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Featured Cottages in Jamestown

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

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

9.8 out of 10, Exceptional, (142)
"Was a great stay. Nice place, deck over a pond. Owner was great communication. highly recommend."
This charming cozy cottage has a private hot tub, deck for fishing.
Boating Mecca: Near Dale Hollow Lake & Golf!
Outdoor dining

Boating Mecca: Near Dale Hollow Lake & Golf!

10.0 out of 10, Exceptional, (68)
"Wonderful stay. Home is very clean and comfortable in an excellent location. Half way point between Dale Hollow marina and Mikes Landing. Host provided home baked cookies that were delicious. Many extras with towels and provided cookware. Property is beatifu south a peaceful back deck that's perfect for quiet relaxation. "
Boating Mecca: Near Dale Hollow Lake & Golf!
A true guest favorite! Super clean! Close to everything!
Terrace/patio

A true guest favorite! Super clean! Close to everything!

10.0 out of 10, Exceptional, (8)
"Rebecca went out of her way to make us feel comfortable. The house is clean and well stocked. Close to the lake. Perfect getaway!"
The price is AU$358
includes taxes & fees
30 Nov - 1 Dec
A true guest favorite! Super clean! Close to everything!
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
Property grounds

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

10.0 out of 10, Exceptional, (8)
"The property was very clean and a few minutes from Jamestown Marina. Plenty of parking for 2 trucks and a 40 ft. boat/trailer. We stayed for the poker run and had an amazing time."
The price is AU$621
includes taxes & fees
27 Nov - 28 Nov
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
Lake Front Home with community boat ramp. Private, close to marinas and town.
Interior

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

9.6 out of 10, Exceptional, (214)
"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...
Lake Front Home with community boat ramp. Private, close to marinas and town.
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Miscellaneous

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

10.0 out of 10, Exceptional, (31)
"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! "
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Marina

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

9.8 out of 10, Exceptional, (10)
"Cute--3 Bedroom/1 Bath stand alone building/cabin with hot tub--pet friendly! Clean + Had all the amenities needed for a weekend stay (or longer if need be). We had a great time by the firepit and using the hot tub. There was also cards and several board games to play. In a quiet neighborhood. Check in process was easy. Though located above the marina--was not walking distance --property does not overlook the lake or have steps leading down to the lake (unsure if there was a public access...
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Relaxing Lakefront Getaway Near Marina, Park, & Town
Outdoor dining

Relaxing Lakefront Getaway Near Marina, Park, & Town

10.0 out of 10, Exceptional, (142)
"My wife and I stayed for a weekend getaway. The property was great. There were many unlisted amenities. Do recommend. Maybe its intentional(bright evenings), but the limbs of the trees did obscure the lake view a bit. "
The price is AU$367
includes taxes & fees
9 Dec - 10 Dec
Relaxing Lakefront Getaway Near Marina, Park, & Town
Lake Cumberland Eclectic Retreat: Fire Pit + Views
Dining

Lake Cumberland Eclectic Retreat: Fire Pit + Views

10.0 out of 10, Exceptional, (13)
"This property was very beautiful, spacious, and clean. It was very comfortable for my family. The owner was very helpful and took care of any issues with great efficiency. "
Lake Cumberland Eclectic Retreat: Fire Pit + Views
Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!!
Exterior

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

10.0 out of 10, Exceptional, (19)
"Will definitely stay here again "
Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!!
Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!! -#2
Exterior

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

10.0 out of 10, Exceptional, (14)
"Cottage is right outside of Jamestown KY. You are close to lake Cumberland and also close to Jamestown. Cottage is beautiful and very spacious. Cottage comes with everything you could need during your stay. We will definitely be back! "
Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!! -#2
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
Smart TV

Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.

9.4 out of 10, Exceptional, (26)
"Clean & decor was nice, had everything we needed, warm house, easy checkin, tv was nice & kitchen was nice, location not far from town, need to clean up wood in back yard & work on driveways, favorite parts were lights on front deck (few bulbs need replaced)& bathroom tile in the shower was beautiful"
The price is AU$540
includes taxes & fees
1 Dec - 2 Dec
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
DHL Lake View Escape - 1 mi from Marina!
Fridge, microwave, oven, stovetop

DHL Lake View Escape - 1 mi from Marina!

10.0 out of 10, Exceptional, (14)
"Was very pleased with everything at this house. Grandkids loved the game room and we loved our space in livingroom. Very close to Wisdom Dock and we had a slip, made experience even better. I'll be back for sure!"
DHL Lake View Escape - 1 mi from Marina!
Dale Hollow Cottage w/ Covered Porch & Lake Views!
Fridge, microwave, stovetop, dishwasher

Dale Hollow Cottage w/ Covered Porch & Lake Views!

