Holiday houses in Prestonsburg

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Top-rated holiday rentals in Prestonsburg

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

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Guest favourite

Home in Van Lear

4.8 out of 5 average rating, 15 reviews

The Bentley with Free Parking

Bring the whole family to this great place with lots of room for fun. The huge front porch provides the perfect place for morning coffee or evening drinks. The backyard patio with portable fire pit is a great place to gather and look at the stars. The spacious sunken family room with fireplace provides the perfect ambience for any occasion. The master suite with a huge whirlpool tub creates a Spa like atmosphere. The kitchen includes stainless steel appliances and High end Mouser Cabinetry.

31 Jan – 7 Feb

$3,422 AUD total

Superhost

Cabin in Prestonsburg

4.86 out of 5 average rating, 63 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

21 – 28 July

$2,348 AUD total

Superhost

Home in Elkhorn City

4.84 out of 5 average rating, 195 reviews

The Alma Potter House

Family friendly, small fenced in area. Two bedrooms/bath upstairs, 2 bedrooms/bath downstairs. large living/dining room. Rural, white water rafting, near Breaks Interstate Park, Pine Mountain Trail, Hillbilly Days, Hatfields & McCoys. Be in Norton/Wise, Grundy, VA, Pikeville, KY or Williamson WV in minutes. FB pages: Breaks Interstate Park, City of Elkhorn City Events, Southern Gap Adventure Trails, Arts Collaborative Theatre Inc., Kentucky Whitewater Rafting. Pike Co Tourism webpage.

24 – 31 Jan

$885 AUD total

Guest favourite

Home in Prestonsburg

4.95 out of 5 average rating, 42 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.

27 Nov – 4 Dec

$1,503 AUD total

Guest favourite

Cabin in Hagerhill

4.98 out of 5 average rating, 86 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.

24 – 31 Dec

$3,042 AUD total

Guest favourite

Home in Raccoon

4.85 out of 5 average rating, 26 reviews

Canary Cottage, Cheerful 3-Bedroom Home

10 miles from downtown Pikeville and access to Pikeville Medical Center, U Pike and local shopping. Relax with the whole family at this peaceful place to stay. Covered front porch ready for you to spend some time outdoors. Longer stays are welcomed or your alternative to a hotel; a place to stay when you are visiting the area or travelling through. Hatfield McCoy historical sites close by. Welcome to the Canary Cottage!

22 – 29 May

$1,066 AUD total

Guest favourite

Apartment in Allen City

5.0 out of 5 average rating, 22 reviews

Train View

Quaint getaway in a peaceful setting offers a distant hillside view with an occasional train coming around the hill. This second story apartment has.. . Three bedrooms . Two bathrooms . Kitchen . Dining area . Living room . Wifi . Wash room with washer and dryer . Free parking Great location for traveling healthcare professionals or anyone interested in work in the nearby towns. No smoking or pets allowed.

18 – 25 Aug

$1,440 AUD total

Guest favourite

Holiday home in Prestonsburg

4.99 out of 5 average rating, 72 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.

27 Sept – 4 Oct

$1,401 AUD total

Guest favourite

Cabin in Wellington

4.94 out of 5 average rating, 112 reviews

Peaceful cabin near Cave run lake Gorge and trails

Come enjoy the beautiful Daniel Boone National Forest. Retreat to a peaceful one-acre haven surrounded by abundant natural beauty. Explore the wonders of Cave Run Lake, Sheltowee Trace Trails, Red River Gorge, Natural Bridge or discover the charm of Morehead, KY and much more!

20 – 27 Aug

$1,407 AUD total

Guest favourite

Cabin in Louisa

4.98 out of 5 average rating, 176 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.

26 Jan – 2 Feb

$1,212 AUD total

Guest favourite

Cabin in Louisa

4.95 out of 5 average rating, 155 reviews

Sacred Winds - Yatesville Lake Luxury Cabin Rental

Welcome to Sacred Winds, a secluded and luxurious private cabin rental by owner at Yatesville Lake State Park in Eastern Kentucky. Located in a secluded hillside this cabin is perfect for your fishing, golfing, family or just a romantic getaway.

28 Feb – 7 Mar

$2,274 AUD total