Holiday houses in Dewey Lake

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Top-rated holiday rentals in Dewey Lake

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

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Guest favourite

Cabin in Prestonsburg

4.88 out of 5 average rating, 117 reviews

The Eagle's Rest Country Cabin

Welcome to The Eagle's Rest! This family & pet friendly cabin is nestled just outside of Prestonsburg. Mountainous escapes of sunrises & sunsets. Enjoy family time w/a game room featuring a bar, billiard table, & dart board. Garage w/fire pit for entertaining or a small RV/Camper! Smart-Tv’s w/YouTubeTV & T-Mobile Int. Located near StoneCrest Golf Course. Put on your hiking boots for Jenny Wiley State Park, & Sugarcamp Mtn.Trails & Middle Creek Battlefield. Mountainous air & bird watching await.

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Guest favourite

The exterior of a wooden home is showcased, featuring a covered front porch with steps leading up to it. A gravel pathway and a welcoming sign are visible, surrounded by greenery. Large windows allow natural light into the space.

Cabin in Martin

4.96 out of 5 average rating, 46 reviews

Cecelia Ann Tiny Home 1/1 Quiet

Kick back and relax in this calm, stylish space. Quiet area Boho vibes, home was completed in November 2023 all new furnishings, complete kitchen, inside washer and dryer. All appliances, Keurig coffee pot for either single cup or entire pot. Covered front porch, off street parking. Close to several area hospitals, 16 miles to Pikeville and Appalachian Wireless Arena. Close to riding trails for 4 wheelers or side by sides. Less than 2 hours from casino, little over hour away from Red River Gorg

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Top Guest favourite

The exterior of the chalet features a two-story structure surrounded by lush greenery. A covered porch extends from the second level, and a staircase leads down to the landscaped yard. Pathways and railings create a welcoming access to the home.

Treehouse in Williamson

4.97 out of 5 average rating, 134 reviews

The Red Dog Chalet Couples Retreat w/ Hot Tub

Private parking area with a beautiful covered walking bridge that leads you to the beautiful getaway with a spiral staircase taking you to the 2nd story covered porch areas with a wraparound walking deck. Queen size loft bed. Kitchenette area on main floor. TV/WIFI. Enjoy the two person copper tub. Under the chalet, there is the private outdoor shower; hot tub and bed swing. Large firepit area with fire wood. Large 12ft x 12ft hammock behind fire pit area. Park Series charcoal grill outside.

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Top Guest favourite

A custom hanging bed is framed by a nature mural featuring tall trees, creating a serene ambiance. Soft bedding and decorative pillows add comfort. A sliding glass door leads to a private deck with seating, allowing for views of the lush surroundings.

Home in Inez

5.0 out of 5 average rating, 74 reviews

Luxury Creekside Cottage

Come soak up nature and get away from the hustle and bustle, check the completely remodeled cottage in downtown Inez, Ky The vacation rental features a luxurious interior, a spacious deck, and awe-inspiring views of the mountainous landscape. Spend your days walking the trails, hiking or riding ATV’s through the mountains. For a more relaxing adventure, take a short ride for the best elk viewing in the state. Sleeps 8 guests; 2 bedrooms; 1 Bathroom; https://www.airbnb.com/slink/VNxk38u6

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Top Guest favourite

A cozy seating arrangement is presented with two light-toned sofas, complemented by decorative cushions. A round table is positioned between them, enhancing the living space. The room features soft lighting, a mirrored reflection of the bedroom area, and a door leading to another room.

Apartment in Stanville

5.0 out of 5 average rating, 13 reviews

Cozy Studio

Welcome to your perfect home away from home! This 1-bedroom, 1-bath rental is designed for comfort and convenience, featuring a fully equipped kitchen to prepare your favorite meals, an in-unit washer and dryer for easy laundry, and Wi-Fi and a TV for entertainment and relaxation. Enjoy a peaceful stay with the privacy of your own driveway, making parking hassle-free. Whether you’re here for work or leisure, this cozy space has everything you need for a stress-free and enjoyable stay.

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Guest favourite

A spacious living area features a comfortable brown leather sofa and a circular chair. A 58" TV is mounted on the wall, accompanied by a wooden entertainment unit. Natural light filters through sheer curtains, and decorative artwork is displayed on the walls.

Home in Prestonsburg

4.94 out of 5 average rating, 143 reviews

The Shotgun House

Enjoy your stay at the Shotgun house located in the heart of Prestonsburg within walking distance to a popular restaurant and downtown shopping. This cozy house offers a 58" TV and playstation in the living and also a 50" TV in the bedroom. Relax outside on a covered porch and enjoy the occasional local live music. Located close to the Prestonsburg Passage Trail, Mountain Arts Center, Middle Creek National Battlefield, Pikeville Exp Center and a short drive to the Red River Gorge.

