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Pilgrim Vacation Rentals

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Our top choices for Pilgrim vacation rentals

1. Appalachian Hideaways Cabin #2

Appalachian Hideaways Cabin #2
Williamson
9.4 out of 10, Exceptional, (16 reviews)
The price is CA $150
CA $276 total
includes taxes & fees
Aug 31 - Sep 1
Appalachian Hideaways Cabin #2

2. Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery

Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery
Forest Hills
10.0 out of 10, Exceptional, (9 reviews)
"Could not have asked for a smoother check-in and out! The property is perfect for what I needed and the attention to the little details that made my stay easier (coffee pods, etc) was so appreciated!! Will stay here again when I come back to Pike Co for sure!!"
United States
Deborah C.
The price is CA $115
CA $198 total
includes taxes & fees
Sep 8 - Sep 9
Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery

3. The Mountain Magnolia *Hot tub on private deck*

The Mountain Magnolia *Hot tub on private deck*
Inez
10.0 out of 10, Exceptional, (5 reviews)
"Tina and Jake were excellent hosts! Loved their cozy cabin and will be back!"
United States
Gavin L.
The price is CA $255
CA $413 total
includes taxes & fees
Aug 31 - Sep 1
The Mountain Magnolia *Hot tub on private deck*

4. Modern Escape

Modern Escape
Pikeville
9.8 out of 10, Exceptional, (9 reviews)
"Super nice place will stay again for sure. "
United States
Rosa M.
The price is CA $103
CA $200 total
includes taxes & fees
Sep 3 - Sep 4
Modern Escape

5. Walking distance to gas station, riding passes, and the famous Sherry Bo’s diner

Walking distance to gas station, riding passes, and the famous Sherry Bo’s diner
Delbarton
9.8 out of 10, Exceptional, (16 reviews)
"Everything about the place was excellent! I have not one negative thing to say."
United States
Michael
The price is CA $143
CA $259 total
includes taxes & fees
Aug 31 - Sep 1
Walking distance to gas station, riding passes, and the famous Sherry Bo’s diner

6. Cozy Home in Heart of Prestonsburg

Cozy Home in Heart of Prestonsburg
Prestonsburg
10.0 out of 10, Exceptional, (13 reviews)
The price is CA $135
CA $248 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Home in Heart of Prestonsburg

7. Ryder's Retreat overlooking the city of Williamson!

Ryder's Retreat overlooking the city of Williamson!
Williamson
9.2 out of 10, Wonderful, (7 reviews)
"The house was very nice. We didn’t care for the neighborhood. The people that owned the house was nice and very helpful!!! "
United States
Linda P.
The price is CA $250
CA $444 total
includes taxes & fees
Sep 7 - Sep 8
Ryder's Retreat overlooking the city of Williamson!

8. Inspiration Station

Inspiration Station
Pikeville
9.2 out of 10, Wonderful, (9 reviews)
"Great place to stay for a solo outing or couples getaway. The road leading up to the property is pretty dicey, but the place itself was great and the host was fantastic!"
United States
John H.
The price is CA $139
CA $239 total
includes taxes & fees
Aug 31 - Sep 1
Inspiration Station

9. The Boons Camp Cabin

The Boons Camp Cabin
Boons Camp
The price is CA $120
CA $489 total
includes taxes & fees
Aug 31 - Sep 1
The Boons Camp Cabin

10. Sheppard's Holler: Your WV Adventure Home

Sheppard's Holler: Your WV Adventure Home
lenore
10.0 out of 10, Exceptional, (6 reviews)
"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 CA $229
CA $439 total
includes taxes & fees
Sep 7 - Sep 8
Sheppard's Holler: Your WV Adventure Home

11. RV Site 8 Camper - Hatfield McCoy Trails

RV Site 8 Camper - Hatfield McCoy Trails
Wilkinson
The price is CA $70
CA $110 total
includes taxes & fees
Aug 31 - Sep 1
RV Site 8 Camper - Hatfield McCoy Trails

