Jamestown Holiday Rentals : Search Short-Term Rentals

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

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre! : This highly rated holiday home rental in Jamestown is located on a lake, and has a fireplace, a furnished patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Another good choice for your trip to Jamestown is Charming 5-bedroom/3-bath home with easy walk to private slip on Lake Cumberland .

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Holiday Rentals in Jamestown

"I can’t stress enough how BEAUTIFUL the view is from both inside(huge windows) and outside(2 levels of deck viewing & seating)! Wonderfully decorated, and super comfy furnishings. Definitely recommend, and will be back! "

"The property was excellent and the family had a great time "

"The location was very convenient to the State Park Marina. The area was very pretty and felt secluded. Some of us took advantage of the fishing pond. We had a group of 19 and there was plenty of room for all. The only issue we had was the hot tub was not functioning, It would have been nice, but did not take away from our enjoyment of our weekend. We would definitely stay here again!"

"Enjoyed and was not disappointed."

"House has everything you need. It’s close distance to the marina. We enjoyed our stay."

includes taxes & fees

10 Feb - 11 Feb

"Will definitely stay here again "

"We enjoyed our stay. The scenery was amazing. The cabin was clean. The only problem was that there was no stopper for the sink or a scrubber sponge to wash dishes. "

"I would have given 10 stars if possible. This cabin is fully stocked with anything and everything you need. Just pack clothes, stop for groceries as not much close by to grab a meal. Perfect for family or couples. Grounds are very family friendly. Highly recommend this cabin or any other offered by Cabins on the Cumberland."

"Good stay ! Closer to the highway .. 🤗 "

includes taxes & fees

10 Feb - 11 Feb

"My family of nine and I had a great time and plenty of room. The views are incredible. The toys including pool table and foosball were used heavily. The hot tub was very comfortable and easy to use. There were a couple of unexpected bonuses including an extra refrigerator in the garage which was very helpful for all the food we needed for Thanksgiving, and secondly that they had two sets of washers and dryers which was very helpful for a large group. The second flat parking pad beyond the pool...

"Our third year at this location for our family and friends get together. Great location. Perfect for our event! Thanks to the host for all the preparations. Highly satisfied and will very likely use the same property again next year. "

"We all had a great time celebrating our Mom, (Grandma, Great Grandma's) 92 Birthday. Kids had a great time playing all the fun "toys" available on the 1st Floor- overall a really great time. "

"Everything was great.Very clean!Love that there wasnt a cleaning fee unless we didnt clean up before leaving!"

"We enjoyed our stay at this cute cabin with a great view located close to town. The hosts were excellent at communication and responded quickly. The deck is the focal point and is great for sitting out and admiring the water, enjoying an evening fire or cooking out dinner. My only complaint is in sleeping comfort. The bed in the main bedroom was so hard the first night that we switched to the other bedroom the second night. In that room, the bed was much better, but the window blind is too small...

"This is the best VRBO that we've stayed in. The fresh baked cookies when we walked in the door. The cleanliness was excellent. The home was well decorated, and the master bed was incredible. Highly recommend. We will be booking with them next time."

includes taxes & fees

10 Feb - 11 Feb

"We enjoyed our stay. The house was beautiful and well equipped. Enjoyed the pool table and air hockey downstairs. We would definitely stay again!!"

"The home is absolutely stunning and the pictures do not do it justice! Own"

includes taxes & fees

10 Feb - 11 Feb

"We had an amazing stay at the property. The house was very clean and had tons of amenities! Beds were very comfortable, kitchen was stocked with complimentary chips and had fresh flowers out. We loved the sunroom and spent a ton of time out there watching Tv, watching movies, and playing PlayStation. Internet was non-existent the last couple days but we knew from the listing that it was hit or miss and we used our hotspots. Will definitely be traveling here again to stay in the future!"

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Other types of properties in Jamestown you may be interested in

"A beautiful place to get away "

includes taxes & fees

12 Feb - 13 Feb

"This home is spacious, clean and beautiful. The bathrooms are large, with luxurious showers. The kitchen is also large and it was perfect for prepping dinner for our large family. We all enjoyed the big, open game/rec room! Our host was extremely helpful and went above and beyond to accommodate us! I highly recommend this property!"

"I can’t stress enough how BEAUTIFUL the view is from both inside(huge windows) and outside(2 levels of deck viewing & seating)! Wonderfully decorated, and super comfy furnishings. Definitely recommend, and will be back! "

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 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.

Recent reviews of Jamestown properties

5/5 Excellent

"Lady at the front dexk qas great!!"

