Holiday houses in Jamestown

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Top-rated holiday rentals in Jamestown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Monticello

4.92 out of 5 average rating, 168 reviews

Bluegrass Gables: Lake Cumberland Cottage

Relax in the forest is this amazing 4bd/2.5ba cottage. Only minutes to the Ramsey Point boat ramp, this is your base for your Lake Cumberland vacation. Bring your boat; ample parking onsite. Don't have a boat? No problem, Beaver Creek and Conley Bottom marinas are close by. House features modern amenities and a fully stocked kitchen. Enjoy the fireplace indoors or the firepit outdoors. Forest views and fresh air galore await you, especially from the hot tub! Absolutely no smoking inside or out.

Guest favourite

Home in Nancy

4.98 out of 5 average rating, 65 reviews

Prather Place,Spacious,Lake View,5min to Marina

Enjoy breathtaking lake views from almost every room in the house. Very open floor plan with huge kitchen/dining/living room space. Four bedrooms to sleep 11 comfortably plus additional reclining sofas on main level. Complete game room in basement with custom bar. The theater room has the largest of 8 TV's in the house at a whopping 65 inches. Over 2,000 square feet of decking with cable railing to not spoil any of the unobstructed year round views. This truly is "THE" Lake Cumberland rental.

Superhost

Home in Somerset

4.57 out of 5 average rating, 7 reviews

Take It Easy@The Easy Peasy

•Vintage 40's farmhouse w/fabulous private pool (closed for season)+ hot tub area •Centrally-located, 2 min. to boat ramp+ 7 to marina • Hidden speak-easy themed basement bar w/pool + poker tables, shuffle board,+ more (search home for entrance+code) •Equipped country kitchen+sunroom w/drink fridge, games,+ coffee bar. •Unique attic space for family fun (lake house+camp themed w/games+movies) • 5 BR, 2 full baths-1st retro styled w/soaking tub, 2nd w/double sink+walk-in shower • Pet friendly

Guest favourite

Home in Nancy

4.83 out of 5 average rating, 53 reviews

Little blue house on the lake

Brand new wrap around deck for 2024 for outdoor enjoyment or relax in covered sunroom. Lakeside retreat where you can unwind after a day on the lake or just enjoy peaceful country living. This charming cabin-style home features 3 bedrooms and 2 bathrooms with the primary located on the main floor and 2 bedrooms with a jack and jill bathroom upstairs. Located just a mile from a boat ramp, 6-minute boat ride to Conley Bottom or 15 minute car ride to Lee’s Ford Marina or Pulaski County Park.

Guest favourite

Tiny home in Somerset

4.84 out of 5 average rating, 31 reviews

The Tiny Swift Lake House

Looking for an enchanted get away close to the lake? Look no further. Only 5 minutes to Lake Cumberland and 5 minutes to Somerset, This TS decorated tiny is your dream come true! Walk into a Swifty's dream, with welcoming friendship bracelets! Tiny house is equipped with full size kitchen and full bathroom! Queen size luxury mattress and a pull-out sofa makes this big enough for the whole family! You will find a towel warmer, stocked coffee bar, w/d, grill and much more! This s a must see!!!

Superhost

Cabin in Nancy

4.95 out of 5 average rating, 76 reviews

Spectacular Cabin on Lake Cumberland- Amazing View

Lake view doesn't get any better than this! New cabin tucked back in the woods overlooking the main lake towards Conley Bottom Marina. Dedicated parking area for renters boat/camper with electric and water hookup. Several free boat ramps and marinas within minutes with available boat rentals, hiking trails, sightseeing and overlooks. Relax by the outdoor firepit overlooking the lake surrounded by tall trees or enjoy a cup of coffee on the patio. Visit my guidebook for local recommendation

Top Guest favourite

Home in Russell Springs

4.97 out of 5 average rating, 29 reviews

Lake Top Cabin #10

Completely remodeled lake view home at top of Lake Cumberland Marina. A spacious covered porch with a swing for those summer days and nights. 2 picnic tables and a grill for outdoor grilling days. A large deck with stunning views of the lake. Perfect for enjoying your morning coffee or evening wine after a great day on the lake. Perfect for large families or groups. Sleeps 10. Pets are welcome. Backyard is spacious for kids to play. Plenty of parking for your boats and vehicles. .

Top Guest favourite

Home in Monticello

4.96 out of 5 average rating, 53 reviews

Vacationers delight at Conley Bottom

Don’t let the price fool you. We do Vacation right in this home. Less than a quarter mile from Conley Bottom Marina, this house is great for anyone looking to get away for the weekend. Your boat can be kept in the driveway, we have a golf cart you can rent during your stay, as well, to explore the area and drive down to the marina. Conley Bottom offers everything from the boat ramp, boat rentals, water sports, fishing. Five golf courses located within a half hour of the house

Top Guest favourite

Home in Monticello

5 out of 5 average rating, 10 reviews

Lake Cumberland Luxury #2~ Lake views and hot tub.

One of Airbnb’s favorites, under new ownership! Same home same luxury~ Come enjoy the best that Lake Cumberland has to offer. This beautiful, spacious, and private home offers one of the best views of Lake Cumberland you will see. With 5 bedrooms and 2.5 bathrooms you will have plenty of space to sleep up to 10 guests—making it a perfect trip for families and friends. There is a hot tub, pool table, fire pit, cornhole and tons of games to take your stay to the next level.

