Pilgrim Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Pilgrim vacation rentals

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
9.4 out of 10, Exceptional, (10 reviews)
"Everything was wonderful, made traveling to a family reunion easy."
United States
Melissa
The price is CA $142
CA $257 total
includes taxes & fees
Jun 1 - Jun 2
Walking distance to gas station, riding passes, and the famous Sherry Bo’s diner

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, (43 reviews)
"Amazing place to stay, it is directly across from a trail head,parking lot is full of space for multiple truck and trailers, the inside is very clean, the owners are excellent at replying, i will highly recommend for a great weekend stay, i will be back in the future!"
United States
Doug H.
The price is CA $235
CA $359 total
includes taxes & fees
Jun 1 - Jun 2
Creekside Retreat, 3 bedroom, Large parking, Picnic area. Across from Trail 14

Appalachian Hideaways Cabin #2

Appalachian Hideaways Cabin #2
Williamson
9.6 out of 10, Exceptional, (14 reviews)
"Nice little spot to stay after a day riding the trails."
United States
Curtis J.
The price is CA $149
CA $275 total
includes taxes & fees
Jun 7 - Jun 8
Appalachian Hideaways Cabin #2

Cozy Tiny Home Quiet 1/1 Close to Riding Trails

Cozy Tiny Home Quiet 1/1 Close to Riding Trails
Martin
9.4 out of 10, Exceptional, (9 reviews)
"We had the most wonderful stay! We actually got a little lost on the way in, and the host went above and beyond to help guide us and even helped us get settled into the house. That meant so much after a long week.The tiny home was absolutely beautiful — spotless, cozy, and thoughtfully put together. It may be small in size, but it’s truly full of love. There was even extra Valentine’s gifts - such a sweet and unexpected touch that made our stay even more special.The peaceful rain in the...
United States
Bri E.
The price is CA $93
CA $209 total
includes taxes & fees
Jun 4 - Jun 5
Cozy Tiny Home Quiet 1/1 Close to Riding Trails

Backwoods Bungalow

Backwoods Bungalow
Pikeville
10.0 out of 10, Exceptional, (13 reviews)
"I was one of the best places I have ever stayed at. I loved it. The Josh is a great host and was there anytime to help when I needed him. "
United States
Maqbool
The price is CA $116
CA $213 total
includes taxes & fees
Jun 3 - Jun 4
Backwoods Bungalow

The Mountain Magnolia *Hot tub on private deck*

The Mountain Magnolia *Hot tub on private deck*
Inez
10.0 out of 10, Exceptional, (4 reviews)
"Room was clean hot tub was nice and spacious its more secluded then most places 10/10 would book again! Also very well stocked!"
United States
Paige S.
The price is CA $246
CA $398 total
includes taxes & fees
Jun 8 - Jun 9
The Mountain Magnolia *Hot tub on private deck*

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.
The price is CA $345
CA $608 total
includes taxes & fees
Jun 1 - Jun 2
Cozy Apartment with onsite restaurant in Logan WV Close to Hatfield McCoy Trail

The Palace on Charles is the perfect vacation getaway.

The Palace on Charles is the perfect vacation getaway.
Logan
The price is CA $991
CA $1,251 total
includes taxes & fees
Jun 1 - Jun 2
The Palace on Charles is the perfect vacation getaway.

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, (17 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.
The price is CA $166
CA $339 total
includes taxes & fees
Jun 20 - Jun 21
Papa Bear's Den!! “The perfect location to visit the trails”

Inspiration Station

Inspiration Station
Pikeville
9.0 out of 10, Wonderful, (8 reviews)
"It was an absolute beautiful little place, decorated great. Everything was so planned out down to shampoo and conditner in the bathroom. Thank you for the opportunity to enjoy your place!"
United States
Dee C.
The price is CA $138
CA $237 total
includes taxes & fees
Jun 4 - Jun 5
Inspiration Station

Modern Escape

Modern Escape
Pikeville
9.8 out of 10, Exceptional, (8 reviews)
"Super nice place will stay again for sure. "
United States
Rosa M.
The price is CA $102
CA $198 total
includes taxes & fees
Jun 3 - Jun 4
Modern Escape

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, (11 reviews)
"Very clean, no issues. Great location! One of the nicer houses we’ve stayed in WV trails, very well stocked in great condition. Highly recommend."
United States
Paul H.
The price is CA $276
CA $566 total
includes taxes & fees
Jun 29 - Jun 30
Nice private home in Matewan, close to trails! Hottub, Pool, fire pits & games!

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, (6 reviews)
"We absolutely loved this home. Plenty of rooms and parking for our rides and a nice garage to empty in so we didn’t drag mud and dirt everywhere. Love the decorating fall touches made you feel welcomed. Definitely will be back. "
United States
Martha
The price is CA $639
CA $1,163 total
includes taxes & fees
Jun 23 - Jun 24
Large spacious house with ample parking for large groups.

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, (5 reviews)
"Perfect little cottage "
Canada
Alisha G.
The price is CA $127
CA $210 total
includes taxes & fees
Jun 15 - Jun 16
Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery

Ryder's Retreat overlooking the city of Williamson!

Ryder's Retreat overlooking the city of Williamson!
Williamson
9.0 out of 10, Wonderful, (6 reviews)
"One end of the neighborhood is sketch, other end is nice. People were nice to us in both ends."
United States
Michael K.
The price is CA $371
CA $602 total
includes taxes & fees
Jun 2 - Jun 3
Ryder's Retreat overlooking the city of Williamson!

Cozy Home in Heart of Prestonsburg

Cozy Home in Heart of Prestonsburg
Prestonsburg
10.0 out of 10, Exceptional, (13 reviews)
"Clean but noisy location late into night"
United States
Juanita S.
The price is CA $134
CA $246 total
includes taxes & fees
Jun 1 - Jun 2
Cozy Home in Heart of Prestonsburg

The Boons Camp Cabin

The Boons Camp Cabin
Boons Camp
The price is CA $116
CA $481 total
includes taxes & fees
Jun 1 - Jun 2
The Boons Camp Cabin

Sheppard's Holler: Your WV Adventure Home

Sheppard's Holler: Your WV Adventure Home
lenore
10.0 out of 10, Exceptional, (5 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 $200
CA $408 total
includes taxes & fees
Jun 3 - Jun 4
Sheppard's Holler: Your WV Adventure Home

6-Bedroom Master Deluxe, 5.5-Bath Log Cabin with Theater Room

6-Bedroom Master Deluxe, 5.5-Bath Log Cabin with Theater Room
chapmanville
The price is CA $1,360
CA $2,091 total
includes taxes & fees
Jun 12 - Jun 13
6-Bedroom Master Deluxe, 5.5-Bath Log Cabin with Theater Room

*The Decked out Den*

*The Decked out Den*
Delbarton
10.0 out of 10, Exceptional, (18 reviews)
"Great place to stay, conveniently located to ATV trailheads."
United States
Jeff B.
The price is CA $310
CA $557 total
includes taxes & fees
Jun 10 - Jun 11
*The Decked out Den*
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

The Mountain Magnolia *Hot tub on private deck*: This vacation home rental near Pilgrim is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

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 Roy Collier Community Center and Loretta Lynn's Birthplace - Butcher Hollow.

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.