Discover a selection of 105 vacation rentals in Jamestown, KY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $125 per night, and houses and cabins are popular options for a stay in Jamestown. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Jamestown
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Destination guide

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.

Things to do

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)
Natural features

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)
  • Dale Hollow Reservoir (29.9 mi / 48.2 km)
  • Wolf Creek National Fish Hatchery (9 mi / 14.5 km)
  • Green River Lake (21.8 mi / 35.2 km)
  • Dale Hollow Lake State Park (26.5 mi / 42.7 km)
  • Zollicoffer Park (18.5 mi / 29.8 km)

What are the top vacation rentals in or near Jamestown?

The heart wants what it wants, and right now it wants to go on vacation. It's time to pack your bags and retreat to one of these top vacation rentals in or near Jamestown:

  • "Cabin - Private Catch And Release Lake" is popular with guests. Around 5 miles from Jamestown, it has 1 bedroom and plenty of useful amenities, including an iron and ironing board and a restaurant dining guide.
  • Another top choice is "Look - Out Lodge On Lake Cumberland", which is around 9 miles from Jamestown. Offering 5 bedrooms, outdoor furniture and a games room, it has everything you need to keep you content and comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Jamestown vacation rental for you.

Can I find log cabins to rent in or near Jamestown?

Pick a wonderful log cabin from the many scattered in or near Jamestown and you'll soon be inside your timber-clad hideaway, tasty tipple in hand, unwinding by a blazing fire. But adventure is right outside your door too. These cabins offer the perfect blend of fun and comfort:

  • "Lake Cumberland Custom Log Cabin Home On 32 Wooded Acres": This is an ideal base to try out some of the exciting outdoor activities this region has to offer, including snorkeling and water skiing.
  • "Rural Rustic Log Cabin At Lake Cumberland": Spend some time enjoying all the creature comforts at this log cabin. When it's time for some fresh air, horse riding and rafting are some awesome things to do.

What are the top-rated vacation rentals for weekend getaways in or near Jamestown?

If you've been busier than a squirrel in a nut factory, you deserve a break for a few days. Skip out of work early on Friday and live it up at one of these weekend getaways in or near Jamestown:

  • "Lake Cumberland Custom Log Cabin Home On 32 Wooded Acres" is ideal for a couple of days of enjoyment and rest. It comes with convenient amenities, such as an oven and a stovetop, and is located about 6 miles to the southeast of Jamestown.
  • Alternatively, throw a few clothes in a bag and enjoy a mini break at "New Fast Wifi Lake Cumberland Condo By Park Perfect Location Newly Updated". This great getaway is around 7 miles south of Jamestown and has water sports equipment and a smart TV.

Can I find studio apartments for rent in and around Jamestown?

Yes, you can. If you want a small but stylish stay, you can't go past a studio apartment. These compact properties ooze charm and are often conveniently placed in the heart of town. Check out the following options in or near Jamestown:

  • Escape on your own or take a few friends to "Cabin - Private Catch And Release Lake". You'll have loads of amenities to make your stay comfortable, including a fireplace and coffee and tea making facilities.
  • "Cabin - Private Catch And Release Lake - Boat Rental Included Close To Lake Cumberland" is another wonderful stay, offering all you need for a dream Jamestown escape. Useful amenities here include coffee and tea making facilities and a fridge.

Can I find short term rentals in or near Jamestown?

Whether you're chasing a cozy cottage or a house with room enough for the whole family, you'll find the perfect place on Vrbo. Enjoy some downtime at one of these getaways in or near Jamestown:

  • If you can only spare a couple of nights, "Brand New Cottage, Cozy Wooded Lot 2. 1 Miles From Beautiful Lake Cumberland" is a fantastic choice. It's close to central Jamestown, so you'll have easy access to all the top sights.
  • "Lake Cumberland Getaway, Just Minutes To Jamestown Marina" is also well located. Put your feet up here and find out why lots of guests rate this getaway highly.

