Cumberland Gap Holiday Rentals

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Cumberland Gap holiday rentals

Exterior
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cottage in Cumberland Gap

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
9.2 out of 10, Wonderful, (42)
"Great location. Easy walk to town and close to hiking areas. Highly recommend. "
United States
Linda O.
The price is HK$770
HK$1,635 total
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Exterior
Luxury Brooklyn St APT - Near LMU & Nat’l Park

Apartment in Cumberland Gap

Luxury Brooklyn St APT - Near LMU & Nat’l Park
9.6 out of 10, Exceptional, (25)
"This apartment was perfect for my husband and I and 2 adult children. It was right downtown Cumberland Gap with great views and a cute patio to enjoy morning coffee. It had everything we needed and was extremely clean. The hosts was easy to communicate with and provided all the information we needed to enjoy our stay. "
United States
kim s.
Luxury Brooklyn St APT - Near LMU & Nat’l Park
Interior
Peaceful & Private! Pet-friendly Williamsburg Home

Cottage in Williamsburg

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
The price is HK$762
HK$2,387 total
includes taxes & fees
25 Dec - 26 Dec
Peaceful & Private! Pet-friendly Williamsburg Home
TV, fireplace
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Cabin in Tazewell

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
10.0 out of 10, Exceptional, (4)
"Everything was clean and felt like home.host was really nice and I will definitely be staying again."
United States
Nicholas H.
The price is HK$672
HK$1,259 total
includes taxes & fees
5 Jan - 6 Jan 2026
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Terrace/patio
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Holiday Home in Speedwell

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
9.4 out of 10, Exceptional, (19)
"It was exceptional "
United States
Dennis W.
The price is HK$560
HK$1,240 total
includes taxes & fees
28 Dec - 29 Dec
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Interior
One Bedroom Rustic Cabin

Cabin in Speedwell

One Bedroom Rustic Cabin
2.0 star property
The price is HK$305
HK$672 total
includes taxes & fees
28 Dec - 29 Dec
One Bedroom Rustic Cabin
Fridge, microwave, oven, stovetop
Harrogate Home Mountain View’s Dog Friendly

Holiday Home in Harrogate

Harrogate Home Mountain View’s Dog Friendly
10.0 out of 10, Exceptional, (22)
"Great location with friendly neighbors!"
United States
Evan C.
The price is HK$1,225
HK$2,290 total
includes taxes & fees
27 Dec - 28 Dec
Harrogate Home Mountain View’s Dog Friendly
Miscellaneous
RV/Camper Sites. No Electric

Camping in Speedwell

RV/Camper Sites. No Electric
2.0 star property
The price is HK$218
HK$487 total
includes taxes & fees
25 Dec - 26 Dec
RV/Camper Sites. No Electric
WiFi, bed sheets
Modern 20’ Travel Trailer with bunks and a queen bed

Mobile Home in Speedwell

Modern 20’ Travel Trailer with bunks and a queen bed
2.0 star property
The price is HK$467
HK$933 total
includes taxes & fees
25 Dec - 26 Dec
Modern 20’ Travel Trailer with bunks and a queen bed
2 bedrooms, iron/ironing board, free WiFi, bed sheets
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

Holiday Home in Middlesboro

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
10.0 out of 10, Exceptional, (22)
"Great property! Very clean and homey!"
United States
Lillian I.
The price is HK$926
HK$1,809 total
includes taxes & fees
28 Dec - 29 Dec
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Property grounds
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Holiday Home in Pineville

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
10.0 out of 10, Exceptional, (2)
"We stayed here for a wedding weekend in Pineville, KY, and it was absolutely perfect from start to finish. The home was spotless, cozy, and had everything we could possibly need. The beds were so comfortable, and we instantly felt at home the moment we walked in.What truly set this stay apart was the host’s kindness and above-and-beyond hospitality. We got lost in the middle of the night trying to find the property, and the host stayed on the phone with us, patiently guiding us right to the...
United States
Samantha P.
The price is HK$1,239
HK$2,300 total
includes taxes & fees
29 Dec - 30 Dec
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Terrace/patio
Peaceful & Private! Pet-Friendly Williamsburg Home

Holiday Home in Williamsburg

Peaceful & Private! Pet-Friendly Williamsburg Home
2.0 star property
The price is HK$684
HK$2,346 total
includes taxes & fees
25 Dec - 26 Dec
Peaceful & Private! Pet-Friendly Williamsburg Home
Outdoor spa tub
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

