Pilgrim Holiday Rentals

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Holiday Rentals in Pilgrim

Rustic Retreat at Backwoods Bungalow – Secluded Cabin with Modern Comforts
2.0 star property
10.0 out of 10, Exceptional, (8)
"We absolutely enjoyed our visit and love this beautiful cabin. It was a very relaxing comfortable stay. We already booked it again for our next visit in September. The host, Josh, was awesome! Can’t wait to return! "
United States
L.K.
The price is AU$212
includes taxes & fees
3 Nov - 4 Nov
Rustic Retreat at Backwoods Bungalow – Secluded Cabin with Modern Comforts
Cozy Tiny Home Quiet 1/1 Close to Riding Trails
9.6 out of 10, Exceptional, (5)
"Very nice places. Clean and cute. Love the surrounding Mountain View’s. Definitely on my list to stay again."
United States
Kevin S.
The price is AU$236
includes taxes & fees
21 Oct - 22 Oct
Cozy Tiny Home Quiet 1/1 Close to Riding Trails
Walking distance to gas station/riding passes, and the famous Sherry Bo’s diner
9.8 out of 10, Exceptional, (6)
"House was listed accurately, it was just what we needed for our stay to go on the trails.Easy check in and close to everything."
United States
Heather M.
The price is AU$292
includes taxes & fees
21 Oct - 22 Oct
Walking distance to gas station/riding passes, and the famous Sherry Bo’s diner
Tiny Home on Wheels: Your Modern Escape Awaits"
2.0 star property
10.0 out of 10, Exceptional, (6)
"Had a great time at this little mountain getaway, would absolutely come back!"
United States
Dakota C.
The price is AU$191
includes taxes & fees
3 Nov - 4 Nov
Tiny Home on Wheels: Your Modern Escape Awaits"
Cozy studio on US 23 between Pikeville and Prestonsburg
2.0 star property
10.0 out of 10, Exceptional, (1)
"I have no complaints. The property was nice and comfortable. It was clean. The property manager was very easy to get ahold of and extremely. Would stay her again. "
United States
Zach S.
The price is AU$236
includes taxes & fees
27 Oct - 28 Oct
Cozy studio on US 23 between Pikeville and Prestonsburg
Appalachian Hideaways Cabin #2
9.6 out of 10, Exceptional, (11)
"Nice little spot to stay after a day riding the trails."
United States
Curtis J.
The price is AU$312
includes taxes & fees
21 Oct - 22 Oct
Appalachian Hideaways Cabin #2
Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature
2.0 star property
8.4 out of 10, Very good, (5)
"Great place to stay, nice new buildings. Owner is super easy to communicate with. Highly recommended!!!!👍"
United States
Lyle G.
The price is AU$228
includes taxes & fees
3 Nov - 4 Nov
Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature
Cozy Home in Heart of Prestonsburg
10.0 out of 10, Exceptional, (8)
"We loved our stay at The Shotgun House! It was very clean, peaceful and safe. The bed was super comfortable, and we lacked for nothing as the host has the place fully stocked. Super easy check-in and out process. The location is perfect! You’re in town and within minutes of food, shopping and local entertainment. We will definitely stay again soon. "
United States
Tracey N.
The price is AU$273
includes taxes & fees
27 Oct - 28 Oct
Cozy Home in Heart of Prestonsburg
Papa Bear's Den!! “The perfect location to visit the trails”
10.0 out of 10, Exceptional, (11)
"Very clean. Close to trails. Can't beat the price or location. Forgot something? Don't worry, this place has it, just in case. I'm sure we will rent again. "
United States
Sonia W.
The price is AU$322
includes taxes & fees
3 Nov - 4 Nov
Papa Bear's Den!! “The perfect location to visit the trails”
Mama Bears den “The perfect location to visit the Hatfield and McCoy trails”
10.0 out of 10, Exceptional, (7)
"We throughly enjoyed our stay. Gary is an excellent host. We’ll definitely stay again when we are in the area. "
United States
Jessica R.
The price is AU$322
includes taxes & fees
2 Nov - 3 Nov
Mama Bears den “The perfect location to visit the Hatfield and McCoy trails”
5th Wheel RV On Permanent Site ,Near Hatfield McCoy Sites
9.0 out of 10, Wonderful, (2)
"Very pet friendly. Excellent hosts. "
United States
