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Jamestown Holiday Rentals

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Holiday Rentals in Jamestown

Holiday Home in Jamestown

10.0 out of 10, Exceptional, (155)
"Check in was very easy, beautiful home,views were pretty,overall great family time!"
United States
paige m.
The price is AU$884
includes taxes & fees
23 Dec - 24 Dec
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

Cottage in Jamestown

9.8 out of 10, Exceptional, (26)
"The house was great! Clean, convenient and very quiet. We would definitely stay again!! "
United States
Toby E.
The price is AU$596
includes taxes & fees
13 Dec - 14 Dec
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Cottage in Jamestown

10.0 out of 10, Exceptional, (13)
"Great place to stay by the lake!"
United States
Grant B.
The price is AU$670
includes taxes & fees
7 Dec - 8 Dec
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

Condo in Jamestown

4.0 star property
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

Holiday Home in Jamestown

10.0 out of 10, Exceptional, (19)
"Thanks Landon we had a great stay and the house was great!!! "
United States
Sally J.
Cumberland Get-A-Way located at entrance of State Park

Cabin in Jamestown

10.0 out of 10, Exceptional, (2)
"5 stars!"
United States
Lisa W.
The price is AU$549
includes taxes & fees
6 Jan - 7 Jan 2026
HOT TUB~Dog Friendly Cabin~Fishing~River boat ramp~20 Min to Lake Cumberland

Cottage in Jamestown

10.0 out of 10, Exceptional, (193)
"Overall the property was nice and in a good location. James town marina only a few minutes away. "
United States
David E.
The price is AU$527
includes taxes & fees
14 Dec - 15 Dec
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.

Holiday Home in 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 AU$737
includes taxes & fees
8 Dec - 9 Dec
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland

Cottage in Jamestown

10.0 out of 10, Exceptional, (53)
"Great location and as advertised. "
United States
Mike G.
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

Holiday Home in 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 AU$596
includes taxes & fees
12 Dec - 13 Dec
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Cabin in Jamestown

2.0 star property
9.4 out of 10, Exceptional, (13)
"This is a beautiful place to stay with tons of amenities. We loved the cabin I do wish it was a different location though but they really can’t help that! We had a great experience and I hope to return one day."
United States
Olivia L.
The price is AU$540
includes taxes & fees
7 Dec - 8 Dec
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build

Cabin in Jamestown

7.8 out of 10, Good, (9)
"This cabin is cozy and comfortable. Very clean. The kids loved the loft area where they slept and it's close to everything in Jamestown. "
United States
Nick B.
3 Bed Log Cabin Located 0.5 miles from Safe Harbor Jamestown #302

Cabin in Byrdstown

9.0 out of 10, Wonderful, (8)
"Nice"
United States
William B.
Lakeside 3 bedroom chalet with hot tub!!

Holiday Home in Monticello

9.8 out of 10, Exceptional, (33)
"Perfect for a large family. The house and pool are great and the view is amazing! "
United States
MARY BETH K.
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

Holiday Home in Monticello

9.8 out of 10, Exceptional, (64)
"Good place to stay. Plenty of space for our family. Property is managed well. Pool was superb. Location great for boating activity on the Cumberland River/Lake."
United States
Sharon D.
Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

Holiday Home in Somerset

10.0 out of 10, Exceptional, (11)
"Great property, close to everything. Would stay again "
United States
Stephen B.
Perfect Lake House on Lake Cumberland

Holiday Home in Somerset

10.0 out of 10, Exceptional, (15)
"It was a wonderful stay. Beautiful view!"
United States
Vanessa C.
The price is AU$677
includes taxes & fees
16 Dec - 17 Dec
Joy On The Lake · Cumberland Canvas: Lake View, Fire Pit & Game Room

Cabin in Byrdstown

6.0 out of 10, (1)
"Cabin was outdated and really not made for 12 people. Not enough space in living room or kitchen. Enjoyed the view. "
United States
Diana P.
Beautiful 6 Bedroom Cabin with Hot Tub and a Lakeview of Dale Hollow Lake #12

Cabin in Burkesville

10.0 out of 10, Exceptional, (320)
"Great place and location "
United States
Anonymous traveller
Cumberland River Cabin Rental

Cottage in Somerset

9.6 out of 10, Exceptional, (238)
"Beautiful place "
United States
Roy W.
Lake Front Home with community boat ramp. Private, close to marinas and town.
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 favourite 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 depend 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 AU$527 per night. Entering your travel dates in the search wizard might find you 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, 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.