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Pilgrim Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Pilgrim holiday rentals

A wooden interior with a sofa, a blue armchair, and a potted plant.

1. Inspiration Station

Inspiration Station
Pikeville
9.2 out of 10, Wonderful, (10 reviews)
"Everything was wonderful. It was peaceful and quiet. We loved the resident cat. Just a beautiful cabin and beautiful place! We will stay down here anytime we come to visit in the area."
United States
Susan
The price is NZ$306
includes taxes & fees
14 Oct - 15 Oct
Inspiration Station
A dining area with a marble table, black chairs, a potted plant, a window with a view of greenery, and a mounted TV.

2. Cozy studio on US 23 between Pikeville and Prestonsburg

Cozy studio on US 23 between Pikeville and Prestonsburg
Harold
9.6 out of 10, Exceptional, (5 reviews)
"I stayed at this place for a 2nd time on a hunting trip. Nice little place to lay your head."
United States
Jeremy
The price is NZ$280
includes taxes & fees
14 Oct - 15 Oct
Cozy studio on US 23 between Pikeville and Prestonsburg
A two-story house with a porch and a staircase.

3. 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
9.8 out of 10, Exceptional, (10 reviews)
"It was a peaceful and quiet place. Very clean and tidy. Has it's own driveway to park. The host was amazing, nice and very responsive."
United States
deborah j.
The price is NZ$262
includes taxes & fees
26 Oct - 27 Oct
Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery
A hot tub with seating and a table, surrounded by a wooden deck and trees.

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

The Mountain Magnolia *Hot tub on private deck*
Inez
10.0 out of 10, Exceptional, (6 reviews)
"Tina and Jake were excellent hosts! Loved their cozy cabin and will be back!"
United States
Gavin L.
The price is NZ$508
includes taxes & fees
25 Oct - 26 Oct
The Mountain Magnolia *Hot tub on private deck*
A cozy living room with a sofa, a chair, a TV, and a fireplace.

5. 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.
The price is NZ$353
includes taxes & fees
20 Oct - 21 Oct
Appalachian Hideaways Cabin #2
A rustic cabin surrounded by lush greenery and a fenced area.

6. The Boons Camp Cabin

The Boons Camp Cabin
Boons Camp
The price is NZ$606
includes taxes & fees
14 Oct - 15 Oct
The Boons Camp Cabin
A covered deck with a grill, two chairs, and a table.

7. 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 NZ$256
includes taxes & fees
14 Oct - 15 Oct
Modern Escape
A wooden interior with a kitchen, a sofa, a ceiling fan, and a sign reading 'Backwoods Bungalow'.

8. Backwoods Bungalow

Backwoods Bungalow
Pikeville
10.0 out of 10, Exceptional, (13 reviews)
"Worked out very nice for our stay. "
United States
Cole A.
The price is NZ$287
includes taxes & fees
20 Oct - 21 Oct
Backwoods Bungalow
A compact kitchen with a refrigerator, microwave, stove, and cabinets.

9. 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, (17 reviews)
"Everything about the place was excellent! I have not one negative thing to say."
United States
Michael
The price is NZ$332
includes taxes & fees
21 Oct - 22 Oct
Walking distance to gas station, riding passes, and the famous Sherry Bo’s diner
A kitchen with a built-in oven, microwave, and stainless steel range.

10. 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.
The price is NZ$318
includes taxes & fees
20 Oct - 21 Oct
Cozy Home in Heart of Prestonsburg
A spacious dining area with a wooden table and chairs, a kitchen in the background, and a ceiling with a grid pattern.

11. Suite 1 Trail 10 HMT

Suite 1 Trail 10 HMT
South Williamson
10.0 out of 10, Exceptional, (1 review)
"Great value for the accommodations. Great location. Some difficulty in getting checking information from host. Otherwise a good experience overall and would stay there again."
United States
Cammy R.
The price is NZ$426
includes taxes & fees
14 Oct - 15 Oct
Suite 1 Trail 10 HMT
A wooden deck with two chairs and a red door leading to a covered area.

