Photo by Susie Edwards

Jamestown vacation rentals

We found 170 vacation rentals — enter your dates for availability

Discover a selection of 34 homes, 39 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.

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Find out more about Jamestown

Why visit Jamestown

  • Outdoor Adventures: Enjoy thrilling activities at Jamestown Marina, including boat rentals and lakeside fun.
  • Scenic Parks: Explore nearby national and state parks, perfect for family outings and nature walks.
  • Charming Accommodations: Choose from cozy cabins and charming cottages for a delightful stay.
  • Welcoming Community: Experience the friendly atmosphere and hospitality from local residents.
  • Relaxing Getaway: Unwind in the picturesque surroundings, ideal for a romantic escape or family vacation.

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 charming cottage, we have the perfect accommodation for your getaway. Explore the best cabins in Jamestown or enjoy the scenic beauty with Lake Cumberland cabin rentals. Whatever your preference, our home rentals offer transparency and savings, ensuring a delightful stay in this picturesque destination.

  • Houses: The top choice for travelers, these homes offer spacious accommodations perfect for families, friends, or couples seeking comfort and privacy.
  • Cabins: A favorite among nature enthusiasts, cabins provide a rustic and serene escape amidst the beautiful landscape of Jamestown.
  • Cottages: These charming, quaint spaces are ideal for a cozy getaway, perfect for couples or small families.
  • Chalets: Offering a unique blend of style and comfort, chalets are great for those who appreciate a scenic mountain feel.
  • Condos: A practical option for travelers, condos combine convenience with amenities, making them a popular choice for those wanting a home-like feel.**

Top attractions in Jamestown

Jamestown, Kentucky, is an ideal destination for outdoor enthusiasts and those seeking a romantic getaway, offering stunning scenery and various attractions. Visitors can enjoy the Jamestown Marina, Safe Harbor Jamestown, and boat rentals for a lakeside adventure. With its parks and nearby national and state parks, Jamestown provides plenty of opportunities for family fun and beach experiences, making it a perfect spot for a memorable vacation.

  • Lake Cumberland State Resort Park: Experience stunning natural beauty with scenic views, hiking trails, and opportunities for outdoor adventures like fishing and boating. The park offers a perfect escape for nature lovers.
  • Wolf Creek National Fish Hatchery: Discover eco-friendly practices and learn about fish conservation efforts. This center provides a unique opportunity to see fish rearing processes and interacts with educational programs focused on environmental stewardship.
  • Jamestown Marina: Enjoy a vibrant atmosphere with beach access and thrilling water activities. Rent a boat, go fishing, or relax by the shore while soaking in the sun and scenic lake views.

Things to do recommended for couples

Jamestown offers a charming getaway for couples. Explore the scenic beauty of Lake Cumberland with a sunset boat rental, or enjoy a romantic picnic at the local parks. Don't forget to visit the quaint shops downtown for unique souvenirs to remember your trip together.

Things to do recommended for families

Families will love exploring Lake Cumberland State Resort Park, where they can enjoy hiking, fishing, and picnicking. A visit to the nearby Jamestown Marina offers boat rentals for a fun day on the water, perfect for creating lasting memories together.

Things to do recommended for groups

Explore the scenic beauty of Lake Cumberland with a group boat rental or enjoy a fun-filled day at the Jamestown Marina. Don’t miss the chance to visit the local shops and sample delicious Southern cuisine at nearby restaurants for a memorable experience.

*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 an extended stay, be sure to prioritize your filters accordingly. 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 full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Jamestown with young kids: Traveling with young kids can be difficult. It’s important to prioritize their comfort and safety, as well as access to suitable amenities like a private swimming pool. Additionally, keeping in mind your closeness to family-friendly attractions can enhance the experience.
  • Taking your pets with you to Jamestown: For many families, a vacation isn't truly complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and 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 that offer 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 include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Jamestown

Jamestown, Kentucky, offers a delightful blend of outdoor adventures and scenic beauty, perfect for a romantic getaway or family-friendly vacation. Explore diverse habitats along Pumpkin Creek, where friendly locals welcome you to experience the warm atmosphere of this charming city. Nearby regions provide additional opportunities for relaxation and exploration, making Jamestown an ideal base for your Kentucky adventure.

  • Lake Cumberland: Nestled about 7 miles from Jamestown, Lake Cumberland is a stunning natural retreat known for its expansive waters and lush surroundings. This picturesque lake is perfect for outdoor enthusiasts seeking adventure and romance. Visitors can enjoy a variety of recreational activities such as hiking along scenic trails, camping in serene areas, and exploring the beautiful state park that surrounds the lake. With its breathtaking views and tranquil atmosphere, Lake Cumberland is an ideal spot for a memorable getaway.
  • Russell Springs: Located just 5 miles from Jamestown, Russell Springs is a charming city that attracts travelers with its scenic beauty and outdoor offerings. The city is a gateway to various recreational areas, making it easy for visitors to immerse themselves in nature. Enjoy leisurely hikes along well-maintained trails, relax at local campgrounds, and explore the nearby state park. The area's natural landmarks, including the stunning lake, provide ample opportunities for romantic outings and family fun alike.
  • Eli: A quaint village situated 7 miles from Jamestown, Eli is a hidden gem for those seeking outdoor adventures and serene beach experiences. The village boasts a welcoming atmosphere and offers a range of activities for nature lovers. Visitors can explore recreational areas and enjoy the scenic beauty of the local marina. Eli’s access to the lake and urban park creates a perfect backdrop for leisurely days spent picnicking or taking in the stunning vistas, making it an excellent choice for relaxation and exploration.

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 simple

Are you eager to save on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices can fluctuate. Additionally, booking a longer stay often leads to considerable savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect option for your needs.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner has its perks. When you enroll in our travel rewards program, One Key, you’ll gain immediate access to exclusive member savings and can earn and redeem OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a convenient way for you to plan your trips. You can start new trips, pick up where you left off, or easily view and organize your travel plans. All the properties you've saved and booked are now categorized into Potential, Upcoming, or Current Trips for your convenience. To explore 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)
  • Lowgap Island (5.6 mi / 8.9 km)
  • Wolf Creek Recreation Area (7.3 mi / 11.7 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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