12. Creekside Retreat, 3 bedroom, Large parking, Picnic area. Across from Trail 14

Creekside Retreat, 3 bedroom, Large parking, Picnic area. Across from Trail 14
Delbarton
9.8 out of 10, Exceptional, (47 reviews)
"Very easy access to trail system"
United States
stehen
The price is CA $237
CA $359 total
includes taxes & fees
Aug 31 - Sep 1
Creekside Retreat, 3 bedroom, Large parking, Picnic area. Across from Trail 14

13. Cozy Tiny Home Quiet 1/1 Close to Riding Trails

Cozy Tiny Home Quiet 1/1 Close to Riding Trails
Martin
9.6 out of 10, Exceptional, (13 reviews)
"Everything was perfect until bed time. I the place but the mattress killed my back. "
United States
Danail H.
The price is CA $94
CA $211 total
includes taxes & fees
Sep 6 - Sep 7
Cozy Tiny Home Quiet 1/1 Close to Riding Trails

14. Suite 1 Trail 10 HMT

Suite 1 Trail 10 HMT
South Williamson
The price is CA $174
CA $333 total
includes taxes & fees
Sep 13 - Sep 14
Suite 1 Trail 10 HMT

15. Mama Bears den “The perfect location to visit the Hatfield and McCoy trails”

Mama Bears den “The perfect location to visit the Hatfield and McCoy trails”
Sarah Ann
10.0 out of 10, Exceptional, (13 reviews)
"Check in was easy. Great communication and pictures fairly represented the actual stay "
United States
Jordan B.
The price is CA $200
CA $384 total
includes taxes & fees
Sep 7 - Sep 8
Mama Bears den “The perfect location to visit the Hatfield and McCoy trails”

16. 2 miles from Buffalo Mountain Trail 8 Devil Anse

2 miles from Buffalo Mountain Trail 8 Devil Anse
Delbarton
9.6 out of 10, Exceptional, (12 reviews)
"Beautifully decorated. Very clean. Great location. Plenty of room for our 5 guests. Loved the back porch. The garage is a huge bonus. Would definitely stay here again!"
United States
Debbie K.
The price is CA $278
CA $474 total
includes taxes & fees
Aug 31 - Sep 1
2 miles from Buffalo Mountain Trail 8 Devil Anse

17. Papa Bear's Den!! “The perfect location to visit the trails”

Papa Bear's Den!! “The perfect location to visit the trails”
Sarah Ann
9.8 out of 10, Exceptional, (20 reviews)
"Excellent place to stay"
United States
Austin H.
The price is CA $244
CA $442 total
includes taxes & fees
Sep 3 - Sep 4
Papa Bear's Den!! “The perfect location to visit the trails”

18. *The Decked out Den*

*The Decked out Den*
Delbarton
10.0 out of 10, Exceptional, (19 reviews)
"Excellent place to stay! Clean Cool,"
United States
Ryan Z.
The price is CA $313
CA $559 total
includes taxes & fees
Sep 18 - Sep 19
*The Decked out Den*

19. Nice private home in Matewan, close to trails! Hottub, Pool, fire pits & games!

Nice private home in Matewan, close to trails! Hottub, Pool, fire pits & games!
Matewan
9.4 out of 10, Exceptional, (17 reviews)
"Great location and very nice host. Check in and out was a breeze. Very positive experience all around."
United States
Blake O.
The price is CA $313
CA $616 total
includes taxes & fees
Aug 31 - Sep 1
Nice private home in Matewan, close to trails! Hottub, Pool, fire pits & games!

20. Large spacious house with ample parking for large groups.

Large spacious house with ample parking for large groups.
Delbarton
10.0 out of 10, Exceptional, (7 reviews)
The price is CA $648
CA $1,177 total
includes taxes & fees
Sep 8 - Sep 9
Large spacious house with ample parking for large groups.
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pilgrim. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Pilgrim?

Yes, we offer vacation rentals close to well known sights in Pilgrim, or you can choose a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Pilgrim?

Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace: This vacation home rental near Pilgrim is located in the mountains and has an indoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 12 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, an arcade game room, and a hot tub so you can immerse yourself in your vacation.

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 larger area, you’ll find Loretta Lynn's Birthplace - Butcher Hollow and Loretta Lynn's Home.

What are vacation rentals like in Pilgrim?

Vacation rentals are privately owned properties you can reserve for several days or longer in Pilgrim. Vacation rentals feature extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.