Pilgrim Vacation Rentals

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Oct 24 - Oct 26
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Nov 7 - Nov 9
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Jan 2 - Jan 4

Vacation Rentals in Pilgrim

Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
Interior

Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace

9.8 out of 10, Exceptional, (11)
"Great place to stay for our family. Loved everything about the location, house, pool, and overall value."
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails
Outdoor pool

Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails

9.6 out of 10, Exceptional, (21)
"We really enjoyed our stay. The home was extremely spacious for all of us. The home was extremely clean And Welcoming when you enter. We will Definitely lease this property again on our next trip. "
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails
Trailside Lodge | 10 Sec to Trail, Hot Tub + Fire Pit
Interior

Trailside Lodge | 10 Sec to Trail, Hot Tub + Fire Pit

10.0 out of 10, Exceptional, (5)
"Clean place one of the best cabins we have ever stayed in. Highly recommended to anyone great location as well "
Trailside Lodge | 10 Sec to Trail, Hot Tub + Fire Pit
NEW PARADISE RETREAT - Hatfield Mccoy Trails - Rent 1-3 Cabins, Sleep up to 18
Terrace/patio

NEW PARADISE RETREAT - Hatfield Mccoy Trails - Rent 1-3 Cabins, Sleep up to 18

10.0 out of 10, Exceptional, (13)
"Best place out of the 3 times that we have ever had when visiting the HMT trails, location and the accuracy of being told that you can fit a 28’ trailer and truck into the driveway to get to the cabin with plenty of space to park"
NEW PARADISE RETREAT - Hatfield Mccoy Trails - Rent 1-3 Cabins, Sleep up to 18
Mountain Laurel House
Exterior

Mountain Laurel House

10.0 out of 10, Exceptional, (50)
"Great place to stay. Very clean, they made us feel like it was our own home."
Mountain Laurel House
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
Property grounds

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"
$284 nightly
The price is $309
Nov 3 - Nov 4
Total with taxes and fees
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
Private house sleeps 8 in Logan. Located near HMTS access points, dining, shops
Outdoor dining

Private house sleeps 8 in Logan. Located near HMTS access points, dining, shops

10.0 out of 10, Exceptional, (2)
"Great stay, beautiful new spot that we will be back to. Great communication. Highly recommend "
Private house sleeps 8 in Logan. Located near HMTS access points, dining, shops
Unit B: 20 Sec Ride to Trails, Sleeps 10. King
Property grounds

Unit B: 20 Sec Ride to Trails, Sleeps 10. King

9.0 out of 10, Wonderful, (14)
"would stay here again "
Unit B: 20 Sec Ride to Trails, Sleeps 10. King
Devil Anse Off Road Lodging Hatfield & McCoy Trail House
Fridge, microwave, oven, stovetop

Devil Anse Off Road Lodging Hatfield & McCoy Trail House

10.0 out of 10, Exceptional, (46)
"Great place to stay!"
Devil Anse Off Road Lodging Hatfield & McCoy Trail House
Papa Bear's Den!! “The perfect location to visit the trails”
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (11)
"Clean and comfortable. "
$198 nightly
The price is $220
Nov 3 - Nov 4
Total with taxes and fees
Papa Bear's Den!! “The perfect location to visit the trails”
2 miles from Buffalo Mountain Trail 8 Devil Anse
Fridge, microwave, oven, stovetop

2 miles from Buffalo Mountain Trail 8 Devil Anse

9.6 out of 10, Exceptional, (7)
"The house was very clean and comfy! We'll definitely be back!"
2 miles from Buffalo Mountain Trail 8 Devil Anse
Appalachian Hideaways
Living area

Appalachian Hideaways

9.2 out of 10, Wonderful, (7)
"Great place "
Appalachian Hideaways
Hatfield McCoy Trails! Newly renovated 3 bedroom house with ATV trail access.
Fridge, microwave, oven, stovetop

Hatfield McCoy Trails! Newly renovated 3 bedroom house with ATV trail access.

9.8 out of 10, Exceptional, (32)
"We had a good time staying here."
Hatfield McCoy Trails! Newly renovated 3 bedroom house with ATV trail access.
Mama Bears den “The perfect location to visit the Hatfield and McCoy trails”
4 bedrooms, iron/ironing board, WiFi, bed sheets

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

10.0 out of 10, Exceptional, (7)
"Highly recommend staying at the mama bear den. Beautiful house and perfect for a group. We drove from south dakota and felt right at home. Gary is an outstanding host and we will definitely be back to stay again."
$198 nightly
The price is $220
Nov 2 - Nov 3
Total with taxes and fees
Mama Bears den “The perfect location to visit the Hatfield and McCoy trails”
Luxury Estate nestled atop stunning mountaintop golf course!
Interior

Luxury Estate nestled atop stunning mountaintop golf course!

2.0 star property
10.0 out of 10, Exceptional, (6)
"The house is beautiful, and located in the mountains overlooking breathtaking scenery. It is surrounded by a golf course. It is an easy drive to Prestonsburg. Our host was lovely, and checked on us regularly. We really could not have been more pleased. Thank you!"
Luxury Estate nestled atop stunning mountaintop golf course!
Creekside Retreat, 3 bedroom, Large parking, Picnic area. Across from Trail 14
Smart TV

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"
$233 nightly
The price is $259
Oct 12 - Oct 13
Total with taxes and fees
Creekside Retreat, 3 bedroom, Large parking, Picnic area. Across from Trail 14
Walking distance to gas station/riding passes, and the famous Sherry Bo’s diner
Fridge, microwave, oven, stovetop

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."
$169 nightly
The price is $188
Oct 13 - Oct 14
Total with taxes and fees
Walking distance to gas station/riding passes, and the famous Sherry Bo’s diner
A & B TRAIL HOUSE @ Hatfield-McCoy Trails, 5 Beds Plus Futon 2 Couches & 2 Baths
Dining

A & B TRAIL HOUSE @ Hatfield-McCoy Trails, 5 Beds Plus Futon 2 Couches & 2 Baths

9.8 out of 10, Exceptional, (16)
"Very clean little property with room for everyone"
A & B TRAIL HOUSE @ Hatfield-McCoy Trails, 5 Beds Plus Futon 2 Couches & 2 Baths
5th Wheel RV On Permanent Site ,Near Hatfield McCoy Sites
Microwave, oven, stovetop, paper towels

5th Wheel RV On Permanent Site ,Near Hatfield McCoy Sites

9.0 out of 10, Wonderful, (2)
"Very pet friendly. Excellent hosts. "
$133 nightly
The price is $148
Oct 15 - Oct 16
Total with taxes and fees
5th Wheel RV On Permanent Site ,Near Hatfield McCoy Sites
Turkey Creek Retreats
Exterior

Turkey Creek Retreats

10.0 out of 10, Exceptional, (27)
"Would definitely recommend for everyone"
Turkey Creek Retreats
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

Hampton Inn Pikeville

Hampton Inn Pikeville

10/10 Excellent
"One of the cleanest hotels we have stayed in. Great breakfast with lots of options. Customer service was great. "
Kenneth 2-night trip
Posted 2 days ago
Hampton Inn Pikeville

Find out more about Pilgrim

Find out more about Pilgrim

Everything you need to know about Pilgrim vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pilgrim vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pilgrim vacation 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 low season months. For more hustle and bustle, you may prefer to visit Pilgrim in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $148 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pilgrim rentals

At Expedia, we put the best Pilgrim vacation 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 vacation.

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 11 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 Williamson Memorial Fieldhouse and The Coal House.

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.