Jamestown Holiday Rentals

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Holiday Rentals in Jamestown

Exterior
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
10.0 out of 10, Exceptional, (5)
"Property owner was very helpful, cabin was clean and had everything we needed. Great location!"
The price is NZ$727
includes taxes & fees
15 May - 16 May
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Outdoor dining
Ultimate Getaway Lake Cumberland, Great Location, easy access to water
9.2 out of 10, Wonderful, (134)
"2 night stay. Friday and Saturday nights. Clean comfortable home. Strong wi-fi. Most everything needed was supplied, towels, linen, pots, pans, etc. bed was firm and comfortable. lake access was close but the water water level was very low at the time of our visit. Neighbors that we met, were hospitable if not friendly. Only room in driveway for a very small boat trailer and truck. Overall very happy with our stay. Hope to return next year."
Ultimate Getaway Lake Cumberland, Great Location, easy access to water
View from property
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
10.0 out of 10, Exceptional, (7)
"The house is beautiful, has everything you would need, easy process and the view is amazing. A great place for a relaxing weekend!"
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
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Terrace/patio
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
9.8 out of 10, Exceptional, (18)
"Great place to stay"
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
Property grounds
Harbor Hilltop at Cumberland
10.0 out of 10, Exceptional, (3)
"This was a new area for us. It was a very nice location."
The price is NZ$621
includes taxes & fees
29 May - 30 May
Harbor Hilltop at Cumberland
Property grounds
Large Lake Cumberland Retreat w/ Deck Views!
8.6 out of 10, Excellent, (7)
"Shared this house with four other co workers and we each had plenty of space. Everything is well equipped and clean."
Large Lake Cumberland Retreat w/ Deck Views!
Smart TV, fireplace
Luxury Cottage with pool 2.1 miles from beautiful Lake Cumberland -#2
10.0 out of 10, Exceptional, (10)
"Lily Creek is absolutely beautiful. Deana goes way above and beyond anything I have experienced with vrbo rentals. The home was clean, the kitchen had everything we needed, and the living spaces were comfortable and spacious. It is minutes away from Jamestown Marina, which is perfect for easy ramp access. We absolutely hope to return next summer!"
Luxury Cottage with pool 2.1 miles from beautiful Lake Cumberland -#2
Exterior
Secluded Jamestown Cabin w/ Fire Pit!
Secluded Jamestown Cabin w/ Fire Pit!
Property grounds
New cabin sleeps 6 only 3mi from Jamestown Dock + Outdoor fun!
10.0 out of 10, Exceptional, (8)
"Absolutely loved staying here. My husband and I stayed here with our two children and dog. We told the host we were celebrating a birthday and when we arrived there was a birthday balloon and freshly baked cookies. The host was very friendly and it felt like we were staying with family. Brian was so kind to our children. They set up the volleyball and soccer nets and had everything we needed for outdoor fun. Also gave us tips for local places to shop, eat, and have fun. I would definitely...
The price is NZ$331
includes taxes & fees
15 May - 16 May
New cabin sleeps 6 only 3mi from Jamestown Dock + Outdoor fun!
Private kitchen
Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!
9.8 out of 10, Exceptional, (55)
"The driveway and the house was really nice ! Had enough room to turn your boat around . The area was very quiet and relaxing . The home was decorated nicely . The walk way going in the back of the house did have some loose boards on path . We enjoyed our stay . Wish there were more restaurants in the area of the town but we made do . Our next trip back will be when the marina is in season though . Cause when we were there everything was closed , but we did enjoy putting our fishing boat in the...
Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!
Smart TV, fireplace
Luxury Cottage with pool, 2.1 miles from beautiful Lake Cumberland
10.0 out of 10, Exceptional, (10)
"Great set up for larger group!"
Luxury Cottage with pool, 2.1 miles from beautiful Lake Cumberland
Dining
Lake Front Home with community boat ramp. Private, close to marinas and town.
9.6 out of 10, Exceptional, (198)
"My husband & I stayed at this beautiful house for a week for our anniversary and it was absolutely wonderful! The view was beautiful and the house was spotless. Comfy furniture to relax after our days of sightseeing. The ride to the house was all paved and easy to maneuver, especially for us Floridians! Linda is awesome and communicated excellently. We went to Cumberland Falls (amazing!) and also the Cave Hill Winery among many other historical sites. Most were less than 30 min away. Lots to do...