A verified traveller from Winamac stayed at Sleep Inn & Suites

Posted 5 days ago

5/5 Excellent

Youve got to try this place PERFECT

"You have to try this place if you're ever near there. The staff everyone is awesong. Our waiter at the restawhat's the best. We can't remember his name. But I know his first name started with the W you have a Marina you have a bar. You have a restaurant. They have an outside pool and inside pull table ping pong table. And? They have a little store also in the park!! They have made this an actual resort. You don't have to leave the park. Anything you need is right there. None of the rooms are with the lodge. Because I know some people don't want the staff right there underneath them. It's room and the section we had had balconies that showed a view of the lake. You can rent boats, you can rent skis. You can rent jetski's absolutely awesome if you ever round there and you got the money tried out and it's not expensive at all. The staff are great. You need anything that got you probably one of the best places I've been in a long, long time. It is absolutely beautiful! Also beware.There is animals around and they're used to people. Nothing attacked us or anything like that bur the deer will walk right up to you i wouldn't recommend trying to pet them because you never know how their going to react! "

A verified traveller stayed at Lake Cumberland State Resort Park

Posted 2 months ago

Luxury Farmhouse with pool, 2 miles from Jamestown Marina!!

5/5 Excellent

Upscale Farmhouse

"This home is spacious, clean and beautiful. The bathrooms are large, with luxurious showers. The kitchen is also large and it was perfect for prepping dinner for our large family. We all enjoyed the big, open game/rec room! Our host was extremely helpful and went above and beyond to accommodate us! I highly recommend this property!"

A verified traveller stayed at Luxury Farmhouse with pool, 2 miles from Jamestown Marina!!

Posted 2 months ago

3 Bed Log Cabin Located 0.5 miles from Safe Harbor Jamestown #302

5/5 Excellent

Beautiful scenery

"We enjoyed our stay. The scenery was amazing. The cabin was clean. The only problem was that there was no stopper for the sink or a scrubber sponge to wash dishes. "

A verified traveller stayed at 3 Bed Log Cabin Located 0.5 miles from Safe Harbor Jamestown #302

Posted 3 months ago

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

5/5 Excellent

Family Weekend Getaway

"I can’t stress enough how BEAUTIFUL the view is from both inside(huge windows) and outside(2 levels of deck viewing & seating)! Wonderfully decorated, and super comfy furnishings. Definitely recommend, and will be back! "

A verified traveller stayed at NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

Posted 4 months ago

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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?

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!: This highly rated holiday home rental in Jamestown is located on a lake, and has a fireplace, a furnished patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Another good choice for your trip to Jamestown is Charming 5-bedroom/3-bath home with easy walk to private slip on 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.

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Jamestown Holiday Rentals

Plan, book, stay with confidence

Check prices for these dates

Holiday Rentals in Jamestown

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

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

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

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

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

Charming 5-bedroom/3-bath home with easy walk to private slip on Lake Cumberland

Charming 5-bedroom/3-bath home with easy walk to private slip on Lake Cumberland

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

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

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

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

Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!!

Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!!

3 Bed Log Cabin Located 0.5 miles from Safe Harbor Jamestown #302

3 Bed Log Cabin Located 0.5 miles from Safe Harbor Jamestown #302

NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build

NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build

Riverfront Cabin~Sleeps 18~Private River Boat Ramp~20 Min drive Lake Cumberland

Riverfront Cabin~Sleeps 18~Private River Boat Ramp~20 Min drive Lake Cumberland

Kozy Haven Log Cabin Rentals

Kozy Haven Log Cabin Rentals

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

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

Lake house with boat ramp access across the street & tons of boat parking space.

Lake house with boat ramp access across the street & tons of boat parking space.

Cumberland Belle Lakehouse 9 bedrm, 20 bed, 7 bath, swimspa/hotub&sauna

Cumberland Belle Lakehouse 9 bedrm, 20 bed, 7 bath, swimspa/hotub&sauna

Cumberland River Cabin Rental

Cumberland River Cabin Rental

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

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

Boating Mecca: Near Dale Hollow Lake & Golf!

Boating Mecca: Near Dale Hollow Lake & Golf!

Perfect Lake House on Lake Cumberland

Perfect Lake House on Lake Cumberland

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

Little blue house on the lake

Little blue house on the lake

Other types of properties in Jamestown you may be interested in

Lake Cumberland State Resort Park

Lake Cumberland State Resort Park

Luxury Farmhouse with pool, 2 miles from Jamestown Marina!!

Luxury Farmhouse with pool, 2 miles from Jamestown Marina!!

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

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

Find out more about Jamestown

Find out more about Jamestown

Recent reviews of Jamestown properties

Recent reviews of Jamestown properties

Sleep Inn & Suites

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Frequently asked questions