Vacation rentals with outdoor seating in Jamestown

4.95 out of 5 average rating, 235 reviews

A charming log cabin is depicted with a green metal roof and a welcoming front porch. An American flag is displayed prominently, while a patio umbrella provides shade over a table and chairs. Surrounding greenery enhances the natural setting.

Cabin in Liberty

Sandy Acres Hobbit - Near Galilean Home - Liberty

Sandy Acres Hobbit Cabin is a one bedroom 2 Log Beds with Loft via ladder... nestled in the majestic hills of Kentucky, on 30 Acres 5 miles south of Liberty. Family owned and run. Our non-smoking, pet friendly ($20), log cabin has central heat and air conditioning, Log Beds, with all the comforts of home. Cable TV-DVD player and High Speed WI-FI service. Quiet getaway. Perfect for the single, couple or small family looking for adventure. SandyAcresCabins Liberty, KY. Click on Picture for More.

4.92 out of 5 average rating, 175 reviews

A cottage is seen surrounded by vibrant autumn foliage, with a gravel driveway leading to the entrance. The architecture features a gabled roof and a spacious front porch, providing an inviting entry point to the home.

Home in Monticello

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.

4.95 out of 5 average rating, 219 reviews

A covered deck area features comfortable seating and overlooks a lush landscape with a serene lake in the distance. Sunlight filters through the trees, illuminating the wooden flooring and creating a peaceful retreat for relaxation.

Tiny home in Monticello

*Tiny LakeView Cottage* Pets welcome! Kayaks

We welcome your fur babies!! ATV trail to lake! Ice maker! Coffee! Adorable tiny house with two decks & bonfire pit overlooking 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. On a dead end street, so very peaceful. Also has an ATV trail to lake!! Kayak rental is available for $25. per day/per kayak. Pet fee $50/$75 per stay.

The exterior of a new construction home is visible, featuring a blend of wood and dark siding. A spacious porch, supported by wooden beams, invites relaxation, while tall trees surround the property, enhancing the sense of seclusion. Natural landscaping complements the tranquil setting.

5 out of 5 average rating, 19 reviews

Onyx House

Take a break and unwind at this peaceful oasis, surrounded by nature. Minutes to Lake Cumberland State Resort Park & Marina and Halcombs Landing Boat Ramp ‘Dam’-you’ll have easy access to the water. Outdoor seating with 3 decks, outdoor tv, and fire pit allows for great social entertainment and a perfect place to unwind. 2 private bedrooms downstairs (queen), with a 4 bed (full) loft upstairs. 2 bathrooms down stairs-one with walk-in shower, one with tub/shower. The kitchen is fully equipped.

A spacious living area features a large leather sectional sofa and a teal armchair, complemented by a decorative ottoman. A flat-screen television is mounted on the wall opposite a large window, with natural light illuminating the light wood flooring.

5 out of 5 average rating, 8 reviews

Lake Vibes

Your Lake Cumberland retreat! Located just minutes from Lake Cumberland, this home offers the perfect escape for your next getaway. Located just 2 miles from Jamestown Marina, with easy boat access and great proximity to fantastic restaurants, and recreation, this is the perfect spot for those who love the outdoors, adventure, or relaxation! The home offers a horseshoe drive for an easy in and out, and features a garage on site for boat storage, as well as an out building, both with electric.

A screened porch featuring a mix of red and blue chairs arranged around a table, surrounded by large windows that overlook a lush green setting. Soft lighting is provided by hanging bulbs, enhancing the inviting space.

4.92 out of 5 average rating, 13 reviews

Jamestown - KY Lake Cottage | Boat Parking

Welcome to your seasonal getaway at Harbor Springs Cottage near beautiful Lake Cumberland! Inside, our three private bedrooms offer a haven of comfort for you and your guests, ensuring a restful night's sleep after a day of lake time. Whether you're seeking a romantic retreat, a family getaway, or a solo escape, Harbor Springs Cottage has got you covered. ☆Book your stay at Harbor Springs Cottage today and discover why life truly is better by the lake. Your perfect retreat awaits!☆

4.91 out of 5 average rating, 64 reviews

The exterior of a renovated A-frame cabin is surrounded by lush trees. Large glass windows provide a view into the interior. A spacious deck features comfortable seating and a patio umbrella, inviting relaxation in a natural setting.

Cabin in Jamestown

Renovated cabin minutes to Jamestown Marina

Cozy, Renovated A Frame Cabin. Updated 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! Absolutely no pets.

The exterior of a modern blue house is showcased, featuring multiple large windows that allow natural light to enter. A freshly paved driveway leads up to the home, while a sign indicating the house number is positioned nearby. Lush greenery surrounds the property.

5 out of 5 average rating, 16 reviews

The Bourbon House

Take it easy at this unique Kentucky Bourbon themed getaway only 10 minutes away from Lake Cumberland via the Jamestown Marina. The Bourbon House has two queen beds in their own bedrooms and a full sized pull out sofa with 2 full bathrooms. It has a fully equipped kitchen but is only 5 minutes away from Jamestown Square with 3 different delicious restaurant options. Enjoy the peace of being in the country on the back patio facing the woods, with a fire in the fire pit.

