Jamestown Holiday Rentals

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Holiday Rentals in Jamestown

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

Jamestown
10.0 out of 10, Exceptional, (153)
"Check in was very easy, beautiful home,views were pretty,overall great family time!"
United States
paige m.
The price is NZ$934
includes taxes & fees
12 Nov - 13 Nov
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.

Jamestown
10.0 out of 10, Exceptional, (192)
"Overall we had a nice stay here. The extra driveway made it easy to park our boat which was a big reason for picking this property. The road is a bit narrow, so go slow. "
United States
Ben M.
The price is NZ$571
includes taxes & fees
25 Nov - 26 Nov
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.

Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Jamestown
10.0 out of 10, Exceptional, (19)
"Amazing stay! House is very clean with lovely decor! Will stay here again for sure!!"
United States
Jennifer L.
The price is NZ$697
includes taxes & fees
23 Nov - 24 Nov
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Gorgeous 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #409!

Jamestown
10.0 out of 10, Exceptional, (2)
Gorgeous 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #409!

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Jamestown
9.8 out of 10, Exceptional, (26)
"The property was great! Unfortunately, we had to leave early for a family emergency after the first day. But the property manager made it easy for everything from the time we checked in. We will use them again if the property is available for our next visit. "
United States
Kevin W.
The price is NZ$694
includes taxes & fees
13 Nov - 14 Nov
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

Jamestown
10.0 out of 10, Exceptional, (13)
"Great experience, very cute home. Would love to visit again! "
United States
Adam F.
The price is NZ$779
includes taxes & fees
12 Nov - 13 Nov
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

Apple Valley Comfy “Treehouse" 2-Bedroom Condo inside Lake Cumberland State Park

4.0 star property
Jamestown
9.8 out of 10, Exceptional, (64)
"We had a wonderful time! Beautiful condo! "
United States
Shannon K.
Apple Valley Comfy “Treehouse" 2-Bedroom Condo inside Lake Cumberland State Park

Charming 5-bedroom/3-bath home with easy access to Lake Cumberland

Jamestown
9.6 out of 10, Exceptional, (5)
"Jenn was super responsive and gave us plenty of info on fishing/boating access in the area. The house was a great size with a cute unique layout. Huge deck for plenty of outside hang time and close to a boat ramp to easily drop my canoe in. Just a few minutes from the State Park too! "
United States
Joe P.
The price is NZ$858
includes taxes & fees
15 Nov - 16 Nov
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland

NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

Jamestown
10.0 out of 10, Exceptional, (53)
"Beautiful home with a beautiful view! Quick responses from the owner and we can’t wait to come back next year!"
United States
Kyle B.
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!

Jamestown
9.8 out of 10, Exceptional, (70)
"All things were very enjoyable and the place is lovely"
United States
Bradford B.
Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!

Cozy 3 Bed Log Cabin at Jamestown Marina, Tucked Away in a Wooded Area #301

Jamestown
7.8 out of 10, Good, (6)
"The excessive humidity and musty odor were the overarching issues. It made our stay an unpleasant experience. Additionally, there is torn carpet front and center when you walk in just beyond a very dirty front door. The unit needs a dedicated portable dehumidifier and attention to detail on numerous items/issues."
United States
Anonymous traveller
Cozy 3 Bed Log Cabin at Jamestown Marina, Tucked Away in a Wooded Area #301

6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

Monticello
9.8 out of 10, Exceptional, (32)
"Perfect accommodation for our family group ages 2 to 85. Wonderful and relaxing week. Thank you!"
United States
Nancy L.
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

Lakeside 3 bedroom chalet with hot tub!!

Byrdstown
9.0 out of 10, Wonderful, (8)
"We had the best time. Cabin was very nice. Everything was close for the kids. We would definitely go back. The only downfall was the mattresses. They were horrible and caved in the middle. None of us got a good nights rest. And nobody could connect to wifi, even with the password it would continue to spin and never connect. Other than that, we enjoyed our stay very much "
United States
Tammy M.
Lakeside 3 bedroom chalet with hot tub!!

Kozy Haven Log Cabin Rentals

3.0 star property
Columbia
9.6 out of 10, Exceptional, (42)
"Small cozy cabin. Very clean. Only here overnight. Dog is happy, friendly precocious cat hanging around."
United States
Melissa
The price is NZ$284
includes taxes & fees
12 Dec - 13 Dec
Kozy Haven Log Cabin Rentals

Cumberland River Cabin Rental

Burkesville
10.0 out of 10, Exceptional, (318)
"Great place and location "
United States
Anonymous traveller
Cumberland River Cabin Rental

Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

Monticello
9.8 out of 10, Exceptional, (63)
"Great spot close to lake cumberland and conley botom marina"
United States
Michael W.
Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

Monticello
9.6 out of 10, Exceptional, (106)
"We enjoyed our stay at the property. The pool and hot tub were wonderful!"
United States
Jenny M.
4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

Lake Front Home with community boat ramp. Private, close to marinas and town.

Somerset
9.6 out of 10, Exceptional, (236)
"Loved everything about our stay. The cabin was awesome, the hosts are fantastic and we plan to come back. "
United States
Kim W.
Lake Front Home with community boat ramp. Private, close to marinas and town.

Lakeside 3 Bedroom Chalet with a hot tub!

Byrdstown
9.0 out of 10, Wonderful, (6)
"Amazing stay, very nice hosts. Would stay again!!"
United States
Nicholas
Lakeside 3 Bedroom Chalet with a hot tub!

Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings

Nancy
9.6 out of 10, Exceptional, (183)
"We loved our stay at this property! Nice location, quiet, relaxing, pretty views, everything there that we needed, and great memories made. Definitely recommend this rental!"
United States
Kara K.
Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings
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$284 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. Some other top choices in Jamestown are Luxe Lake Cumberland Retreat w/ Decks on 1 Acre! and Charming 5-bedroom/3-bath home with easy access to Lake Cumberland.

How many holiday rentals are there in Jamestown?

With 37 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, Jamestown Marina and Cumberland River 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.