Lake Front Home with community boat ramp. Private, close to marinas and town.
Cabin 2 Angler's Paradise | Living area
Kozy Haven Log Cabin Rentals
3.0 star property
9.4 out of 10, Exceptional, (14)
"All set up and ready to go! Clean and comfy. Second time we have stayed and love it!"
The price is NZ$223
includes taxes & fees
15 May - 16 May
Kozy Haven Log Cabin Rentals
Property grounds
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
10.0 out of 10, Exceptional, (86)
"The location was quiet and like the listing states."
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Property grounds
Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings
9.6 out of 10, Exceptional, (162)
"My family stayed for a long weekend and enjoyed the comfortable setup of this very clean home. The description matches the website and the cabin decor is adorable. The owners stocked the cabin well. We had a partial lake view even with the trees!"
Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings
Exterior
Private Catch And Release Lake--Boat Rental Included! Close to Lake Cumberland!
10.0 out of 10, Exceptional, (217)
"Very well maintained grounds and the cabin was comfortable. Peace and quiet for the most part as can be expected on a farm. The hosts were attentive and provided everything you could ask for. As the title entails, 2 dozen duck were always around but, not a nuisance. Watching large catfish, bass, bluegill and turtles in the pond was nice."
Private Catch And Release Lake--Boat Rental Included! Close to Lake Cumberland!
Terrace/patio
Boating Mecca: Near Dale Hollow Lake & Golf!
10.0 out of 10, Exceptional, (57)
"property was stellar and owners went above and beyond on every level"
Boating Mecca: Near Dale Hollow Lake & Golf!
Property grounds
Lake House near Green River Lake and minutes from several marinas.
9.2 out of 10, Wonderful, (73)
"Great place for a father and son hunting trip! Perfectly located near tons of public hunting land and lake access! The deck and fire pit were our nightly reminiscing spot and perfect for star gazing and quiet! The house has all you could ask for for a perfect family getaway! Hope to be back soon!"
Lake House near Green River Lake and minutes from several marinas.
Fridge, microwave, oven, stovetop
Million Dollar View! Large Lakehouse Over-Looking Lee's Ford Marina
9.8 out of 10, Exceptional, (81)
"Great property and beautiful view! Bedrooms are on 3 different levels so privacy was perfect for all. Hope to be back!"
The price is NZ$1,183
includes taxes & fees
15 May - 16 May
Million Dollar View! Large Lakehouse Over-Looking Lee's Ford Marina
Exterior
Perfect Lake House on Lake Cumberland
10.0 out of 10, Exceptional, (1)
"The home was exactly as pictured online. It was immaculately clean and owner was very responsive, even reaching out to us to simply make sure we were comfortable. There are areas to be together as a large group in the house and the layout also provides plenty of privacy with 8 separate bedrooms. We had an amazing stay and will definitely stay here again next year."
Perfect Lake House on Lake Cumberland
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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.

Other types of properties in Jamestown you may be interested in

Lobby lounge
Lake Cumberland State Resort Park
3.0 star property
8.8 out of 10, Excellent, (390)
"The trail near the lodge needs to be marked. The trail map showed that paths we could not find. Dinner was good and quite reasonably priced. "
The price is NZ$174
includes taxes & fees
15 May - 16 May
Lake Cumberland State Resort Park
View from property
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
10.0 out of 10, Exceptional, (7)
"The house is beautiful, has everything you would need, easy process and the view is amazing. A great place for a relaxing weekend!"
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Exterior
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
10.0 out of 10, Exceptional, (5)
"Property owner was very helpful, cabin was clean and had everything we needed. Great location!"
The price is NZ$727
includes taxes & fees
15 May - 16 May
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Jamestown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Jamestown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Jamestown. Seeing all the best attractions is bound to make you fall in love with Jamestown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Jamestown short-term rentals, that won’t be hard to do.

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.

How many holiday rentals are there in Jamestown?

With 28 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 Cumberland River are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Wolf Creek National Fish Hatchery and Lindsey Wilson College.

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.

Recent reviews of Jamestown properties
Expedia verified reviews