Jamestown Holiday Rentals

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Our top choices for Jamestown holiday rentals

9.4 out of 10, Exceptional, (30 reviews)
"Great one night get away. Home was very clean and set up for all our needs. Tucked in the woods and very private. Little trick on getting the boat in and out but it all worked out. "
United States
Bobby E.
The price is NZ$665
includes taxes & fees
1 Mar - 2 Mar
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
10.0 out of 10, Exceptional, (196 reviews)
"Wonderful stay, great communication ans very peaceful. It had everything you could need for a relaxing get away, and plenty of space to do it. Will for sure stay again!!!!!"
United States
Lisa T.
The price is NZ$570
includes taxes & fees
1 Mar - 2 Mar
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.
10.0 out of 10, Exceptional, (161 reviews)
"Beautiful property with an amazing view"
United States
Michael P.
The price is NZ$1,039
includes taxes & fees
1 Mar - 2 Mar
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
9.2 out of 10, Wonderful, (14 reviews)
"Such a lovely property. Very cozy and inviting. We will definitely stay again."
United States
Jennifer S.
The price is NZ$587
includes taxes & fees
1 Mar - 2 Mar
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
10.0 out of 10, Exceptional, (6 reviews)
"This property is absolutely amazing so clean and easy to get to! "
United States
Bailee J.
The price is NZ$614
includes taxes & fees
2 Mar - 3 Mar
New Rustic Home Near State Dock
9.4 out of 10, Exceptional, (10 reviews)
"Great place "
United States
Melissa B.
The price is NZ$640
includes taxes & fees
1 Mar - 2 Mar
Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!
9.6 out of 10, Exceptional, (11 reviews)
"Our family had an amazing time at this vacation home! We had excellent communication with the owners and the place had everything we needed! Will definitely stay here again! Thank you for a wonderful holiday weekend!"
United States
Dana C.
The price is NZ$1,024
includes taxes & fees
3 Mar - 4 Mar
Restful Rustic Farmhouse on Lake Cumberland
10.0 out of 10, Exceptional, (19 reviews)
"Amazing stay! House is very clean with lovely decor! Will stay here again for sure!!"
United States
Jennifer L.
The price is NZ$641
includes taxes & fees
9 Mar - 10 Mar
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Apartment in Jamestown

New Near Jamestown Dock - A
9.8 out of 10, Exceptional, (22 reviews)
"Great stay"
United States
Rob W.
The price is NZ$340
includes taxes & fees
11 Mar - 12 Mar
New Near Jamestown Dock - A
10.0 out of 10, Exceptional, (9 reviews)
"Very clean and all amenities set up perfectly for our stay. Made a perfect middle ground for visiting mammoth caves and cumberland falls."
United States
Brice L.
The price is NZ$395
includes taxes & fees
9 Mar - 10 Mar
Guest Favorite! Super Clean! Close to Everything!
10.0 out of 10, Exceptional, (5 reviews)
"The stay was very nice and peaceful "
United States
earl c.
The price is NZ$696
includes taxes & fees
11 Mar - 12 Mar
Hot Tub & Firepit~Game Center~Lake Cumberland~Family Friendly~River Boat Ramp
9.0 out of 10, Wonderful, (8 reviews)
"Great location."
United States
Donald S.
The price is NZ$239
includes taxes & fees
1 Mar - 2 Mar
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
10.0 out of 10, Exceptional, (10 reviews)
"Great location, house is very nice, clean and spacious and close to the Jamestown boat ramp. Will definitely stay here again."
United States
Michael o.
The price is NZ$822
includes taxes & fees
1 Mar - 2 Mar
Great place to gather near Lake Cumberland
10.0 out of 10, Exceptional, (3 reviews)
"Nice place with boat ramp."
United States
Josh S.
The price is NZ$637
includes taxes & fees
1 Mar - 2 Mar
Cabin w/ Firepit~Pickleball~Arcade Games~River Boat Ramp~20 Min Lake Cumberland
10.0 out of 10, Exceptional, (4 reviews)
"The host was very welcoming, check-in and out was super easy. This was the most stocked VRBO I have ever visited, taking into account even the small things in the bathroom. "
United States
Elyce E.
The price is NZ$604
includes taxes & fees
11 Mar - 12 Mar
HOT TUB~Dog Friendly Cabin~Fishing~River boat ramp~20 Min to Lake Cumberland
10.0 out of 10, Exceptional, (4 reviews)
"Yes the hot tub was great and very pet friendly. We loved the amenities! What a great stay. We will be back!! "
United States
Marina W.
The price is NZ$635
includes taxes & fees
9 Mar - 10 Mar
Cabin w/ River Boat Ramp~Private HotTub~Sauna~Lake Cumberland~Firepit~Pickleball
10.0 out of 10, Exceptional, (2 reviews)
"Was perfect! Would absolutely stay again !"
United States
marsha w.
The price is NZ$671
includes taxes & fees
11 Mar - 12 Mar
Fishing~HotTub&Sauna~Pickleball~PingPong~Lake Cumberland~Playground~Firepit
9.6 out of 10, Exceptional, (4 reviews)
"This house was beautiful and perfect for what we needed. "
United States
Shavona M.
The price is NZ$732
includes taxes & fees
17 Mar - 18 Mar
Lake Cumberland Cabin - Spa, Firepit, Scenic Views
9.0 out of 10, Wonderful, (2 reviews)
The price is NZ$671
includes taxes & fees
11 Mar - 12 Mar
Hot Tub~River Boat Ramp~Pickleball~Lake Cumberland~Family Friendly Cabin
10.0 out of 10, Exceptional, (1 review)
"Th place was extremely clean, check in was simple and easy, the listing was exactly as described. The sheets on the bed were amazing and the beds were comfortable "
United States
Dillon R.
The price is NZ$286
includes taxes & fees
1 Mar - 2 Mar
The Lodge Lake Retreat – Family-Friendly with Private River Access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Jamestown Hotel Reviews

Find out more about Jamestown

Everything you need to know about Jamestown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jamestown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jamestown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Jamestown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jamestown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jamestown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jamestown holiday rentals we have selected for you start as low as NZ$267 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jamestown rentals

At Expedia, we put the best Jamestown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jamestown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jamestown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jamestown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Jamestown?

Yes, there are holiday rentals close to the most popular sights in Jamestown, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Jamestown speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the waterfront and parks during your trip.

What are some of the best holiday rentals that Jamestown has to offer?

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.: This highly rated holiday home rental in Jamestown is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Another good choice for your trip to Jamestown is Charming 5-bedroom/3-bath home with easy access to Lake Cumberland.

How many holiday rentals are there in Jamestown?

With 34 Expedia holiday rentals, you're guaranteed to find just the right place for your Jamestown stay.

What’s there to see and do in Jamestown?

Lake Cumberland State Resort Park and Wolf Creek National Fish Hatchery are a couple of lovely local spots to get outside and enjoy nature. While here, Cumberland River and Jamestown Marina are other places worth a visit.

What’s a holiday rental in Jamestown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Jamestown. Holiday rentals provide amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.