Cumberland Gap Holiday Rentals

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Check prices for these dates

Tonight
21 Dec - 22 Dec
Tomorrow
22 Dec - 23 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Our top choices for Cumberland Gap holiday rentals

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

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
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$1,652 total
includes taxes & fees
22 Dec - 23 Dec
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Exterior
Luxury Brooklyn St APT - Near LMU & Nat’l Park

Luxury Brooklyn St APT - Near LMU & Nat’l Park

Luxury Brooklyn St APT - Near LMU & Nat’l Park
Cumberland Gap
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.
The price is HK$786
HK$1,573 total
includes taxes & fees
22 Dec - 23 Dec
Luxury Brooklyn St APT - Near LMU & Nat’l Park
Interior
Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is HK$763
HK$2,388 total
includes taxes & fees
22 Dec - 23 Dec
Peaceful & Private! Pet-friendly Williamsburg Home
TV, fireplace
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Tazewell
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$714
HK$1,307 total
includes taxes & fees
22 Dec - 23 Dec
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

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Speedwell
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
23 Dec - 24 Dec
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Interior
One Bedroom Rustic Cabin

One Bedroom Rustic Cabin

One Bedroom Rustic Cabin
2.0 star property
Speedwell
The price is HK$305
HK$673 total
includes taxes & fees
22 Dec - 23 Dec
One Bedroom Rustic Cabin
Fridge, microwave, oven, stovetop
Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (22)
"Great location with friendly neighbors!"
United States
Evan C.
The price is HK$1,226
HK$2,337 total
includes taxes & fees
27 Dec - 28 Dec
Harrogate Home Mountain View’s Dog Friendly
Miscellaneous
RV/Camper Sites. No Electric

RV/Camper Sites. No Electric

RV/Camper Sites. No Electric
2.0 star property
Speedwell
The price is HK$224
HK$494 total
includes taxes & fees
22 Dec - 23 Dec
RV/Camper Sites. No Electric
WiFi, bed sheets
Modern 20’ Travel Trailer with bunks and a queen bed

Modern 20’ Travel Trailer with bunks and a queen bed

Modern 20’ Travel Trailer with bunks and a queen bed
2.0 star property
Speedwell
The price is HK$459
HK$924 total
includes taxes & fees
22 Dec - 23 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,

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Middlesboro
10.0 out of 10, Exceptional, (22)
"Great property! Very clean and homey!"
United States
Lillian I.
The price is HK$926
HK$1,810 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

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Pineville
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$1,240
HK$2,301 total
includes taxes & fees
22 Dec - 23 Dec
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Terrace/patio
Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
2.0 star property
Williamsburg
The price is HK$685
HK$2,365 total
includes taxes & fees
22 Dec - 23 Dec
Peaceful & Private! Pet-Friendly Williamsburg Home
Outdoor spa tub
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
Sharps Chapel
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$1,214
HK$2,533 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

Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell

Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
2.0 star property
Tazewell
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$3,398 total
includes taxes & fees
22 Dec - 23 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

Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock

Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock
2.0 star property
Rock Harbor
The price is HK$973
HK$3,717 total
includes taxes & fees
5 Jan - 6 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.

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Middlesboro
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is HK$1,362
HK$2,891 total
includes taxes & fees
23 Dec - 24 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

Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
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$1,471
HK$2,102 total
includes taxes & fees
22 Dec - 23 Dec
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!

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
Pineville
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$1,276
HK$2,102 total
includes taxes & fees
21 Jan - 22 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

Spacious Lakefront Home, Sleeps 8・Dock・Pool Table

Spacious Lakefront Home, Sleeps 8・Dock・Pool Table
2.0 star property
Sharps Chapel
The price is HK$1,082
HK$4,324 total
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious Lakefront Home, Sleeps 8・Dock・Pool Table
Terrace/patio
Lakefront House, Sleeps 12・Hot Tub・Mtn view・Grill

Lakefront House, Sleeps 12・Hot Tub・Mtn view・Grill

Lakefront House, Sleeps 12・Hot Tub・Mtn view・Grill
2.0 star property
New Tazewell
The price is HK$1,089
HK$4,288 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

Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

10/10 Excellent
"Every December our family rents a cabin for a long weekend to be together. Family affair was the best we’ve ever picked. The house is well-built, well-stocked and very clean. Since it’s winter, we did not enjoy the lake, but I can only imagine the additional fun on the water!"
Christi S. 3-night trip
Posted 3 days ago
Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

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:

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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.