12. NO RV? NO PROBLEM! STAY IN OUR FAMILY-FRIENDLY, COZY COTTAGES.

NO RV? NO PROBLEM! STAY IN OUR FAMILY-FRIENDLY, COZY COTTAGES.
Staffordsville
10.0 out of 10, Exceptional, (1 review)
"Very clean. Within just a few miles of attractions. Hosts were the best at communicating, and attentive to all our needs.I will recommend this to friends!"
United States
Becky M.
The price is NZ$200
includes taxes & fees
14 Oct - 15 Oct
NO RV? NO PROBLEM! STAY IN OUR FAMILY-FRIENDLY, COZY COTTAGES.
A bathroom with a shower curtain depicting a forest scene with a cabin, bear, and birds.

13. 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 NZ$478
includes taxes & fees
2 Nov - 3 Nov
Sheppard's Holler: Your WV Adventure Home
A wooden interior with two doors, a sign reading 'Wanda's Cafe,' and two woven plates on the wall.

14. Wanderers Oasis

Wanderers Oasis
Pikeville
10.0 out of 10, Exceptional, (1 review)
"Very quaint and quiet. Nice relaxing evening in the woods and mountains."
United States
Paul F.
The price is NZ$288
includes taxes & fees
8 Nov - 9 Nov
Wanderers Oasis
A wooden deck with red Adirondack chairs and a table, overlooking a town and mountains.

15. 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 NZ$560
includes taxes & fees
25 Oct - 26 Oct
Ryder's Retreat overlooking the city of Williamson!
A wooden bench overlooking a river, surrounded by lush greenery and a stone wall.

16. 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, (48 reviews)
"Very easy access to trail system"
United States
stehen
The price is NZ$459
includes taxes & fees
19 Oct - 20 Oct
Creekside Retreat, 3 bedroom, Large parking, Picnic area. Across from Trail 14
A wooden dining table with a woven placemat, a tray with a mug and a sign saying "STAY COZY," and a small sign that reads "let it."

17. 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, (14 reviews)
"We found it to be a very clean, cozy, and quiet get-away!"
United States
Kimberly H.
The price is NZ$271
includes taxes & fees
14 Oct - 15 Oct
Cozy Tiny Home Quiet 1/1 Close to Riding Trails
A cozy living room with a sofa, a ceiling fan, and a patterned rug.

18. 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, (13 reviews)
"Great place to stay really close to buffalo mountain trails along with outlaw trails. Plenty of places to eat near by will definitely stay here again"
United States
Brian D.
The price is NZ$603
includes taxes & fees
14 Oct - 15 Oct
2 miles from Buffalo Mountain Trail 8 Devil Anse
A wooden deck with a red umbrella, a black chair, and a table.

19. *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 NZ$718
includes taxes & fees
24 Oct - 25 Oct
*The Decked out Den*
A bedroom with a wooden bed, a dresser, a mirror, and a painting on the wall.

20. Historic Cottage Near PMC, UPIKE and Arena

Historic Cottage Near PMC, UPIKE and Arena
Pikeville
The price is NZ$441
includes taxes & fees
20 Oct - 21 Oct
Historic Cottage Near PMC, UPIKE and Arena
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

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!

10/10 Excellent
"Tons of room and very close to multiple trailheads. Plenty of beds if you have a large group. Hot tub was nice after a long day out on the trails. Very private setting with plenty of room to park trucks and trailers. Can't wait to come back and ride the hatfields again!"
Jon K. 5-night trip
Posted 1 hour ago
Nice private home in Matewan, close to trails! Hottub, Pool, fire pits & games!

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 favorite 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 depends 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 NZ$200 per night. Entering your travel dates in the search wizard you might find 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?

A & B TRAIL HOUSE @ Hatfield-McCoy Trails, 5 Beds Plus Futon 2 Couches & 2 Baths: This holiday home rental outside of Pilgrim is located in the mountains, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 Southern West Virginia Community Technical College - Williamson Campus and Loretta Lynn's Birthplace - Butcher Hollow.

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.