The kitchen features a modern design with white cabinets and granite countertops. Stainless steel appliances are showcased, alongside open shelving displaying various dishware. Four blue metal stools are positioned around the kitchen island, and a window allows natural light to enter.

4.92 out of 5 average rating, 49 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!

Superhost

A charming exterior view of a house features a welcoming front porch with two comfortable seating areas. Lush green grass surrounds the property, and large trees provide shade, creating a serene outdoor space. The entrance is highlighted by a prominent front door with a lantern above.

4.9 out of 5 average rating, 20 reviews

Cozy Lake Time Retreat

Kick back and relax in this calm, stylish space. Perfect location for visiting the lake or family. Come stay at our 3 bedroom 2 bath home that is centrally located in Jamestown for easy access to multiple docks. The home is adequately furnished with everything you would need to enjoy your time at Lake Cumberland. It sits in the 1.5 acres so there is plenty of room to gather and enjoy the outdoors. *Master bedroom upstairs has very low ceilings.

4.96 out of 5 average rating, 115 reviews

A cozy fire pit area is surrounded by several rustic chairs, positioned on a gravel surface. The serene Cumberland River can be seen in the background, bordered by lush greenery and trees, creating a peaceful outdoor setting.

Cabin in Burkesville

The riverside Cumberland Cabin

A sweet little remote cabin located in Burkesville directly on the Cumberland River. It has a total of four queen beds. Renovated inside and out with two fire pits. Outstanding coffee bar included. It has a wifi booster and a full lineup of sports channels on Dish Network. It is the perfect get away to simply unplug and reset! 11 miles to Bodock Farms wedding venue. 19 miles to Sulpher Creek , Mikes landing and Dale Hollow State Park.

A covered outdoor seating area features a dark wicker furniture set, including four armchairs with soft cushions and a matching coffee table. A large area rug with a blue and white pattern grounds the space, while potted plants add greenery.

4.97 out of 5 average rating, 29 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!

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House rentals with outdoor seating

4.92 out of 5 average rating, 13 reviews

A charming farmhouse is surrounded by lush greenery, with a spacious front yard. The entrance features two wooden doors flanked by hanging flower pots, leading to a covered porch adorned with blue seating. A concrete pathway guides visitors to the entrance.

Home in Albany

Elisi's Cozy Nook 3.2 mile from Marina Rowena.

NatalieRating, 5 stars3 weeks ago

Great place to stay to get away. Country setting with great views. Very quiet and relaxing place. The house was perfect for us. Kitchen is fully stocked with everything you would need. Very close to Rowena Marina. We will definitely be back to stay.

5 out of 5 average rating, 24 reviews

A shaded outdoor dining area features a table surrounded by chairs, set on a wooden deck. String lights hang overhead, and the expansive view of the lake and surrounding hills is visible in the background, enhancing the serene outdoor experience.

Home in Russell Springs

Welcome to your Dream Lake Home

KrissaRating, 5 stars2 weeks ago

We had such an amazing stay at Samatha’s! She was so friendly and accommodating. She worked around all of our needs since we came out of state, we had a blast! The view was also breathtaking!

4.94 out of 5 average rating, 128 reviews

The cottage features a green metal roof and a welcoming front porch with multiple wooden rocking chairs. Two planters are positioned at either side of the entrance, and a outdoor grill is visible near the porch. A gravel path leads up to the door, with lush greenery in the background.

Home in Albany

Avery Acres

PamelaRating, 5 stars3 weeks ago

This is our favorite place to stay. The address is nice. The house is clean. The host is super! We'll be back!

5 out of 5 average rating, 22 reviews

A living room features fully reclining furniture arranged around a patterned rug. Two lamps illuminate the cozy seating area. A wall sign reads 'LAKE LIFE.' An open view leads to the dining area, which is visible through a wide entryway.

Home in Russell Springs

Ina's Place

LauraRating, 5 stars1 week ago

Excellent stay. Met all our needs and then some. Only regret is that we didn’t stay long enough. We were in town for a wedding. Wish we had planned a longer stay. Very comfortable home that managed our multigenerational family (including small children) extremely well.

4.99 out of 5 average rating, 78 reviews

A modern kitchen features an island with seating for five. Stainless steel appliances and ample cabinetry create a functional workspace. Soft lighting enhances the natural wood flooring, while a subtle arrangement of plants adds a touch of greenery. The layout promotes an inviting atmosphere for cooking and gathering.

Home in Monticello

Barndo Bliss: Luxury King Suites, Spa, Fire Pit

EmilyRating, 5 stars1 month ago

It was the perfect house for our weekend getaway! The hosts were very helpful and responded quickly. The house was spacious, clean and was fully stocked! We couldn’t have picked a better house for our girls weekend!

5 out of 5 average rating, 17 reviews

The exterior of the Riverside Retreat features a charming two-story home with a gabled roof and a welcoming entrance. A stone pathway leads to the front door, framed by subtly lit landscaping and blooming flowers. Lush greenery is visible in the background, enhancing the tranquil setting.