10.0 out of 10, Exceptional, (8)
"This house had everything we needed to enjoy our vacation at the lake. The important things for us on vacation is sleeping comfortably, a great view and the location close to the state park. We loved the back porch overlooking part of the lake and hills. The beds were very comfortable especially the king in the master. Great place to stay!"
Dale Hollow Cottage w/ Covered Porch & Lake Views!
Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp
Miscellaneous

Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp

10.0 out of 10, Exceptional, (5)
"We stayed here for a fishing tournament. The house was very clean and the hosts quickly communicated when we inquired about adding an additional night. We would definitely stay here again on future Lake Cumberland trips!"
Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp
Your idyllic getaway in the beautiful countryside of Somerset, Kentucky!
2 bedrooms, desk, iron/ironing board, free WiFi

Your idyllic getaway in the beautiful countryside of Somerset, Kentucky!

9.4 out of 10, Exceptional, (3)
"After booking this cottage for a family reunion weekend the check in process was sooo easy, the host gave us explicit instructions! We were delighted with the accommodation with only a few minor exceptions. First, the place was very tastefully decorated. The bedrooms were suited perfectly for guests, each having everything one could possibly need. The roomy kitchen had full sized appliances, including the coffee pot. The living room was a little bit cramped, but that allowed for easy...
Your idyllic getaway in the beautiful countryside of Somerset, Kentucky!
Restful Rustic Farmhouse on Lake Cumberland
Terrace/patio

Restful Rustic Farmhouse on Lake Cumberland

8.8 out of 10, Excellent, (5)
"We booked last minute and were suprised to find this availability. 9 adults and 3 children had plenty of room to spread out. We weren't there long enough to cook and enjoy all the house had to offer, so I can't comment on the amenities. Joe was gracious to let us check in a little early. Responsive to all msgs. Would definitely book again with the hope to stay longer next time!"
The price is AU$1,428
includes taxes & fees
27 Nov - 28 Nov
Restful Rustic Farmhouse on Lake Cumberland
Newly remodeled, handicap accessible overlooking pool , play area
Fridge, microwave, oven, stovetop

Newly remodeled, handicap accessible overlooking pool , play area

10.0 out of 10, Exceptional, (6)
"We just returned from a weekend stay. Property was just as described and location was perfect for our boating trip at Conley Bottom. Would stay here again!"
Newly remodeled, handicap accessible overlooking pool , play area
Everglow Hollow- Adorable Tiny House near Lake Cumberland, KY. Pet Friendly!
2 bedrooms, WiFi, bed sheets

Everglow Hollow- Adorable Tiny House near Lake Cumberland, KY. Pet Friendly!

9.6 out of 10, Exceptional, (4)
"The place was very unique, I have never seen a rental like this one. Overall, the communication was excellent. There was not much to nit pick other than the cleanliness of the property. Upon arrival there was a grill cover just laying on the front porch, and the outdoor patio set on the concrete slab had what appeared to be trash laying over it. There was a lot of dust in the home, especially on the fans and left over cereal from the last guests. It made me feel like I was responsible for...
Everglow Hollow- Adorable Tiny House near Lake Cumberland, KY. Pet Friendly!
Cumberland Lake House - 2 miles from Jamestown Marina - Sleeps 11
Exterior

Cumberland Lake House - 2 miles from Jamestown Marina - Sleeps 11

Cumberland Lake House - 2 miles from Jamestown Marina - Sleeps 11
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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Other property types in Jamestown

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
Property grounds

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

9.8 out of 10, Exceptional, (27)
"Great location. Great place, beautiful views"
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Miscellaneous

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

10.0 out of 10, Exceptional, (31)
"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! "
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Marina

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

9.8 out of 10, Exceptional, (10)
"Cute--3 Bedroom/1 Bath stand alone building/cabin with hot tub--pet friendly! Clean + Had all the amenities needed for a weekend stay (or longer if need be). We had a great time by the firepit and using the hot tub. There was also cards and several board games to play. In a quiet neighborhood. Check in process was easy. Though located above the marina--was not walking distance --property does not overlook the lake or have steps leading down to the lake (unsure if there was a public access...
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

What is there to do in Jamestown near my cottage?
The best travel accessory is a well-thought-out travel plan. Lake Cumberland State Resort Park is a terrific place to start your exploration of Jamestown.