The Dock House Lake Retreat – Family-Friendly with Private River Access

- Location: Jamestown
- Guest rating: 9/10 (Wonderful, 8 reviews)
- Price: $137 (was $150, 8% off), $962 for 7 nights, All fees included

We found 216 vacation rentals — enter your dates for availability
Welcome to the enchanting charm of Jamestown, where stunning lake views and lush parks create the perfect backdrop for your next getaway. Dive into thrilling outdoor adventures at Jamestown Marina or explore scenic trails in nearby state parks, making it an ideal destination for families and groups alike. Choose from cozy cabins and charming cottages that offer space and comfort, ensuring a delightful home-like experience while you immerse yourself in this welcoming community.

















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Condo/Apartment
Cabin
Cottage
Villa
Chalet

1

Premier Host
Sleeps 16 · 5 bedrooms · 3+ bathrooms

Premier Host
Sleeps 14 · 4 bedrooms · 2+ bathrooms

Premier Host
Sleeps 8 · 3 bedrooms · 3 bathrooms

Premier Host
Sleeps 12 · 3 bedrooms · 2 bathrooms

Premier Host
Sleeps 8 · 3 bedrooms · 1+ bathroom

Premier Host
Sleeps 6 · 3 bedrooms · 2 bathrooms
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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.
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.
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.
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.
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.
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.
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.
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.
| Calendar Month | Temperature | Precipitation | Cloudiness | Occupancy | Pricing |
| January | 35.2°F (1.8°C) | Light Rain | Mostly Cloudy | Moderately Low | Slightly Low |
| February | 39.6°F (4.2°C) | Light Rain | Mostly Cloudy | Average | Slightly Low |
| March | 47.7°F (8.7°C) | Light Rain | Mostly Cloudy | Average | Slightly Low |
| April | 56.5°F (13.6°C) | Light Rain | Mostly Sunny | Average | Average |
| May | 65.8°F (18.8°C) | Light Rain | Mostly Sunny | Moderately High | Average |
| June | 73.6°F (23.1°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High |
| July | 76.5°F (24.7°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High |
| August | 75.0°F (23.9°C) | Light Rain | Mostly Sunny | Average | Slightly High |
| September | 69.3°F (20.7°C) | Light Rain | Mostly Sunny | Average | Average |
| October | 58.5°F (14.7°C) | Light Rain | Mostly Sunny | Average | Average |
| November | 47.1°F (8.4°C) | Light Rain | Mostly Sunny | Moderately Low | Average |
| December | 41.0°F (5.0°C) | Light Rain | Mostly Cloudy | Moderately Low | Average |
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.
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**Based on Vrbo properties bookings.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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.
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