Vacation rentals in Jamestown

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Top-rated vacation rentals in Jamestown

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Guest favorite

Tiny home in Monticello

4.96 out of 5 average rating, 166 reviews

Adorable Tiny LakeView Cottage with kayaks!

Totally remodeled inside and out! We welcome your fur babies!! Adorable tiny house with a deck & bonfire pit overlooking a spectacular view of Otter Creek on Lake Cumberland. It is located in Monticello, Ky in a rural part of the area. It’s about 12 minutes to town. There is very close (driving distance) swimming access, kayaking, boating, boat ramps, fishing & marinas. Plus, your likely to see lots of wildlife. I have kayaks available for a small daily fee to rent. Pets allowed! $50/$75fee.

Jun 12 – 19

G$31,173 GYD per night

Guest favorite

Home in Campbellsville

5.0 out of 5 average rating, 218 reviews

Hubbard Hill Lake House - A Fisherman's Dream!

Newly renovated! Charming lake house with open floor plan and spacious living area. Quiet, country setting surrounded by colorful maples, large magnolia trees and plenty of nature. Conveniently located less than 1 mile from Green River Lake and minutes away from Campbellsville University. Full size bed in bedroom, queen size bed in common area and queen size air mattress available. Complimentary coffee bar and snack drawer. Perfect for a weekend fishing trip or a week long family vacation!

Feb 15 – 22

G$21,407 GYD per night

Guest favorite

Tiny home in Nancy

4.89 out of 5 average rating, 57 reviews

Cabin near Wolf Creek Marina and public boat ramps

Tiny home near Lake Cumberland, Wolf Creek Marina (4.5 miles) Dudley boat ramp (1.2 miles). Beach Grove boat ramp (1.5 miles) Harris grocery (3 miles) Mill spring battle field visitors center is close by (15 miles) 30 minute drive to the Somerset, which has breweries & restaurants. Opening soon Horse Soldier bourbon!! Hour drive to Cumberland falls park. It has a bedroom, kitchen and full shower. Bring your boat and your furry friends to our peaceful tiny home. We hope to see you soon!

Oct 24 – 31

G$14,914 GYD per night

Guest favorite

Home in Jamestown

4.83 out of 5 average rating, 23 reviews

Lake Life Dot Calm (Slip Available)

Welcome to your new peaceful retreat less than 2 miles from Jamestown Marina and Lilly Creek boat ramp. SLIP RENTAL available. ROOM TO PARK your boat and trailer in the driveway! Take a walk down the street (or ride one of our bikes) to see gorgeous lake views! This 3 bedroom, 3 bathroom house has what you need for your stay! Each bedroom has its own full bathroom. Remodeled kitchen, game room in the garage, smart TVs, great back deck, and much more!

May 10 – 17

G$29,530 GYD per night

Guest favorite

Apartment in Jamestown

5.0 out of 5 average rating, 11 reviews

Lake Escapes on the Square

The whole group will be comfortable in this spacious and unique space located right on the square in Jamestown. Bedroom 1 - Queen Bed Bedroom 2 - Full Bed Located 3.5 miles from Jamestown Marina, 12 miles to Wolf Creek Dam, 13 miles to State Dock, 0.8 miles to Dollar General Market, walking distance to Reel Java, Giovanni’s Pizza & Snap’s Soda Shop! 2 parking space maximum NO ROOM FOR BOATS OR TRAILERS This apartment is located upstairs!

Jun 8 – 15

G$21,919 GYD per night

Guest favorite

Cabin in Jamestown

4.86 out of 5 average rating, 36 reviews

Renovated cabin minutes to Jamestown Marina

Cozy renovated cabin. New kitchen with large island and eat in area. Updated bathroom. One bedroom downstairs with queen bed. Loft upstairs with two additional queen beds. 2 smart TVs. WiFi better than you can find in the city. Perfect getaway close to Lake Cumberland, Lily Creek Ramp or Jamestown Marina. Room to park a small boat. Large wrap around porch and fire pit make for perfect outdoor space. Come enjoy our home away from home!

Oct 9 – 16

G$20,419 GYD per night

Guest favorite

Home in Science Hill

4.97 out of 5 average rating, 106 reviews

TT’s Treehouse

Cozy studio guesthouse with beautiful oak vaulted ceiling overlooking scenic woods and creek just 10-15 minutes from boat ramp on Lake Cumberland. Covered porch around guesthouse with gas grill access. Kitchen fully stocked. Full size sofa couch, and 2 full size floor mattresses in loft. Free wifi available. Onsite boat parking available. Fire pit and fire table available-both outside. No smoking.

Aug 8 – 15

G$25,600 GYD per night

Guest favorite

Tiny home in Jamestown

5.0 out of 5 average rating, 11 reviews

New cabin on 3 acres sleeps 6 only 3 mi from lake

We are pet friendly! Come stay with us in our new cabin on our 3 acre property in Jamestown just 3 miles from Jamestown dock. Sleeps 6 with sleeper sofa. Plenty of truck and boat parking. Great for family reunions and fishermen. Plenty of outdoor activities. We have Volleyball, Badminton, Cornhole Youth Soccer,and more! All pets must be crated when left alone. NO EXCEPTIONS!

May 21 – 28

G$24,830 GYD per night

Guest favorite

Cabin in Columbia

4.88 out of 5 average rating, 168 reviews

Treehouse - Relaxing For Couples - Fishermen

This Treehouse overlooks a field where you may see deer grazing and turkeys gobble. The cabin structure is built on the 2nd story with a cedar swing below & outside chairs to enjoy a peaceful evening by the fire pit. There is a covered porch & deck to watch the sunset then see the stars and moon rise. Comfortable space inside to relax with a good book or movie.

Feb 22 – Mar 1

G$18,695 GYD per night

Guest favorite

Cabin in Russell Springs

4.97 out of 5 average rating, 30 reviews

The Happy Place-Adorable Cabin Near LakeCumberland

The Happy Place is located just above Lake Cumberland Marina, less than a half mile to the water! This comfy cabin is perfect for both indoor and outdoor activities. Curl up on the sofa with a book, sit on the rocking chairs on the deck with coffee and enjoy the sounds of nature, or hop on your boat for a wonderful afternoon on the lake!

May 28 – Jun 4

G$21,348 GYD per night

Guest favorite

Cabin in Jamestown

4.94 out of 5 average rating, 97 reviews

On Cabin Time - Lake Cumberland Jamestown

Log cabin sitting on a hill. You can watch the deer in the field across the road, enjoy sunsets or sun rises with the wrap around porch! On Cabin Time is perfectly located 2 miles from a Clifty Creek boat ramp (on same road as cabin), just a short ride to State Dock & a easy drive to Jamestown or Russel Springs Restaurants and Shops!

Nov 1 – 8

G$24,751 GYD per night

Guest favorite

Guest suite in Columbia

4.95 out of 5 average rating, 106 reviews

Welcome to The Nest. Beautiful hill top apartment

The Nest is a beautiful open plan apartment overlooking the rolling country side of Adair County, KY. After a day on the lake or visiting one of our local colleges you can stretch out in the roomy fully equipped living/dining area or relax on the bedroom balcony.The Nest has a Queen bed and queen sleeper sofa available.

Jun 20 – 27

G$19,175 GYD per night