Jamestown vacation rentals

We found 165 vacation rentals — enter your dates for availability

Discover a selection of 34 homes, 36 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:Dec 5 - Dec 12

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Harbor Springs, Lake Cumberland Cabin

Jamestown, KY

16% off
Price is $279
$1,956 for 7 nights
All fees included
Harbor Springs, Lake Cumberland Cabin

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Find out more about Jamestown

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:

  • Lake Cumberland Winery (12.4 mi / 19.9 km)
  • Dale Hollow Lake State Resort Park Golf Course (25.8 mi / 41.6 km)
  • Up the Creek Winery (22.6 mi / 36.4 km)
  • The Links Resort Golf Course (1.3 mi / 2.1 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)
  • Mountain View Park (19 mi / 30.6 km)

Frequently asked questions

What is the best area to stay in Jamestown when booking a vacation rental?
When planning a vacation in Jamestown, Kentucky, one of the best areas to consider for your rental stay is the vicinity around the beautiful Lake Cumberland. This area is particularly popular among visitors due to its stunning waterfront views and easy access to a variety of outdoor activities. You'll find a good selection of vacation rentals here, suiting families, couples, and groups looking to enjoy a relaxing getaway.

Staying near Lake Cumberland puts you just a short distance from popular attractions such as the Lake Cumberland State Resort Park, which offers hiking trails, fishing, and boating opportunities. Another highlight in this area is the Wolf Creek Dam, an engineering marvel that provides scenic viewpoints and great spots for photography. The natural beauty surrounding the lake, coupled with the recreational activities available, makes this area an excellent choice for those looking to immerse themselves in nature while enjoying the comforts of a vacation rental.

Additionally, the local community is friendly and welcoming, making it easy to feel at home during your stay.
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.
Where are the best areas for renting a beach house in Jamestown?
For renting a beach house in Jamestown, Kentucky, travelers should focus on the beautiful shoreline of Lake Cumberland, which is known for its clear waters and recreational opportunities. The area around Lake Cumberland State Resort Park offers various vacation rentals with amenities such as private docks, outdoor grilling areas, and spacious decks that provide stunning views of the lake. Many of these properties include access to the park's facilities, which feature hiking trails, picnic areas, and a swimming beach.

Additionally, the neighborhoods near the Jamestown Marina are ideal for those looking for beach houses, as they often have direct access to boat rentals and fishing spots. Rentals in this vicinity typically come with modern conveniences such as fully equipped kitchens, air conditioning, and some even offer private hot tubs for relaxation after a day of outdoor activities.

For travelers interested in a more secluded experience, the areas further along the lake's shoreline boast cabins and cottages located among lush forests, which provide a tranquil escape while still being close to the water. Many of these properties come with amenities like fire pits, game rooms, and outdoor seating areas, great for family gatherings or romantic getaways. Find your rental near the beach in Jamestown.
What is the most popular type of vacation rental accomodation in Jamestown?
In Jamestown, vacation houses are the most popular type of rental accommodation, with around 34 available throughout the area. These homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios, great for enjoying the scenic views of nearby Lake Cumberland. Additionally, there are about 29 cabins, which offer a rustic charm and often include amenities like fireplaces and hot tubs, ideal for families or groups seeking a cozy retreat in nature. For those looking for a more compact option, around 15 cottages are also available, providing a quaint setting with essential amenities. Several condos and apartments can be found as well, suiting travelers who prefer a smaller space while still being close to local attractions and outdoor activities.
Are there any family house rentals in Jamestown?
In Jamestown, Kentucky, there are numerous family-friendly house rentals available, with around 65 options to choose from. The area is known for its beautiful landscapes and proximity to attractions such as Lake Cumberland, which is superb for outdoor activities like boating, fishing, and swimming. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor patios or decks where guests can relax and enjoy the scenery.

Visitors will find that some properties come with amenities like game rooms or private yards, providing entertainment for children and a comfortable environment for family gatherings. Additionally, being close to local parks and nature trails makes it easy for families to engage in hiking or picnicking, ensuring a memorable stay in this charming locale. See all family-friendly rentals in Jamestown.
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 and hot tubs, with around 19 options to choose from. This charming town, located near Lake Cumberland, provides a picturesque setting for travelers looking to relax and enjoy water activities. Many of these rentals come equipped with private pools and hot tubs, along with spacious outdoor areas superb for family gatherings or barbecues. Inside, visitors can expect modern amenities such as fully equipped kitchens, comfortable living spaces, and often multiple bedrooms, making them ideal for families or groups. Find your rental in Jamestown with a pool or a hot tub.
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, Kentucky, there are numerous pet-friendly house rentals available, offering a variety of amenities to accommodate travelers with pets. Many of these homes feature spacious yards, making them ideal for pets to roam freely. Inside, you can expect comfortable living spaces, fully equipped kitchens, and cozy bedrooms, superb for relaxation after a day of exploring the area.

The Jamestown area is known for its proximity to Lake Cumberland, where outdoor enthusiasts can enjoy activities such as fishing, boating, and hiking. Several vacation rentals are conveniently located near the lake, providing easy access to waterfront activities. Additionally, the surrounding natural beauty and nearby parks make it a great spot for walking your pet and enjoying the outdoors. See all pet-friendly rentals in Jamestown.
Are there any remote work vacation rentals in Jamestown?
In Jamestown, Kentucky, there are numerous options for remote work vacation rentals, with about 73 properties available. Many of these rentals cater specifically to remote workers, offering amenities that facilitate productivity. Expect to find accommodations equipped with reliable Wi-Fi, dedicated desks, desk chairs, and laptop workspaces, ensuring that you can work comfortably during your stay.

The area is known for its scenic beauty, being close to Lake Cumberland, which provides opportunities for outdoor activities during breaks from work. You'll find various rental types, from cozy cabins to larger homes, often featuring outdoor spaces where you can unwind after a day of work. 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, popular vacation rental amenities include WiFi, kitchens, blenders, coffee and tea makers, and patios. Travelers can expect to find properties that allow for a comfortable and convenient stay, with kitchens equipped for preparing meals, cozy living spaces for relaxation, and outdoor patios for enjoying the serene surroundings.
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 period is particularly popular among travelers seeking outdoor adventures and family-friendly activities, as the warm summer temperatures typically range from the low 60s to mid-80s Fahrenheit. The vibrant atmosphere during these months offers plenty of opportunities for boating, fishing, and hiking at nearby Lake Cumberland State Resort Park, where families can enjoy a variety of water sports and scenic trails.

July stands out as the most favored month to visit, bringing together a lively mix of visitors eager to experience the local charm and attractions. The town comes alive with summer events, making it an excellent time for those who enjoy socializing and exploring at a bustling pace.

For those looking for a more budget-friendly option, consider planning your trip in November. This month provides a quieter experience, where you can appreciate the serene beauty of the area, including the stunning fall foliage without the summer crowds.
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?
In Jamestown, Kentucky, visitors can enjoy a variety of attractions centered around the natural beauty of the area. Lake Cumberland is a major draw, offering opportunities for boating, fishing, and swimming, with several waterfront parks and marinas located nearby. The Jamestown Marina is a popular spot for those looking to rent boats or take part in water activities.

In the downtown area, travelers can explore local shops and eateries that showcase the charm of this small town. The nearby Wolf Creek Dam provides scenic views and picnic areas, making it a great place for outdoor recreation. For history enthusiasts, the area is also known for its connections to the region's pioneer past, with historical markers and sites to visit that detail Jamestown's rich heritage.
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 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 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.

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