Holiday Rentals in Jamestown

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Holiday Rentals in Jamestown

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

10.0 out of 10, Exceptional, (184)
"It was a beautiful property and was very comfortable. "
The price is €287
includes taxes & fees
13 Oct - 14 Oct
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.

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

10.0 out of 10, Exceptional, (150)
"The house is beautiful, clean, and perfect for large groups. Suzanne was great to work with and very professional. Highly recommend her property and this beautiful home!"
The price is €530
includes taxes & fees
5 Oct - 6 Oct
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

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

10.0 out of 10, Exceptional, (24)
"Everything we needed for a fun, relaxing lake weekend! House was clean and fully stocked. The cute coffee bar, extra towels, and kids’ games were a bonus! The host was incredibly friendly and responsive. Room to park our 24’ boat and a 5 min drive to Jamestown marina. Highly recommend booking. "
The price is €342
includes taxes & fees
4 Oct - 5 Oct
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

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

9.4 out of 10, Exceptional, (3)
"Everything was great"
The price is €424
includes taxes & fees
5 Oct - 6 Oct
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

10.0 out of 10, Exceptional, (51)
"Great location and as advertised. "
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!

9.8 out of 10, Exceptional, (69)
"The property surrounding this cabin is lovely and the cabin itself was clean and comfortable. We would definitely recommend it for a family vacation."
Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!

Cumberland Get-A-Way located at entrance of State Park

10.0 out of 10, Exceptional, (19)
"We were just needing a quiet place where my son and I could fish and grieve the loss of my husband and this place gave us that! "
Cumberland Get-A-Way located at entrance of State Park

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

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

Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!

10.0 out of 10, Exceptional, (7)
"Was beautiful, clean and quiet"
The price is €320
includes taxes & fees
15 Oct - 16 Oct
Riverfront Cabin~Firepit~Private Boat Ramp w/ river access~Dog-Friendly!

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

9.8 out of 10, Exceptional, (30)
"We only stayed a short time but really enjoyed the pool and hot tub. The lake view and fire pit were a hit as well! "
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

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

9.6 out of 10, Exceptional, (231)
"This little house was just what we needed! It was far enough from town to have privacy and close enough to get anything we needed. We enjoyed the relaxing setting and the house was clean and had everything we needed!"
Lake Front Home with community boat ramp. Private, close to marinas and town.

This charming cozy cottage has a private hot tub, deck for fishing.

9.8 out of 10, Exceptional, (154)
"Great place. Very quite and peaceful. "
This charming cozy cottage has a private hot tub, deck for fishing.

Kozy Haven Log Cabin Rentals

3.0 star property
9.6 out of 10, Exceptional, (41)
"Very peaceful, quiet, and private and clean place to stay"
Kozy Haven Log Cabin Rentals

Little blue house on the lake

9.2 out of 10, Wonderful, (24)
"Loved our stay! Beautiful place. Just wish the lake access was better but due to the rain it was hard to make it down the steep hill. "
Little blue house on the lake

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

9.6 out of 10, Exceptional, (102)
"Great house and lost of fun things to do!"
4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

2 Bedroom lakeside to Dale Hollow Lake!

9.0 out of 10, Wonderful, (6)
"The cabins are right on the water perfect for fishing and boating. Our cabin was very nice and clean but our neighbors were complaining they did not have the same experience. Would definitely stay here again! "
2 Bedroom lakeside to Dale Hollow Lake!

Lakeside 3 bedroom chalet with hot tub!!

8.8 out of 10, Excellent, (6)
"Nice"
Lakeside 3 bedroom chalet with hot tub!!

Lake Cumberland custom log cabin home on 32 wooded acres

10.0 out of 10, Exceptional, (191)
"It was very beautiful and relaxing. Everything was so comfortable and inviting. "
Lake Cumberland custom log cabin home on 32 wooded acres

Perfect Lake House on Lake Cumberland

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

Cumberland River Cabin Rental

10.0 out of 10, Exceptional, (311)
"We had a great time! "
Cumberland River Cabin Rental
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

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, apart-hotels, 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 €287 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 Charming 5-bedroom/3-bath home with easy access to Lake Cumberland and Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!.

How many holiday rentals are there in Jamestown?

With 35 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.