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Wheelwright Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Wheelwright vacation rentals

A dining area with a marble table, black chairs, a potted plant, a window with a view of greenery, and a mounted TV.

1. Cozy studio on US 23 between Pikeville and Prestonsburg

Cozy studio on US 23 between Pikeville and Prestonsburg
Harold
9.4 out of 10, Exceptional, (3 reviews)
"Our host stayed in good contact and the place was very cute and felt super comfortable. We were very happy with our stay :)"
United States
Lacy S.
$138 nightly
The price is $152
Sep 30 - Oct 1
Total with taxes and fees
Cozy studio on US 23 between Pikeville and Prestonsburg
A wooden dining table with a woven placemat, a tray with a mug and a sign saying "STAY COZY," and a small sign that reads "let it."

2. Cozy Tiny Home Quiet 1/1 Close to Riding Trails

Cozy Tiny Home Quiet 1/1 Close to Riding Trails
Martin
9.6 out of 10, Exceptional, (14 reviews)
"We found it to be a very clean, cozy, and quiet get-away!"
United States
Kimberly H.
$138 nightly
The price is $152
Sep 28 - Sep 29
Total with taxes and fees
Cozy Tiny Home Quiet 1/1 Close to Riding Trails

3. 2 Bedroom Creekside Getaway Near the Hillbilly Trail System

2 Bedroom Creekside Getaway Near the Hillbilly Trail System
Jenkins
$207 nightly
The price is $230
Oct 27 - Oct 28
Total with taxes and fees
2 Bedroom Creekside Getaway Near the Hillbilly Trail System
A wooden porch with a red door, a bench with heart-shaped cutouts, and two pillows with floral designs.

4. Holler's End, at the "head of the holler" but just 4.5 miles from Whitesburg

Holler's End, at the "head of the holler" but just 4.5 miles from Whitesburg
whitesburg
10.0 out of 10, Exceptional, (5 reviews)
"Great place. Lotsa room & everything very nice clean. "
United States
Aaron G.
$203 nightly
The price is $224
Oct 5 - Oct 6
Total with taxes and fees
Holler's End, at the "head of the holler" but just 4.5 miles from Whitesburg
A wooden interior with a sofa, a blue armchair, and a potted plant.

5. Inspiration Station

Inspiration Station
Pikeville
9.2 out of 10, Wonderful, (9 reviews)
"Great place to stay for a solo outing or couples getaway. The road leading up to the property is pretty dicey, but the place itself was great and the host was fantastic!"
United States
John H.
$193 nightly
The price is $207
Oct 8 - Oct 9
Total with taxes and fees
Inspiration Station
A covered deck with a grill, two chairs, and a table.

6. Modern Escape

Modern Escape
Pikeville
9.8 out of 10, Exceptional, (9 reviews)
"Super nice place will stay again for sure. "
United States
Rosa M.
$153 nightly
The price is $164
Oct 4 - Oct 5
Total with taxes and fees
Modern Escape
A wooden interior with a kitchen, a sofa, a ceiling fan, and a sign reading 'Backwoods Bungalow'.

7. Backwoods Bungalow

Backwoods Bungalow
Pikeville
10.0 out of 10, Exceptional, (13 reviews)
"Worked out very nice for our stay. "
United States
Cole A.
$193 nightly
The price is $207
Oct 20 - Oct 21
Total with taxes and fees
Backwoods Bungalow
A hallway with a chandelier, a bench, and a reception desk.

8. Spacious 5-bedroom house in town-within walking distance to everything

Spacious 5-bedroom house in town-within walking distance to everything
Clintwood
9.0 out of 10, Wonderful, (2 reviews)
"We really enjoyed our stay here. Melinda was amazing. Quick to respond to any questions I had. The location was perfect as we were attending a graduation in Wise. Home was clean and large enough for my family. Fully stocked with linens, beds were very comfortable, kitchen had everything we needed. A bonus was the coffee shop right next store. If we ever pass through this area again we would definitely stay here. "
United States
Cheryl
$203 nightly
The price is $228
Oct 7 - Oct 8
Total with taxes and fees
Spacious 5-bedroom house in town-within walking distance to everything
A bathroom with a wooden vanity, a mirror with lights, a towel rack, and a patterned floor.

9. Cozy 1-bedroom studio in the beautiful town of Clintwood, Virginia.

Cozy 1-bedroom studio in the beautiful town of Clintwood, Virginia.
Clintwood
$140 nightly
The price is $157
Sep 28 - Sep 29
Total with taxes and fees
Cozy 1-bedroom studio in the beautiful town of Clintwood, Virginia.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wheelwright Hotel Reviews

The Landmark Hotel

The Landmark Hotel

8/10 Good
"Air conditioning had a mildew smell, other than that, great stay. Good location"
Kevin 1-night trip
Posted 16 hours ago
The Landmark Hotel

Find out more about Wheelwright

Everything you need to know about Wheelwright vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wheelwright vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wheelwright vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wheelwright vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wheelwright. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Wheelwright in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wheelwright rentals

At Expedia, we put the best Wheelwright vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wheelwright rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wheelwright vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wheelwright. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Wheelwright?

Yes, there are vacation rentals near the most popular attractions in Wheelwright, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Wheelwright has to offer?

Red Oak Cottage: Visitors like this Wheelwright vacation home rental. It is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

What’s there to see and do in Wheelwright?

While exploring the area, visit the sights like University of Pikeville, Appalachian Wireless Arena, and Big Sandy Heritage Center Museum. The Real McCoy Trailhead and Appalachian Center for the Arts are a couple of places you'll find in the larger area.

What’s a vacation rental in Wheelwright like?

Vacation rentals are privately owned properties where you can stay for several days or longer in Wheelwright. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.