What are the best romantic weekend getaways in or near Jamestown?

Forget chocolates and flowers. Sometimes all you need is to take off for the weekend, just you and your sweetheart. At Vrbo, we've got romantic getaways in and around Jamestown that would make even old Cupid green with envy. Here are some to tempt you:

  • Put on some relaxing tunes and chill together at "Cabin - Private Catch And Release Lake". Around 5 miles from Jamestown, this property has everything you could want for a romantic getaway, including a fireplace and a nearby marina.
  • Otherwise, spend a few blissful days canoodling and uncorking Champagne at "Look - Out Lodge On Lake Cumberland", around 9 miles from Jamestown. A fireplace and a dining table will help ramp up the romance.

What are the best large group vacation rentals in or near Jamestown?

Big groups mean enormous fun. They also mean finding a place that'll comfortably fit your whole gang. Browse our large group vacation rentals in or around Jamestown and get your favorite people together under the same roof:

  • A wealth of amenities including mountain views and a fireplace make "Look - Out Lodge On Lake Cumberland" a group favorite. This expansive property has 5 bedrooms and sleeps up to 12 people. From central Jamestown, it's around 9 miles away to the east.
  • Nothing is more important than spending time with the people you love, and "Lake Cumberland Custom Log Cabin Home On 32 Wooded Acres" makes it easy to do that. Located around 6 miles to the southeast of Jamestown, as many as 18 people can stay in this vacation rental which has 5 bedrooms. A kitchen and a water park are among the various amenities here.

What are the best houses for rent with a pool in or near Jamestown?

A pool is often a necessity when deciding where to stay on vacation, particularly if you're getting away with the kids. Check out these houses with a pool in or near Jamestown and spend your days splish-splashing around:

  • Treat your loved ones to a memorable break at "Lake House With Beautifull Lake Views Five Minutes To Jamestown Marina". There's a lot to love about this escape apart from its pool, such as a barbecue grill and outdoor furniture.
  • "Lake House Hideaway #3, Only 2 Miles From Jamestown Marina" is the type of place you go to get away from the everyday and enjoy your surroundings, starting with its pool. Free toiletries and a DVD player are also on hand to make your visit as comfy as possible.

Jamestown has a humid subtropical climate, with average summertime temperatures ranging from 65 ºF to 85 ºF. But there's no need to wait until summer to visit. Check out the search bar at the top of the page and adjust the filters to find the perfect Jamestown vacation rental and plan your escape for whatever season you like.

What are the best large family vacation rentals in or near Jamestown?

A family getaway should be all about spending quality time together and having new experiences. If you're looking for a home away from home that's big enough for all the gang, have a look at these large family vacation rentals in and around Jamestown:

  • Located approximately 9 miles to the east of Jamestown, "Look - Out Lodge On Lake Cumberland" fits up to 12 people over 5 bedrooms. As well as lots of space to sprawl out, amenities here include a microwave oven and a TV.
  • Another great home away from home is "Lake Cumberland Custom Log Cabin Home On 32 Wooded Acres". Around 6 miles southeast of Jamestown, it comes with 5 bedrooms, space for up to 18 guests, a TV and a dishwasher.

Can I find family cabin rentals in or near Jamestown?

Escape the daily grind and treat the people you love to a vacation of a different sort. Stay in one of these family cabin rentals in or near Jamestown and get the camping experience — but with all the creature comforts you're used to!

  • "Cabin - Private Catch And Release Lake" - This popular retreat offers a microwave oven and a fridge and is about 5 miles to the northwest of central Jamestown.
  • "Lake Cumberland Custom Log Cabin Home On 32 Wooded Acres" - This stay is another favorite with families and is around 6 miles southeast of Jamestown. Offering nearby birdwatching activities, childrens activities and more, it'll get your group's stamp of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Jamestown vacation rental that's perfect for your needs.