Jamestown, KY Cottages from SAR 904

Q: Why book your cottage in Jamestown with Expedia?

We think that a vacay should be a piece of cake, so if you're chasing cottages in Jamestown at an affordable price, Expedia has got your back. Stick to the budget and opt for a wallet-friendly option far from the rush of the city, or splurge on a 5-star cottage to spoil your loved ones.

Q: How can I find cheap cottages in Jamestown?

Expedia is here to help you locate cheap cottages in Jamestown. To book a superb stay in a matter of clicks, simply use our convenient filter tool to refine your search by star rating, amenities and budget.

An aerial view of a coastal area with a lighthouse, a parking lot, and a rocky shoreline.

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Our top choices for Jamestown cottages

A wooden deck with a table and chairs, surrounded by a wooden railing and a view of a forested area.

1. 4BR Charming Cabin Retreat | Hot Tub, Fire Pit

Jamestown

Shavona M.

SAR 1,586 total

includes taxes & fees

20 Oct - 21 Oct

A covered porch with a blue exterior, a bright green door, and a seating area with a sofa and two side tables.

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

Jamestown

Emily W.

SAR 1,539 total

includes taxes & fees

27 Oct - 28 Oct

A single-story house with a covered porch, a small deck, and a front yard.

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

Jamestown

Amber R.

SAR 1,887 total

includes taxes & fees

18 Oct - 19 Oct

A cabin surrounded by dense forest, with a gravel path leading to it.

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

Jamestown

Lena R.

SAR 1,887 total

includes taxes & fees

27 Oct - 28 Oct

A large, two-story house with a wrap-around porch, surrounded by lush green trees.

5. Restful Rustic Farmhouse on Lake Cumberland

Jamestown

Grant A.

SAR 3,012 total

includes taxes & fees

19 Oct - 20 Oct

A stainless steel Cuisinart grill with four burners, a side burner, and a built-in oven, set against a wooden deck with a view of a leaf-covered park.

6. Peaceful Russell Springs Home w/ Fire Pit & Pond!

Russell Springs

SAR 1,028 total

includes taxes & fees

15 Nov - 16 Nov

A white house with a red door, black shutters, and a snow-covered roof.

7. Large, Farmhouse Style Cottage near Lake Cumberland State Resort Park, Perfect for a Kentucky Summer Holiday

Columbia

SAR 904 total

includes taxes & fees

19 Oct - 20 Oct

A red rocking chair on a porch with a view of a green landscape.

8. Grandma's Cottage at Garrison Farmstead near Columbia and Greensburg KY

Greensburg

Darin B.

SAR 1,839 total

includes taxes & fees

30 Oct - 31 Oct

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Top Jamestown Hotel Reviews

Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!

10/10 Excellent

"Jared was the best host. Property was clean and inviting with all the amenities"

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

10/10 Excellent

"We spent the weekend here for fall break and loved it. The house is very nice and in a great location, just minutes from Jamestown and Russell Springs or Lake Cumberland state park. There’s plenty to do if you plan to be out and about but the house is a great place to unplug and unwind and be away from it all. Kitchen is nicely equipped, two decks are great for relaxing in a quiet location, but also tv’s and games available. The whole house is incredibly nice and clean and all the beds are comfortable. The check-in and checkout were super easy and the owner was very helpful and responded to messages. The only downside is we had to leave! We will certainly be back!"

Timber Pointe Resort

8/10 Good

"We only stayed here overnight for a new place to stay so we came in the evening and left in the morning. We didn't get to experience the amenities like swimming but the place was very pretty. One thing I didn't like was check inside the pub so when I got there it was pretty loud and hard to hear. The room was across from the pool so it was loud until quiet time and it seemed like everyone then relaxed. I would definitely stay here again but maybe get there earlier to check out the pool, fitness center, and game room. Free wifi and the ac worked really well, bed was a little hard for me but my husband liked it. Coffee in the room was Folgers so better than most"

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

10/10 Excellent

"House was perfect for our stay. We had 5 couples and brought 4 trucks and trailers with boats, We had plenty of parking , everyone had a bed and the house was within minutes of Jamestown marina and some nice local dining. Would definitely stay again!"

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

10/10 Excellent

"This cabin IS NOT in Jamestown, unlike the pinned location shows in VRBO. It is about a 25 minute drive from the center of Jamestown. Apparently it’s a VRBO issue, no fault to the host. The host was very communicative; gave clear check-in & checkout instructions. The hot tub was a great relaxing piece, the game room had a lot of options for everyone. Plenty of space in the cabin for 6 adults, the beds were comfortable, although the pull out couch kept tipping back when those guests laid their heads down. Overall great stay"

Frequently asked questions

Why book your cottage in Jamestown with Expedia?

We think that a vacay should be a piece of cake, so if you're chasing cottages in Jamestown at an affordable price, Expedia has got your back. Stick to the budget and opt for a wallet-friendly option far from the rush of the city, or splurge on a 5-star cottage to spoil your loved ones.

How can I find cheap cottages in Jamestown?

Expedia is here to help you locate cheap cottages in Jamestown. To book a superb stay in a matter of clicks, simply use our convenient filter tool to refine your search by star rating, amenities and budget.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Jamestown cottages

1. 4BR Charming Cabin Retreat | Hot Tub, Fire Pit

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

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

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

5. Restful Rustic Farmhouse on Lake Cumberland

6. Peaceful Russell Springs Home w/ Fire Pit & Pond!

7. Large, Farmhouse Style Cottage near Lake Cumberland State Resort Park, Perfect for a Kentucky Summer Holiday

8. Grandma's Cottage at Garrison Farmstead near Columbia and Greensburg KY

9. Upscale Cottage Rental for Families near Russell Creek in Greensburg, Kentucky

Find vacation rentals that suit your style

Top Jamestown Hotel Reviews

Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!

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

Baymont by Wyndham Albany

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

Sunset Ridge·Sleeps 16·Panoramic Lake Cumberland Views·3 Decks·Jamestown Marina

Timber Pointe Resort

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

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

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

Frequently asked questions

Search Cottages in Jamestown

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Jamestown cottages

1. 4BR Charming Cabin Retreat | Hot Tub, Fire Pit

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

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

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

5. Restful Rustic Farmhouse on Lake Cumberland

6. Peaceful Russell Springs Home w/ Fire Pit & Pond!

7. Large, Farmhouse Style Cottage near Lake Cumberland State Resort Park, Perfect for a Kentucky Summer Holiday

8. Grandma's Cottage at Garrison Farmstead near Columbia and Greensburg KY

9. Upscale Cottage Rental for Families near Russell Creek in Greensburg, Kentucky

Find vacation rentals that suit your style

Top Jamestown Hotel Reviews

Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!

Frequently asked questions