Joyce V.
The price is AU$248
includes taxes & fees
26 Oct - 27 Oct
5th Wheel RV On Permanent Site ,Near Hatfield McCoy Sites
Cozy Creekside Tiny Home w/ Full Kitchen - Walk to Distillery
The price is AU$253
includes taxes & fees
27 Oct - 28 Oct
Cozy Creekside Tiny Home w/ Full Kitchen - Walk to Distillery
Sheppard's Holler: Your WV Adventure Home
10.0 out of 10, Exceptional, (5)
"It was a great place to stay, quiet and peaceful. The lake was right up the road and the whole house just felt like home. The owners were very nice and helpful. Anytime I needed something they were there to answer any questions I had. Would definitely stay there again!"
United States
Christy
The price is AU$406
includes taxes & fees
2 Nov - 3 Nov
Sheppard's Holler: Your WV Adventure Home
Creekside Retreat, 3 bedroom, Large parking, Picnic area. Across from Trail 14
9.8 out of 10, Exceptional, (39)
"Very clean, had all of the amenities you would need, plenty of parking space, will definitely stay again"
United States
Brian L.
The price is AU$400
includes taxes & fees
27 Oct - 28 Oct
Creekside Retreat, 3 bedroom, Large parking, Picnic area. Across from Trail 14
Suite 3 South Williamson, Ky HMT 10
10.0 out of 10, Exceptional, (2)
"Location was great for our needs. Nice accomodations"
United States
Anonymous traveller
Suite 3 South Williamson, Ky HMT 10
Charming 2-bedroom cabin uwith WiFi, AC in amazing McCarr
10.0 out of 10, Exceptional, (3)
"Lovely place to stay and close to the trails. Kids loved the dock to fish off of. "
United States
BOBBIE D.
The price is AU$395
includes taxes & fees
21 Oct - 22 Oct
Charming 2-bedroom cabin uwith WiFi, AC in amazing McCarr
RV Site 14 Camper - Hatfield McCoy Trails
The price is AU$342
includes taxes & fees
22 Oct - 23 Oct
RV Site 14 Camper - Hatfield McCoy Trails
Cheerful Three Bedroom Residential Home
The price is AU$586
includes taxes & fees
21 Oct - 22 Oct
Cheerful Three Bedroom Residential Home
*The Decked out Den*
10.0 out of 10, Exceptional, (15)
"House was great, very clean, exactly as advertised, close and easy access to trails and dining. Will stay again. "
United States
Larry H.
The price is AU$577
includes taxes & fees
2 Nov - 3 Nov
*The Decked out Den*
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
9.8 out of 10, Exceptional, (7)
"Loved the house had a great experience would definitely stay again"
United Kingdom
Gregory S.
The price is AU$459
includes taxes & fees
12 Nov - 13 Nov
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
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 Pilgrim Hotel Reviews

Find out more about Pilgrim

Everything you need to know about Pilgrim 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 Pilgrim 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 Pilgrim holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pilgrim holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pilgrim. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pilgrim 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 Pilgrim holiday rentals we have selected for you start as low as AU$191 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pilgrim rentals

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

Frequently asked questions

Can I find a holiday rental in Pilgrim?

Yes, there are holiday rentals close to the most popular sights in Pilgrim, or you can select a more secluded option if you're looking for a relaxing stay.

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

Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace: This holiday home rental outside of Pilgrim is located in the mountains, and has an indoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Pilgrim?

While you're exploring the area, Hatfield McCoy Trail - Buffalo Mountain Trail System and Jenny Wiley State Resort Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Williamson Memorial Fieldhouse and The Coal House.

What are holiday rentals like in Pilgrim?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pilgrim. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip.