Holiday rentals 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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Superhost

A comfortable bedroom is present, featuring a neatly made bed covered with a light quilt. A decorative pillow adds a touch of accent. Natural light enters through a window with blinds, and a stylish light fixture illuminates the room. A nightstand with a lamp is positioned beside the bed.

Home in Pikeville

4.83 out of 5 average rating, 144 reviews

Living The Dream

*If you book for 7 days or more, you will receive a 20% discount off your stay. Our home is perfect for your visit in Pikeville, especially for a large group. Enjoy the complete home with 3 bedrooms, 2 full baths, a complete kitchen with dishwasher, & washer/dryer. You'll enjoy a good nights sleep in a quiet space on high quality mattresses. We are located just down the street from a Food City. We have free WIFI & a Smart TV (NO CABLE TV). We’re a short 5 minute drive from downtown Pikeville.

Guest favourite

The kitchen features a spacious island with four cushioned stools, modern pendant lighting, and a distinctive SMEG fridge. Clean countertops offer ample prep space, while stylish green tile backsplashes add a chic touch. The area is well-lit and flows seamlessly into the living space.

Flat in Pikeville

4.94 out of 5 average rating, 118 reviews

Walk to dinner, UPIKE, hospital•3 Lux Bed• Balcony

Upstairs-The Eccentric Privy is the best of the best worlds. Retro, glam & quirky! You’ll obsess over the thought put into each room & even get some inspiration. Extra amenities include… Outdoor deck Quartz Countertops Luxury tile SMEG fridge Smart thermostat Bathroom Bluetooth speaker USB outlet in each room Soft close doors & drawers in kitchen & bathroom 550 TC cotton bed sheets and pillow covers Allergy defense, antimocrobial pillow protectors Tankless water heater for endless hot water

Guest favourite

The cabin's exterior is softly illuminated at twilight, featuring a welcoming entrance with colorful doors. A stone pathway leads to a cozy seating area surrounded by greenery and potted plants. The car parked in the foreground adds to the homey feel of the location.

Cabin in Prestonsburg

4.88 out of 5 average rating, 102 reviews

The Eagle's Rest Country Cabin

Welcome to the Eagle's Rest! This family & pet friendly cabin is nestled outside of Prestonsburg. Mountainous escapes of sunrises & sunsets w/access to a private 20-acre mountain for hiking & birdwatching. Enjoy plenty of 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/DirecTV & T-Mobile Int. Located near StoneCrest Golf Course, Jenny Wiley State Park, & Sugarcamp MtnTrails & Middle Creek Battlefl

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

4.99 out of 5 average rating, 103 reviews

The Red Dog Chalet Couples Retreat w/ Hot Tub

Trailer access pull-thru private parking area with a beautiful lighted walking bridge that leads you to the chalet. A beautiful getaway with a spiral staircase leading you to the 2nd story covered porch with a wraparound walking deck. Large firepit area with dried fire wood. Large 12ft by 12ft hammock beside fire pit area. Two person copper tub; private outdoor shower; hot tub and large bed swing. Loft bedroom. Free WIFI. Park Series charcoal grill outside. Buffalo Mt trailhead 1/2 mile.

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 out of 5 average rating, 50 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

Top guest favourite

A modern black house is set on a rocky landscape, surrounded by lush greenery. A wooden post carved with bear figures adds natural charm. Large windows invite light into the home, enhancing the connection between indoor and outdoor spaces.

Home in Wellington

4.99 out of 5 average rating, 125 reviews

Luxury Cliffside Hammock House

Escape to a modern luxury hammock oasis: with cozy indoor & outdoor loft-net hammocks, memory foam beds with MyPillow pillows for supreme comfort, and MyPillow towels enhancing the spa-like bathrooms featuring rainfall showers and body jets. Adventure awaits with a private trail into Daniel Boone National Forest, a hot tub, and a pool table. This space isn't just a stay but an experience, designed for those seeking luxury, comfort, and a touch of adventure. Not Suitable for children.

Top 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

4.96 out of 5 average rating, 116 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.

Superhost

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

4.94 out of 5 average rating, 124 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.

Guest favourite

A cozy living area features warm wooden walls and a gray sofa, complemented by decorative pillows. A blue accent chair adds a pop of color, while a large plant brings a touch of nature indoors. Light streams in from a skylight above.

Cabin in Pikeville

5 out of 5 average rating, 25 reviews

Inspiration Station

Inspiration Station at Harvey's Hideaway Haven is designed to uplift your spirit and ignite your inner drive. You will be immersed in nature, surrounded by the beauty of the wilderness. While this offers a peaceful escape, please be aware that you may encounter local wildlife, including bugs, bees, and other creatures that share this natural setting. Located just 9 miles from Pikeville Medical Center, Upike and The Appalachian Wireless arena!

Top guest favourite

A charming cabin is nestled among the trees, featuring a wrap-around porch with seating. The wood exterior and sloped roof complement the natural surroundings. The gravel path leads to the entrance, enhancing the inviting atmosphere of the woodland retreat.

Cabin in Wellington

4.97 out of 5 average rating, 127 reviews

Luxe Glamping A-Frame Cabin-Porch-Hammock-Dogs ok

Your forest cabin awaits at Nestled Inn cabin, relax, unplug, unwind, and experience KY’s countless natural resources. Experience the best of Daniel Boone National Forest, Cave Run Lake and Red River Gorge. Our 2 bedroom 1.5 bath cabin is fully equipped cabin with all the amenities, smart TV, Wifi and more. Escape to nature in style, but please remember we are in the woods that may mean you will see wildlife and the occasional insect or bug.

Top 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

4.99 out of 5 average rating, 148 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.

Top guest favourite

The exterior of the blue cottage is showcased, featuring a covered front porch with a railing and an entry door. Surrounding the property, trees provide partial shade, while the landscaping includes a gravel area. A vehicle is parked nearby, contributing to a welcoming atmosphere.

Cabin in Davella

5 out of 5 average rating, 39 reviews

Blue Moon at Airport Cottages

Blue Moon is a featured cottage available at Big Sandy Regional Airport. Conveniently located close to Jenny Wiley State Park. Just a short distance from Inez, Paintsville and Prestonsburg. Take it easy at this unique and tranquil getaway. Enjoy the mountains of Eastern Kentucky with us and all things local 💙