping to cut costs on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your travel needs.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your complete booking. It truly benefits you to take on the planning role. When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and accumulate OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's groundbreaking Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily manage your travel arrangements. You can now find your previously saved and booked properties categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the lakeside landscape of Jamestown

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

Sightseeing in and around Jamestown

Do you want to discover attractions to visit in the area? Venture out of your cozy vacation rental and experience everything that makes Jamestown a one-of-a-kind vacation spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 an adventurous traveler or just want to appreciate the scenery, Jamestown is a great place to get out in nature. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • 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, Kentucky, United States of America when booking a vacation rental?
When looking for the best area to stay in Jamestown, Kentucky, consider the charming neighborhoods around the scenic Lake Cumberland. This area is known for its natural beauty and outdoor recreational opportunities, making it an ideal choice for vacation rentals. You'll find a variety of properties ranging from cozy cabins to lakeside homes, allowing you to enjoy the serene environment.

One of the top attractions in this region is Lake Cumberland State Resort Park, where you can indulge in activities such as boating, fishing, and hiking. The park offers stunning views and plenty of trails to explore, making it great for nature enthusiasts. Additionally, the nearby Wolf Creek Dam is a point of interest for those fascinated by engineering and the great outdoors, providing educational tours and breathtaking vistas.
How much does it cost to rent a vacation home in Jamestown?
Prices for vacation 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 vacation 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 vacation rental accomodation in Jamestown?
In Jamestown, cabins are the most popular type of vacation rental, with about 38 available throughout the area. These rustic properties often feature cozy interiors, fully equipped kitchens, and spacious living areas, making them superb for families or groups looking to enjoy a peaceful retreat near Lake Cumberland. Many cabins also include outdoor decks or porches where guests can relax and take in the natural surroundings.

Additionally, there are around 35 vacation houses, which provide similar amenities and comfort, with some even offering private yards and BBQ facilities for outdoor gatherings. For those seeking a quaint experience, about 14 cottages can also be found, often located in quieter neighborhoods, offering a charming atmosphere. While there are several apartments and condos, they are less common compared to cabins and vacation houses.
Can I rent a vacation home with a pool or hot tub in Jamestown?
In Jamestown, Kentucky, there are several vacation homes available for rent that feature pools, with around 19 options to choose from. This charming area near Lake Cumberland is an excellent destination for those seeking relaxation and outdoor activities. Many of these properties come equipped with private pools, outdoor seating areas, and spacious backyards, superb for family gatherings or a peaceful retreat. Additionally, travelers can expect amenities such as fully equipped kitchens, comfortable living spaces, and sometimes even hot tubs for added luxury.
Can I find long-stay vacation rentals in Jamestown?
A long-stay vacation rental in Jamestown is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Jamestown?
In Jamestown, there are numerous pet-friendly house rentals available, providing travelers with a variety of options for their stay. Many of these properties come equipped with modern amenities such as fully equipped kitchens, outdoor spaces, and cozy living areas, making them comfortable for both humans and their furry companions.

The area around Lake Cumberland is particularly attractive, with vacation rentals offering easy access to the water and surrounding natural beauty. Some homes feature private docks, patios, and fire pits, ideal for enjoying evenings outdoors.

Additionally, the nearby state parks and recreational areas provide ample opportunities for outdoor activities with pets, including hiking and fishing.
Are there any remote work vacation rentals in Jamestown?
In Jamestown, Kentucky, there are numerous remote work vacation rentals available, with around 87 options to choose from. This charming town offers a peaceful setting ideal for remote work, complemented by various amenities that cater to professionals. Many rentals feature reliable internet access, often provided through third-party services, and free Wi-Fi in the rooms.

Travelers can expect comfortable accommodations that include spacious work areas and the flexibility to conduct meetings or focus on tasks without interruption. Additionally, some properties permit events, allowing for collaborative workspaces if needed. The serene surroundings of Jamestown also provide a refreshing backdrop for work-life balance, with local attractions such as Lake Cumberland nearby for leisure during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Jamestown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Jamestown with parking available—perfect for families or travelers 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, vacation rentals typically feature a range of amenities that enhance the stay for travelers. Most properties come equipped with a kitchen, allowing guests to prepare their own meals, which is particularly convenient for families or groups. Onsite parking is commonly available, making it easy for visitors to arrive and explore the area. Many rentals also include a deck or patio, providing a lovely outdoor space to relax and enjoy the surrounding scenery. Additional amenities often found in these rentals include a blender for making smoothies or other beverages, and a coffee and tea maker to kickstart the day.
When is the best time to visit Jamestown for a vacation rental?
The best time to visit Jamestown for a vacation rental is during the peak season from May to July. This vibrant period attracts travelers eager to enjoy the outdoor adventures that Kentucky's beautiful landscapes offer. With the warm summer sun shining down, visitors can enjoy various activities such as boating on Lake Cumberland, hiking in nearby state parks, and exploring the charming local shops and dining options.

July stands out as the most popular month, where the lively option buzzes with fellow adventurers and families. Expect temperatures in the mid-70s to mid-90s Fahrenheit, providing ample opportunities for outdoor fun, whether it's fishing, kayaking, or simply soaking up the sun at one of the area's pristine beaches.

For those looking for a more budget-friendly experience, consider visiting in November. This quieter month allows you to enjoy the beautiful fall scenery, with the changing leaves providing a picturesque backdrop for leisurely strolls and scenic drives. Plus, you'll find that accommodation prices tend to be more favorable during this time.
How early should I book a Jamestown vacation rental?
Book your Jamestown vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Jamestown, Kentucky, United States of America?
In Jamestown, Kentucky, visitors can enjoy a variety of attractions centered around the beautiful Lake Cumberland, which is superb for boating, fishing, and water sports. The nearby Lake Cumberland State Resort Park offers stunning natural scenery, hiking trails, and picnic areas, making it an excellent spot for outdoor enthusiasts.

Another popular site is the historic Jamestown Square, where travelers can find charming shops and local eateries that highlight the region's culture and hospitality. The area also features the Wolf Creek Dam, which provides educational tours and impressive views of the surrounding landscape. For those interested in history, the nearby home of the late author and local legend, which is often included in tours, adds a cultural dimension to the visit.
Can I change or cancel my Jamestown home rental booking on Vrbo?
To find Jamestown vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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