Superhost

Cabin in Jamestown

4.78 out of 5 average rating, 9 reviews

Harbor Springs, Jamestown Cabin

Gather your group, you've found the right spot. This picture perfect cabin comfortably sleeps a group of 8. Whether you're visiting for water activities or looking for a cozy getaway, look no further. Conveniently located at the top of a quite street, this cabin views both Jamestown Harbor and State Dock Marina, central of Lake Cumberland. Only a 5 minute drive to dock where you will find restraunts, shopping, boat rentals, playgrounds, seasonal events, and much more.

Guest favourite

Cottage in Russell Springs

4.89 out of 5 average rating, 35 reviews

The Cozy Cottage near Lake Cumberland

Ready to stay at a unique oasis near Lake Cumberland? Come enjoy The Cozy Cottage, which is in beautiful and convenient neighborhood of Russell Springs, Kentucky - just minutes from the Houseboat Capital of the World! All of the town's amenities are just minutes away from the cottage, while also being located just 8 miles from Alligator 1 boat ramp, 10 miles from Jamestown Marina, 10 miles from Pleasant Hill, and 12 miles from Indian Hills/Alligator 2 boat ramp!

Top Guest favourite

Home in Nancy

5 out of 5 average rating, 14 reviews

Fawn Run on Lake Cumberland

Retreat to Fawn Run, a tranquil sanctuary set on over 2.18 lush acres near Lake Cumberland. This idyllic getaway boasts a lively game room equipped with board games and a TV, and a classic wood-burning fireplace for cozy evenings. Step outside to savor a barbecue, relax around the fire pit, and enjoy the serenity of the forest. Perfect for families or groups seeking a peaceful escape surrounded by nature’s beauty, Fawn Run promises a rejuvenating stay.

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What guests are saying

Luxury Lake Home! Dock Holidays Lake View Inn

5 out of 5 average rating, 14 reviews2 weeks ago

The house was perfect for our family reunion, and Teresea and Tim are incredibly kind and helpful hosts. The kitchen was well equipped with everything we needed to fix all our meals, the living area has comfortable furniture for a crowd to hang out together, and it was great to have so many main floor bedrooms with their own bathroom. We loved sitting out on the deck, and the view of the lake was even better than I'd expected from the photos. We highly recommend it and hope to return again next year ourselves!

Home in Monticello

What guests are saying

New Lakefront Luxury: Hot Tub, Arcade,Serene Views

4.98 out of 5 average rating, 88 reviewstoday

This is the most beautiful Airbnb we have stayed in to date! Between the house itself and the lake views - it was all stunning. We had 2 families staying and there was more than enough space to both hang out as a groups as well as go off on your own. The kids had a blast in the game room. The kitchen was well stocked with anything you would need and then some. And everything was labeled which was helpful to find what you were looking for. There was so much to do in the surrounding areas. We would definitely rebook if we travel back to this area!

Home in Somerset

What guests are saying

Barndo Bliss: Luxury King Suites, Spa, Fire Pit

4.99 out of 5 average rating, 76 reviews2 weeks ago

Stephanie’s barndominium is absolutely beautiful! Due to work and our schedule we decided very last minute to take a very small trip for our kids for spring break. So glad we came across this listing! It felt so welcoming as soon as you walked in the door. Beautifully decorated and more than plenty of room. Although it was only our little family staying, you could easily have two families stay together with plenty of space. I must say the beds were extremely comfortable, and having two king en-suites were so nice! The kitchen was well equipped. It was nice having both a keurig and regular coffee maker. We will definitely look into staying again!

Home in Monticello

What guests are saying

Lakeview Hideaway

5 out of 5 average rating, 21 reviews3 weeks ago

The house was clean and just as pictured. It was stocked with all necessary amenities. The view from the porch was very nice and peaceful. Lots of wildlife (most notably was a red fox and indigo bunting blue bird). Very quiet neighborhood, and very relaxing. Amanda and Jarran were both responsive and helpful. Would not hesitate to stay here again! We had cell service there with Verizon, but data on our cell was spotty. However, the wifi at the house worked flawlessly (so, no issues there). We stayed during an off-season. Would like to visit again during the lake season to better explore lake Cumberland and do some boating etc.

Home in Nancy

What guests are saying

Lake Cumberland Retreat #1 near Somerset and Ramps

4.95 out of 5 average rating, 41 reviews3 months ago

The back porch has a beautiful view. It was a joy to sit on the back porch and have dinner with my kids. The neighborhood is quiet and everyone is so nice. The owner is very respectful and gets back to you very fast on anything. Definitely would stay again.

Holiday home in Somerset

What guests are saying

23 Acre Lake Cumberland: Boats & Fishing Oasis

4.98 out of 5 average rating, 60 reviews3 weeks ago

This was a great home base for our trip. From here you can get to most of the “major attractions” around the state in under 2 hours. Very clean, comfortable, and well stocked. Smaller than I expected, but it was fine for the 4 of us. The house is closer to the road than I thought it would be. There was some road noise occasionally, but not anything too irritating. Because of the way the house sits, you don’t really see the traffic. It is away from town so it does feel rural, but close enough to go out in the morning for AMAZING donuts at Amon’s or anything else you could think of. I was impressed by the variety of options!

Farm stay in Somerset

What guests are saying

Happy Hollow Creekside Cottage

4.93 out of 5 average rating, 14 reviews4 months ago

This was such a great getaway for my family. From the moment we walked in it felt like "home". So cozy and welcoming. Dottie and Elliot even went the extra step to make my husbands birthday special, by putting up a banner, balloon and got him a DELICIOUS cake that we devoured as soon as we came in. We have a 3 month old and 13 month old and they slept great there! We all did! 10 out of 10, this place was AMAZING! We can't wait to get back! Thank you both for making our stay so amazing

Home in Columbia