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Top Guest favourite

The cabin is situated beside a tranquil pond, surrounded by lush greenery and gentle hills. The structure features a metal roof and combines wooden and red exterior elements. A gravel path leads to the entrance, which is framed by small shrubbery.

Cabin in West Liberty

4.98 out of 5 average rating, 91 reviews

Bowman Pond Cabin, spacious 1 bdrm open floor plan

Setting back about 1/2 mile into our 375 acre farm is our Bowman Cabin. Kick back and relax in this beautiful open concept cabin on a small pond. It has many comforts of home such as electricity, heat/ac, running water. There is no wi-fi and cell phone signal varies however there is a tv w/antenna and a DVD/Blu-ray player. There is plenty of hiking . Laurel Gorge, Red River Gorge, Cave Run Lake and Grayson Lake are just a few attractions within short driving distance from us.

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Guest favourite

The exterior of a charming home is framed by a large tree and well-maintained shrubs. The house features a combination of brick and siding along with a welcoming yellow front door. A grassy lawn complements the overall inviting appearance.

Home in Paintsville

4.98 out of 5 average rating, 44 reviews

The Whitt House

A classic charmer, The Whitt House exudes character and is sure to make you feel right at home! With three bedrooms, a loft sporting a comfy futon, family room, living room, and fenced back yard, The Whitt House has room for the whole family to spread out and enjoy your time in Paintsville. Centrally located in a wonderful, people and dog-friendly neighborhood, the home is within walking distance to downtown and is perfect for enjoying all that Paintsville has to offer.

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Guest favourite

A charming cabin is set against a lush, green backdrop, featuring a red roof and stone-accented front porch. The porch is lined with wooden railings and includes a seating area. An American flag waves gently in front of a grassy lawn, inviting guests to enjoy the outdoors.

Cabin in Hagerhill

4.93 out of 5 average rating, 138 reviews

Spacious 3 bedroom cabin with hot tub

Located in Paintsville, Kentucky. Gather around the wood fireplace and enjoy a game of pool. There are 2 smart tv's to binge your favorite shows on. Or unplug and and take in the sights on the wrap around porch with a good book. Enjoy the outdoor kitchen and firepit, then hop in the 8-person hot tub. located just 5 minutes from hiking trails, Paintsville lake state park and golf course, and local eateries . Walmart is conveniently only 8 minutes away.

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Guest favourite

A vibrant mural depicting mountains and a sun creates a striking backdrop. A cozy seating area is featured in front, with a teal couch contrasted against a wooden floor. A stylish lamp adds a touch of warmth to the space.

Holiday home in Prestonsburg

4.96 out of 5 average rating, 189 reviews

The Burg

Enjoy local venues, The MAC, Planetarium, Jenny Wiley Lake, 1620 Distilling Company, hiking, biking, wildlife, local artisans and crafts. Home to Loretta Lynn's, Butcher Holler. Civil War History. Close to downtown shopping, walking distance to dining, coffee shops, and bakery. There are 2 rather short flights of stairs to access this unit.

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Top Guest favourite

The living area showcases a wood-paneled interior with a dining table and chairs adjacent to two cozy sofas. A television is positioned for easy viewing, and various decorative items, including mounted wildlife, are displayed on the walls and shelves, creating a rustic atmosphere.

Cabin in Louisa

4.98 out of 5 average rating, 293 reviews

Workman's Wildlife Haven

Vacation cabin (800 SF), secluded on 300 acre farm, hiking trails, wildlife viewing, 3 fishing ponds, 2 picnic areas, great scenery located in hills of eastern Kentucky. Fully furnished with wood burning fireplace, 1 bunk bed, 1 Queen Size bed/mattress, (sleeps 4). Nightly.

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Guest favourite

A grand facade of the home is showcased under a clear blue sky, featuring a large arched entrance framed by elegant landscaping. A decorative bronze fountain stands prominently in the foreground, surrounded by a neatly paved driveway that leads to the entrance.

Home in Prestonsburg

5.0 out of 5 average rating, 17 reviews

Mountain Manor Luxury Estate

Our fabulous Mountaintop get-away (now under new management) is nestled on nearly 2 acres atop Stonecrest Golf Course. This sprawling property is perfect for family gatherings, receptions, bonding retreats, and more – we’ve even had weddings!

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