Castle In Hawaii - Vacation Rentals in Prestonsburg

Jenny Wiley State Resort Park From US $123
         

8.7 (70 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Prestonsburg

Over 45+ Luxury Places to Stay in or Near Prestonsburg
Holiday Inn Express and Suites Pikeville by IHG From US $1,365
         

8.9 (162 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Business Services
Luxury Estate nestled atop stunning mountaintop golf course! From US $624
         

The Canyon at Pond Creek From US $553
         

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New
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
New 3 Bdrm unit w/great location & ex. amenities From US $262
         

9.6 (21 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Eccentric Privy-Sleeps6. 2nd floor & outdoor deck From US $223
         

Brookshire Inn From US $220
         

8.0 (14 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Pleasant 2-bedroom condo with AC in charming Prestonsburg. From US $191
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Downtown Paintsville Vacation Rental! From US $184
         

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New
House
  • Parking
  • Accessibility
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Prestonsburg

Over 11+ Top-Rated Vacation Rentals with a Pool in or Near Prestonsburg
Hampton Inn Pikeville From US $135
         

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9.2 (232 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Pool
Comfort Suites Prestonsburg West From US $124
         

8.6 (714 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Landmark Hotel From US $102
         

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8.4 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Hotel & Suites Pikeville by IHG From US $145
         

The Landmark Hotel From US $178
         

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8.2 (158 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Days Inn by Wyndham Paintsville From US $80
         

7.6 (527 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Prestonsburg

Over 9+ Pet-Friendly Vacation Rentals in or Near Prestonsburg
Cozy Home in Heart of Prestonsburg From US $135
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Heart of the highlands From US $115
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Comfort Inn Pikeville From US $150
         

9.0 (41 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Wheelchair Accessible
Kentucky's Hideaway Estate From US $500
         

9.6 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Comfort Suites Prestonsburg West From US $132
         

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8.3 (196 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Quality Inn & Suites Prestonsburg next to Mountain Arts Center From US $100
         

Comfort Inn Pikeville From US $132
         

7.5 (29 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area

Wheelchair Accessible Vacation Homes in Prestonsburg

Over 6+ Wheelchair Accessible Vacation Homes in or Near Prestonsburg
Brookshire Inn From US $90
         

8.3 (62 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Hampton Inn Pikeville From US $164
         

9.4 (570 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Super 8 by Wyndham Prestonsburg From US $54
         

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6.4 (227 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Quality Inn & Suites Prestonsburg next to Mountain Arts Center From US $119
         

8.0 (367 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Brookshire Inn From US $102
         

8.0 (114 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Jenny Wiley State Resort Park From US $101
         

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8.6 (393 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Prestonsburg Vacation Rentals and Airbnb Places to Stay Under $200

Over 10+ Prestonsburg Vacation Rentals and Airbnb Places to Stay Under $200
Near Scenic Parks: Convenient Home in Prestonsburg From US $126
         

Near Scenic Parks Convenient Home in Prestonsburg From US $162
         

Daniel Boone Motor Inn From US $70
         

7.4 (403 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
New to the area? Stop by and see the most recent bachelor pad on the scene From US $133
         

2.0 (1 Review)
Apartment
  • Air Conditioner
  • Designated Smoking Area
  • Internet
Super 8 by Wyndham Prestonsburg From US $83
         

6.4 (532 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Gorgeous Carriage House near KYCOM - 30 day min From US $73
         

Private entire home Pikeville 6 min. drive from PMC From US $160
         

9.6 (11 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety

About Prestonsburg Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Castleinhawaii Prestonsburg, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Prestonsburg. Places to stay near Prestonsburg with prices averaging US $123 a night.

Castleinhawaii makes it easy and safe to find and compare vacation rentals in Prestonsburg with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Prestonsburg

Type Count
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Prestonsburg

Pro Tip: Castleinhawaii makes it easy to compare the best listings on Castleinhawaii homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Castleinhawaii homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Prestonsburg.

Weather in Prestonsburg

View the weather forecast for Prestonsburg before booking your Prestonsburg Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Complexes around Prestonsburg, KY


Prestonsburg Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Prestonsburg?

There are a lot of options in Prestonsburg. If you plan on staying in the Prestonsburg area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Prestonsburg:

Which vacation homes in Prestonsburg are best for families?

If you are looking for a family-friendly vacation home in Prestonsburg, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Prestonsburg:

How many vacation rentals are available in Prestonsburg?

Currently, the total number of properties listed in 2026 is over 1 in the Prestonsburg area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Prestonsburg.