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 Holiday Rentals

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Our top choices for Letcher County holiday 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 NZ$400
includes taxes & fees
19 Oct - 20 Oct
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)
The price is NZ$252
includes taxes & fees
11 Oct - 12 Oct
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 NZ$261
includes taxes & fees
13 Oct - 14 Oct
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 NZ$298
includes taxes & fees
19 Oct - 20 Oct
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, (14 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 NZ$374
includes taxes & fees
11 Oct - 12 Oct
Charming 2-bedroom house in Wise, Virginia
A cozy living room with a fireplace, a black leather sofa, a TV, and a wooden floor.

6. Beautiful Loft in the Woods

Beautiful Loft in the Woods
Harlan
10.0 out of 10, Exceptional, (6 reviews)
"Very comfortable, modern and spacious."
United States
Kellie
The price is NZ$486
includes taxes & fees
11 Oct - 12 Oct
Beautiful Loft in the Woods
A bedroom with a bed, a wooden nightstand, a chair, a door, and a view of the outside.

7. Dan’s Den - Two bedroom home with outdoor firepit

Dan’s Den - Two bedroom home with outdoor firepit
Cumberland
The price is NZ$612
includes taxes & fees
23 Oct - 24 Oct
Dan’s Den - Two bedroom home with outdoor firepit
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 NZ$542
includes taxes & fees
18 Oct - 19 Oct
Nan’s Porch - 2 Bedroom home with outdoor firepit
Interior

9. 2 Bedroom Creekside Getaway Near the Hillbilly Trail System

2 Bedroom Creekside Getaway Near the Hillbilly Trail System
Jenkins
The price is NZ$413
includes taxes & fees
27 Oct - 28 Oct
2 Bedroom Creekside Getaway Near the Hillbilly Trail System
A hallway with a chandelier, a bench, and a reception desk.

10. 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 NZ$407
includes taxes & fees
12 Oct - 13 Oct
Spacious 5-bedroom house in town-within walking distance to everything
A covered porch with white railings, a brick wall, and a view of a forested area.

11. Breaks Home: 3 Mi to ATV Trails!

Breaks Home: 3 Mi to ATV Trails!
3.0 star property
Breaks
The price is NZ$916
includes taxes & fees
14 Oct - 15 Oct
Breaks Home: 3 Mi to ATV Trails!
A covered porch with white railings, a brick wall, and a view of a forested area.

12. 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 NZ$923
includes taxes & fees
14 Oct - 15 Oct
Breaks Home: 3 Mi to ATV Trails!
A covered porch with white columns, outdoor furniture, and potted plants.

13. 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)
The price is NZ$268
includes taxes & fees
18 Oct - 19 Oct
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
A covered outdoor seating area with wicker furniture, a glass table, and a blue kayak.

14. 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 NZ$648
includes taxes & fees
12 Oct - 13 Oct
The Lofts at Three Rivers
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

Gateway To The Breaks Motel

Gateway To The Breaks Motel

10/10 Excellent
"WA"
Andrea 1-night trip
Posted 10 hours ago
Gateway To The Breaks Motel

Find out more about Letcher County

Everything you need to know about Letcher County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Letcher County holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Letcher County holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Letcher County holiday rentals we have selected for you start as low as NZ$252 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 holiday 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 holiday.

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.