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Pilgrim Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Pilgrim vacation rentals

Terrace/patio

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.
$295 nightly
The price is $297
Jul 28 - Jul 29
Total with taxes and fees
The Mountain Magnolia *Hot tub on private deck*
Smart TV, fireplace

Appalachian Hideaways Cabin #2

Appalachian Hideaways Cabin #2
Williamson
9.4 out of 10, Exceptional, (16 reviews)
"Nice little spot to stay after a day riding the trails."
United States
Curtis J.
$181 nightly
The price is $201
Jul 28 - Jul 29
Total with taxes and fees
Appalachian Hideaways Cabin #2
Exterior

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, (8 reviews)
"Perfect little cottage "
Canada
Alisha G.
$128 nightly
The price is $142
Aug 3 - Aug 4
Total with taxes and fees
Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery
Outdoor dining

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.
$134 nightly
The price is $144
Jul 28 - Jul 29
Total with taxes and fees
Modern Escape
Coffee/tea maker, fridge, microwave, oven

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
9.6 out of 10, Exceptional, (14 reviews)
"House was very clean and well kept close to gas station restaurant and trail systems"
United States
Eric M.
$169 nightly
The price is $188
Aug 2 - Aug 3
Total with taxes and fees
Walking distance to gas station, riding passes, and the famous Sherry Bo’s diner
Property grounds

The Boons Camp Cabin

The Boons Camp Cabin
Boons Camp
$345 nightly
The price is $348
Aug 2 - Aug 3
Total with taxes and fees
The Boons Camp Cabin
Interior

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
$280 nightly
The price is $297
Jul 28 - Jul 29
Total with taxes and fees
Sheppard's Holler: Your WV Adventure Home
Smart TV

Inspiration Station

Inspiration Station
Pikeville
9.2 out of 10, Wonderful, (9 reviews)
"My husband and I came down to Pikeville for the Hillbilly Days Festival. This cabin was spotless, very nicely decorated, SUPER easy to check in. It was very quiet and peaceful. Exactly what we wanted and needed. Super close to restaurants and stores, and tourist attractions. We LOVED it here and will for sure be back."
United States
Lisa S.
$160 nightly
The price is $172
Aug 2 - Aug 3
Total with taxes and fees
Inspiration Station
Coffee/tea maker, fridge, microwave, oven

Cozy Home in Heart of Prestonsburg

Cozy Home in Heart of Prestonsburg
Prestonsburg
10.0 out of 10, Exceptional, (13 reviews)
"The house was very convenient to downtown area. Everything was clean and we really enjoyed our stay. We will definitely book again on our next trip!"
United States
Ashleigh g.
$157 nightly
The price is $178
Jul 28 - Jul 29
Total with taxes and fees
Cozy Home in Heart of Prestonsburg
Property grounds

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, (45 reviews)
"Very easy access to trail system"
United States
stehen
$235 nightly
The price is $262
Jul 28 - Jul 29
Total with taxes and fees
Creekside Retreat, 3 bedroom, Large parking, Picnic area. Across from Trail 14
Exterior detail

The Nook in Downtown Pikeville

The Nook in Downtown Pikeville
Pikeville
9.6 out of 10, Exceptional, (7 reviews)
"Apartment was as described. "
United States
Chris R.
$159 nightly
The price is $182
Jul 28 - Jul 29
Total with taxes and fees
The Nook in Downtown Pikeville
Dining

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, (12 reviews)
"Very nice places. Clean and cute. Love the surrounding Mountain View’s. Definitely on my list to stay again."
United States
Kevin S.
$138 nightly
The price is $152
Aug 2 - Aug 3
Total with taxes and fees
Cozy Tiny Home Quiet 1/1 Close to Riding Trails
Coffee/tea maker, fridge, microwave, oven

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

Papa Bear's Den!! “The perfect location to visit the trails”
Sarah Ann
10.0 out of 10, Exceptional, (18 reviews)
"What a wonderful stay we had. The house was fabulous and had everything you could think of. We would definitely stay here again "
United States
Lesa R.
$208 nightly
The price is $231
Aug 7 - Aug 8
Total with taxes and fees
Papa Bear's Den!! “The perfect location to visit the trails”
Smart TV

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)
"very clean, plenty of room, the garage was very helpful to put the machines in for the evenings, great host, and the nice grounds keeper living across the road was great, "
United States
Anonymous traveler
$307 nightly
The price is $342
Jul 28 - Jul 29
Total with taxes and fees
2 miles from Buffalo Mountain Trail 8 Devil Anse
Outdoor dining

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.
$393 nightly
The price is $437
Jul 28 - Jul 29
Total with taxes and fees
Ryder's Retreat overlooking the city of Williamson!
Dining

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, (12 reviews)
"Check in was easy. Great communication and pictures fairly represented the actual stay "
United States
Jordan B.
$249 nightly
The price is $277
Aug 2 - Aug 3
Total with taxes and fees
Mama Bears den “The perfect location to visit the Hatfield and McCoy trails”
Outdoor dining

*The Decked out Den*

*The Decked out Den*
Delbarton
10.0 out of 10, Exceptional, (19 reviews)
"Great place to stay, conveniently located to ATV trailheads."
United States
Jeff B.
$372 nightly
The price is $404
Jul 28 - Jul 29
Total with taxes and fees
*The Decked out Den*
Property grounds

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
9.2 out of 10, Wonderful, (14 reviews)
"Great place right in the center of the trail system and nice, quiet, private. Easy access to town also trails Buffalo, Devil Anse, Rock House, Braveheart. If you want your own private setting without the resort or cabins with bunch of neighbors than this is the place. Enjoyed ever second of our stay. Thanks "
United States
Adam S.
$413 nightly
The price is $459
Jul 28 - Jul 29
Total with taxes and fees
Nice private home in Matewan, close to trails! Hottub, Pool, fire pits & games!
Exterior

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)
"House was perfect for a group of guys hitting the trails. Will definitely book again. Thanks Joanna!"
United States
Anonymous traveler
$720 nightly
The price is $801
Aug 17 - Aug 18
Total with taxes and fees
Large spacious house with ample parking for large groups.
Smart TV, books

Cozy Apartment with onsite restaurant in Logan WV Close to Hatfield McCoy Trail

Cozy Apartment with onsite restaurant in Logan WV Close to Hatfield McCoy Trail
Logan
9.6 out of 10, Exceptional, (10 reviews)
"Great place to stay. Restaurant right down stairs is amazing. Owners are very helpful and nice "
United States
Matthew S.
$395 nightly
The price is $440
Jul 28 - Jul 29
Total with taxes and fees
Cozy Apartment with onsite restaurant in Logan WV Close to Hatfield McCoy Trail
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

Brookshire Inn

Brookshire Inn

10/10 Excellent
"Very nice. Older establishment, a few very tiny repairs could be made. Very clean. No funny or unpleasant smells(smoke, animals musky..old). Would stay there again."
Linda 1-night trip
Posted 5 hours ago
Brookshire Inn

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 $142 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.

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.