Home in Peytonsburg

Riverside Retreat

ShirleyRating, 5 stars1 week ago

Both the house and hosts were amazing! The place looked great online but was even better in person. It was evident that so many things were very well thought out. It was also much closer to the river than I envisioned. The view from the patio was lovely. We used all the bedrooms and brought a cot to turn the upstairs reading loft into another sleeping space. There was also plenty of space to have used the cot in the downstairs game area. The dining table seats six, but we brought a card table with us to extend it to make more room. There were plenty of folding chairs and a bench to use for extra seating. The patio had a picnic table and several seating options. The downstairs patio had at least 10 comfy stackable chairs. There is no TV on site, but we had a small projector that connected to a cell phone that we were able to display on one of the large walls in the basement. We used the patio chairs to make our own theater seating.

5 out of 5 average rating, 20 reviews

A spacious living room is highlighted by a large 65-inch TV on a wooden entertainment unit. A dark sectional sofa is arranged around a patterned area rug with a plant in a gold pot nearby. Natural light enters through a window, creating a bright environment.

Home in Monticello

Home 0.2 miles from boat ramp with game room

JamieRating, 5 stars3 days ago

We had a great stay here! The place was very clean and was the perfect, cozy, lake house to crash after a day on the lake. We also enjoyed the games and karaoke in the garage when it rained. We had a lot of fun! This may be our new go to place if it’s available as we have family close by that come down to the lake every year. We felt like it was very affordable for what it was as well!

4.88 out of 5 average rating, 65 reviews

A charming house is set against a backdrop of lush greenery, surrounded by tall trees. The well-maintained lawn features a manicured appearance, while the welcoming front porch is highlighted by a red entry mat. A clear blue sky complements the serene forest setting.

Home in Nancy

Waterfalls, fishing pond, lake view, and 8 acres!

DoraRating, 5 stars6 days ago

Beautiful location, waterfalls were amazing, little pond was very entertaining for the kids! Little bit of a drive to go to town, but plenty to do while in town! Driveway can be difficult-not Justin’s fault…Kentucky is mountainous! The house was cozy, we loved eating dinner on the back porch, we would come back!

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Apartment rentals with outdoor seating

An outdoor patio area features a wooden fence surrounding a seating arrangement with several chairs and a table. Two large planters are positioned at either end, and a grill is visible nearby. Lush greenery and a gravel pathway are seen in the background.

4.88 out of 5 average rating, 51 reviews

New near Jamestown Dock - B

TerryRating, 5 stars2 weeks ago

We have rented this apartment quite a bit and it is always clean and comfortable!

A stackable washer and dryer is positioned against a light yellow wall. The area features a wooden floor with two textured rugs in the foreground. A doorway in the background leads to another room, while a hints of a bed and dresser are visible.

Apartment in Nancy

Cozy in Kentucky

LisaRating, 5 stars20 months ago

These accommodations were just what we were hoping for! Our stay was very comfortable and was located in a quiet neighborhood. We had privacy and everything that we needed to make our stay an excellent one! Sitting on the deck and watching the sunset was an extra and unexpected treat! It is obvious that the host has thought of everything to make her guests comfortable and welcome! I would recommend this Airbnb to anyone. It was an added bonus that it is less than 2 miles from the local marina on Lake Cumberland. We were so pleased with our choice!

A modern kitchen is equipped with stainless steel appliances, including a microwave and an oven. Wooden cabinets provide ample storage space, while a countertop offers a workspace for meal preparation. A window allows natural light, enhancing the clean and functional layout.

Apartment in Albany

Spacious cozy beautiful getaway.

MichaelRating, 5 stars3 months ago

Thanks for hosting us u have a great place and it fits our needs

An indoor pool area features an elongated pool with clear water, surrounded by light-colored walls and several lounge chairs. A handrail provides access to the water, while large windows allow natural light to fill the space.

Apartment in Russell Springs

4.33 out of 5 average rating, 9 reviews

Resort Clubhouse

JessicaRating, 5 stars3 weeks ago

My family really enjoyed the space for our trip to the lake. The hosts accommodated space for our boat when we asked. It was so close to a great boat ramp, we were at the lake in less than 4 minutes. My kids really enjoyed the heated indoor pool after a day at the lake. We actually really enjoyed being in the RV park where there were other kids to play with and it was so quiet and peaceful. The hosts stopped by while we were sitting on the porch to make sure we didn’t need anything. The bedrooms had plenty of space. No complaints, such a great space we will very likely book again in the future! Thank you for having us!

An outdoor patio area features a seated arrangement with several metal chairs surrounding a table, complemented by wooden planters. A grill is positioned nearby, while a wooden fence offers an enclosed space, and greenery is visible in the background.

5 out of 5 average rating, 38 reviews

New near Jamestown Dock - A

SheilaRating, 5 stars1 week ago

Surprisingly cozy and comfortable. The beds were the best part. So comfortable!

A spacious studio bedroom features a king bed with neutral bedding and decorative pillows. Two bedside lamps provide soft lighting. A wall-mounted television and a decorative console add function, while a colorful area rug creates warmth on the wooden floor. Blue accents enhance the room's design.