Historical Hotels in Eastern Kentucky, KY
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Featured Eastern Kentucky Historic Hotels

The Olde Mill Inn Bed & Breakfast
603 Pennlyn Avenue Cumberland Gap TN
$149 nightly
The price is $169 total per night
$169 total
Jan 15 - Jan 16, 2026
Total with taxes and fees
Guests of The Olde Mill Inn Bed & Breakfast enjoy free WiFi in public areas, conference space, and a terrace. There's free parking if you drive. Multilingual staff is on hand to answer questions. This smoke-free bed & breakfast also has wedding services.
Breakfast included
Parking included

Climb On Inn-RRG- 3BD & 2BA - Outdoor Adventure Paradise- Pet Friendly -Cozy
Pine Ridge KY
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer

Cumberland Falls State Resort Park
7351 Hwy. 90 Williamsburg KY
Guests of Cumberland Falls State Resort Park enjoy a children's pool, free WiFi in public areas, and meeting rooms. If you decide to drive, there's free parking. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Other amenities at this family-friendly hotel include a seasonal outdoor pool, a microwave in a common area, and a terrace.
Pool
Pet friendly

Cumberland Gap Inn
630 Brooklyn Street Cumberland Gap TN
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $111 total per night
$111 total
Dec 27 - Dec 28
Total with taxes and fees
Guests staying at Cumberland Gap Inn enjoy free WiFi in public areas, a terrace, and a vending machine. A stay here includes free parking. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. This motel also has barbecue grills.
Pet friendly
Parking included

Hampton Inn Pikeville
831 Hambley Blvd Pikeville KY
Free Cancellation
Reserve now, pay when you stay
$146 nightly
The price is $167 total per night
$167 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Hampton Inn Pikeville features a gym, free WiFi in public areas, and conference space. If you drive, take advantage of free parking. Front-desk staff can answer questions 24/7, and assist with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a business center, free newspapers, and laundry facilities.
Breakfast included
Pet friendly

Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
Free Cancellation
$111 nightly
The price is $123 total per night
$123 total
Dec 28 - Dec 29
Total with taxes and fees
At Holiday Inn Express Middlesboro by IHG, guests enjoy an outdoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. Front-desk staff can answer questions 24/7, and assist with luggage storage, dry cleaning/laundry, and securing valuables. Additional amenities include conference space, a 24-hour business center, and free newspapers.
Pool
Breakfast included

Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Free Cancellation
$94 nightly
The price is $103 total per night
$103 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
At Sleep Inn & Suites Middlesboro, guests have access to a gym, free WiFi in public areas, and a 24-hour business center. If you plan to drive, free parking is available. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. Additional amenities include a computer station, free newspapers, and laundry facilities.
Breakfast included
Pet friendly

Econo Lodge Middlesboro
1623 Cumberland Avenue Middlesboro KY
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $98 total per night
$98 total
Dec 28 - Dec 29
Total with taxes and fees
At Econo Lodge Middlesboro, guests have access to free WiFi in public areas, a seasonal outdoor pool, and laundry facilities. If you decide to drive, there's free parking. The 24-hour front desk has staff always at the ready. Additional amenities include a vending machine and a TV in a common area.
Pool
Breakfast included

Quality Inn & Suites Prestonsburg next to Mountain Arts Center
85 Hal Rogers Drive Prestonsburg KY
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $119 total per night
$119 total
Dec 27 - Dec 28
Total with taxes and fees
Quality Inn & Suites Prestonsburg next to Mountain Arts Center features a 24-hour gym, free WiFi in public areas, and a business center. There's free parking if you drive. The 24-hour front desk has staff always at the ready. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a meeting room, laundry facilities, and a TV in a common area.
Breakfast included
Pet friendly

Comfort Suites Prestonsburg West
51 Hal Rogers Dr Prestonsburg KY
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $115 total per night
$115 total
Dec 28 - Dec 29
Total with taxes and fees
At Comfort Suites Prestonsburg West, guests enjoy an indoor pool, a gym, and free WiFi in public areas. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready. Additional amenities include a business center, a meeting room, and a computer station.
Pool
Breakfast included

Super 8 by Wyndham Prestonsburg
80 Shoppers Path Prestonsburg KY
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $74 total per night
$74 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
Super 8 by Wyndham Prestonsburg features free WiFi in public areas, a business center, and free newspapers. Free parking is available if you drive. The 24-hour front desk has staff always at the ready. This hotel also has a vending machine.
Breakfast included
Pet friendly

Jenny Wiley State Resort Park
75 Theatre Ct Prestonsburg KY
Jenny Wiley State Resort Park features a marina, meeting rooms, and a seasonal outdoor pool. There's free parking if you drive. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a fireplace in the lobby, a vending machine, and barbecue grills.
Pool
Pet friendly

Ramada Hotel & Conference Center by Wyndham Paintsville
624 James Trimble Blvd Paintsville KY
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $119 total per night
$119 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ramada Hotel & Conference Center by Wyndham Paintsville features an indoor pool, an outdoor pool, and a 24-hour gym. Free parking is included with your stay. Front-desk staff can answer questions 24/7, and assist with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include free WiFi in public areas, a hot tub, and conference space.
Pool
Hot Tub

Days Inn by Wyndham Paintsville
512 S Mayo Trail Paintsville KY
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $75 total per night
$75 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
Days Inn by Wyndham Paintsville features an outdoor pool, free WiFi in public areas, and a business center. If you plan to drive, free parking is available. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a seasonal outdoor pool, free newspapers, and laundry facilities.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Eastern Kentucky
View all propertiesLowest 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.
Eastern Kentucky hotels essential information
Accommodation | 842 hotels |
|---|---|
Lowest Price | $74 |
Highest Price | $169 |
Popular hotels | The Olde Mill Inn Bed & Breakfast, Climb On Inn-RRG- 3BD & 2BA - Outdoor Adventure Paradise- Pet Friendly -Cozy , Cumberland Falls State Resort Park, Cumberland Gap Inn, Hampton Inn Pikeville, Holiday Inn Express Middlesboro by IHG, Sleep Inn & Suites Middlesboro, Econo Lodge Middlesboro, Quality Inn & Suites Prestonsburg next to Mountain Arts Center, Comfort Suites Prestonsburg West, Super 8 by Wyndham Prestonsburg, Jenny Wiley State Resort Park, Ramada Hotel & Conference Center by Wyndham Paintsville, Days Inn by Wyndham Paintsville |
Recent Historic Hotels Reviews

Baymont by Wyndham London KY
5/5 Excellent
"Friendly staff and nice room"
A verified traveler stayed at Baymont by Wyndham London KY
Posted 4 days ago
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