A snow-covered highway curving through a mountainous landscape with a sunset sky. A road sign indicates the direction to Whitesburg and Harlan.

Letcher County Vacation Rentals

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Our top choices for Letcher County vacation rentals

A wooden porch with a red door, a bench with heart-shaped cutouts, and two pillows with floral designs.

1. 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.
The price is CA $154
CA $326 total
includes taxes & fees
Oct 20 - Oct 21
Holler's End, at the "head of the holler" but just 4.5 miles from Whitesburg
A shower curtain with a plant and cat design.

2. Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.

Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
Partridge
9.6 out of 10, Exceptional, (13 reviews)
"Host is the BEST!"
United States
Melissa L.
The price is CA $154
CA $202 total
includes taxes & fees
Oct 18 - Oct 19
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
A covered outdoor area with wooden flooring, a wooden fence, and several Adirondack chairs.

3. Coal Town Gem

Coal Town Gem
Haysi
9.6 out of 10, Exceptional, (31 reviews)
"Enjoyed our stay in the small town of Haysi. It gave us easy access to the Breaks Interstate Park. We also enjoyed visiting the gift shop located below the VRBO."
United States
Bob T.
The price is CA $161
CA $209 total
includes taxes & fees
Oct 14 - Oct 15
Coal Town Gem
A two-story house with a porch decorated with red, white, and blue accents.

4. Nottingham Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St

Nottingham Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St
Wise
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful accommodations, and the hosts were absolutely fabulous! "
United States
Dan B.
The price is CA $207
CA $262 total
includes taxes & fees
Oct 20 - Oct 21
Nottingham Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St
A house with a covered porch and a staircase leading to the entrance.

5. Charming 2-bedroom house in Wise, Virginia

Charming 2-bedroom house in Wise, Virginia
Wise
10.0 out of 10, Exceptional, (15 reviews)
"Such a beautiful place with so many special touches. We love being here and enjoying Wise County. The host creates a beautiful and comfortable space."
United States
Chasity F.
The price is CA $171
CA $302 total
includes taxes & fees
Oct 14 - Oct 15
Charming 2-bedroom house in Wise, Virginia
A covered porch with white railings, a brick wall, and a view of a forested area.

6. Breaks Home: 3 Mi to ATV Trails!

Breaks Home: 3 Mi to ATV Trails!
3.0 star property
Breaks
The price is CA $197
CA $733 total
includes taxes & fees
Oct 14 - Oct 15
Breaks Home: 3 Mi to ATV Trails!
A cozy living room with a fireplace, a black leather sofa, a TV, and a wooden floor.

7. Beautiful Loft in the Woods

Beautiful Loft in the Woods
Harlan
10.0 out of 10, Exceptional, (7 reviews)
"Melody was very friendly and welcoming! The Loft was beautiful, immaculate, cozy and a wonderful place to stay! 100% positive review!"
United States
James
The price is CA $193
CA $397 total
includes taxes & fees
Oct 14 - Oct 15
Beautiful Loft in the Woods
A living room with a wooden floor, a ceiling fan, a sofa, a chair, and a wall-mounted sign.

8. Nan’s Porch - 2 Bedroom home with outdoor firepit

Nan’s Porch - 2 Bedroom home with outdoor firepit
Cumberland
The price is CA $187
CA $449 total
includes taxes & fees
Oct 18 - Oct 19
Nan’s Porch - 2 Bedroom home with outdoor firepit
A bedroom with a bed, a wooden nightstand, a chair, a door, and a view of the outside.

9. Dan’s Den - Two-bedroom home with hot tub, fire pit, and dog park

Dan’s Den - Two-bedroom home with hot tub, fire pit, and dog park
Cumberland
The price is CA $238
CA $496 total
includes taxes & fees
Oct 22 - Oct 23
Dan’s Den - Two-bedroom home with hot tub, fire pit, and dog park
Interior

10. 2 Bedroom Creekside Getaway Near the Hillbilly Trail System

2 Bedroom Creekside Getaway Near the Hillbilly Trail System
Jenkins
The price is CA $195
CA $340 total
includes taxes & fees
Oct 27 - Oct 28
2 Bedroom Creekside Getaway Near the Hillbilly Trail System
A wooden deck with two plastic chairs and a view of a grassy area with trees.

11. The 100 Acre Woods located in the Appalachian mountains Clintwood Va

The 100 Acre Woods located in the Appalachian mountains Clintwood Va
Clintwood
10.0 out of 10, Exceptional, (5 reviews)
"Stay was great everything was satisfactory. Great host"
United States
Ernest C.
The price is CA $161
CA $298 total
includes taxes & fees
Oct 14 - Oct 15
The 100 Acre Woods located in the Appalachian mountains Clintwood Va
A hallway with a chandelier, a bench, and a reception desk.

12. 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
The price is CA $153
CA $337 total
includes taxes & fees
Oct 14 - Oct 15
Spacious 5-bedroom house in town-within walking distance to everything
A covered outdoor seating area with wicker furniture, a glass table, and a blue kayak.

13. The Lofts at Three Rivers

The Lofts at Three Rivers
Haysi
10.0 out of 10, Exceptional, (17 reviews)
"Great experience, would stay again 100% "
United States
Amanda C.
The price is CA $321
CA $538 total
includes taxes & fees
Oct 22 - Oct 23
The Lofts at Three Rivers
A covered porch with white railings, a brick wall, and a view of a forested area.

14. Breaks Home: 3 Mi to ATV Trails!

Breaks Home: 3 Mi to ATV Trails!
Breaks
10.0 out of 10, Exceptional, (7 reviews)
"Loved this place. Its very well appointed and my kids enjoyed playing in the creek. My favorite was the front porch. Very comfortable and the property managers were very responsive."
United States
Leah G.
The price is CA $141
CA $751 total
includes taxes & fees
Oct 14 - Oct 15
Breaks Home: 3 Mi to ATV Trails!
A bedroom with a wooden bed, a dresser, a mirror, and a painting on the wall.

15. Historic Cottage Near PMC, UPIKE and Arena

Historic Cottage Near PMC, UPIKE and Arena
Pikeville
The price is CA $204
CA $356 total
includes taxes & fees
Oct 20 - Oct 21
Historic Cottage Near PMC, UPIKE and Arena
A covered porch with white columns, outdoor furniture, and potted plants.

16. Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath

Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
Wise
10.0 out of 10, Exceptional, (13 reviews)
"Very comfortable stay! "
United States
Chasity F.
The price is CA $178
CA $230 total
includes taxes & fees
Oct 18 - Oct 19
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
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 Letcher County Hotel Reviews

The Inn at Wise

The Inn at Wise

8/10 Good
"Did not like the breakfast available."
Debra 2-night trip
Posted 3 hours ago
The Inn at Wise

Find out more about Letcher County

Everything you need to know about Letcher County 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 Letcher County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... 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 Letcher County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Letcher County vacation rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Letcher County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Letcher County vacation rentals we have selected for you start as low as CA $202 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Letcher County rentals

At Expedia, we put the best Letcher County 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 Letcher County 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 Letcher County 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 Letcher County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.