Villa in Sharps Chapel

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
10.0 out of 10, Exceptional, (5)
"This was definitely the most romantic VRBO we’ve stayed at!!! Very clean, and the view from all of the balconies was incredible!!! "
United States
Stan N.
The price is HK$1,155
HK$2,372 total
includes taxes & fees
6 Jan - 7 Jan 2026
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
Fridge, microwave, oven, stovetop
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell

Holiday Home in Tazewell

Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
2.0 star property
10.0 out of 10, Exceptional, (7)
"Great place that is well stocked and close to amenities as well. Spacious house with an awesome porch with a view!"
United States
Brendan W.
The price is HK$1,548
HK$3,397 total
includes taxes & fees
27 Dec - 28 Dec
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
Fridge, microwave, oven, stovetop
Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock

Cabin in Rock Harbor

Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock
2.0 star property
The price is HK$972
HK$3,716 total
includes taxes & fees
7 Jan - 8 Jan 2026
Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock
3 bedrooms, desk, iron/ironing board, travel cot
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Holiday Home in Middlesboro

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is HK$1,361
HK$2,889 total
includes taxes & fees
29 Dec - 30 Dec
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Living area
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

Holiday Home in Pineville

Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
10.0 out of 10, Exceptional, (1)
"Well cared for property with nice upgrades! Perfect for our stay, everything we needed, and accommodating. "
United States
Hope C.
The price is HK$1,470
HK$2,100 total
includes taxes & fees
7 Jan - 8 Jan 2026
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
Exterior detail
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

Cottage in Pineville

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
9.0 out of 10, Wonderful, (2)
"The home was just perfect for what we needed. Looking forward to seeing how it comes out when all construction is finished! Host was very responsive. Will stay again"
United States
Kami L.
The price is HK$1,386
HK$2,232 total
includes taxes & fees
6 Jan - 7 Jan 2026
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
Interior
Spacious Lakefront Home, Sleeps 8・Dock・Pool Table

Cabin in Sharps Chapel

Spacious Lakefront Home, Sleeps 8・Dock・Pool Table
2.0 star property
The price is HK$1,081
HK$4,337 total
includes taxes & fees
7 Jan - 8 Jan 2026
Spacious Lakefront Home, Sleeps 8・Dock・Pool Table
Terrace/patio
Lakefront House, Sleeps 12・Hot Tub・Mtn view・Grill

Holiday Home in New Tazewell

Lakefront House, Sleeps 12・Hot Tub・Mtn view・Grill
2.0 star property
The price is HK$1,089
HK$4,286 total
includes taxes & fees
26 Dec - 27 Dec
Lakefront House, Sleeps 12・Hot Tub・Mtn view・Grill
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 Cumberland Gap Hotel Reviews

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

10/10 Excellent
"Great staff, clean room, upgraded room, recently renovated room, nice Mountain View. "
Ashley 1-night trip
Posted 3 days ago
Days Inn by Wyndham Jellico - Tennessee State Line

Find out more about Cumberland Gap

Search for holiday rentals in Cumberland Gap on Expedia! You can easily find your home rentals, villas, holiday apartments in Cumberland Gap using one of the methods below:

  • View our selection of featured holiday rentals in Cumberland Gap
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  • Enter your travel dates to view the best deals on holiday rentals in Cumberland Gap while they last

Look no further and take a look at our great range of rental properties in Cumberland Gap!

Frequently asked questions

Are there holiday rentals in Cumberland Gap?

Yes, there are holiday rentals close to the most popular sights in Cumberland Gap, or you can select a more secluded option if you're looking for a relaxing stay. Cumberland Gap is known for its riverfront and mountain views. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that Cumberland Gap has to offer?

Norris Lake Home with Heated Saltwater Pool and Hot Tub in Deerfield: This holiday home rental outside of Cumberland Gap is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a patio and 1 hot tub.

What can I see and do in Cumberland Gap?

Explore the area and family-friendly sights such as New Tazewell Municipal Park, or get out into nature at a spot like The Pinnacle. Cumberland Gap National Historical Park and Lincoln Memorial University are a couple of places you'll find in the wider area.

What are holiday rentals like in Cumberland Gap?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cumberland Gap. Holiday rentals feature extras like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.