Pilgrim Holiday Rentals

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Holiday Rentals in Pilgrim

Newly est. cabin close to trails, gas and great food!

10.0 out of 10, Exceptional, (31)
"The place was great and the location was perfect for us."
Newly est. cabin close to trails, gas and great food!

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

9.6 out of 10, Exceptional, (19)
"We had a great time. The house is beautiful and very spacious. Location is perfect because it’s close to everything. Neighbors were very nice! Host was super nice and very accommodating. We will definitely come back and stay again! Dirt Days was a lot of fun for us and my nephews. The vendors were very friendly. The town has a lot of cool history."
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails

Creekside ATV Lodge. Newly Renovated, sleeps 10. Direct Access to trail 31 & 32

9.0 out of 10, Wonderful, (20)
"Place was very clean and had alot of parking for trailers. Close to trails and town, would definitely come back "
Creekside ATV Lodge. Newly Renovated, sleeps 10. Direct Access to trail 31 & 32

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

9.8 out of 10, Exceptional, (34)
"We had a great weekend here, plenty of parking space, house was neat and clean with everything we could have needed. Plenty of outdoor gathering space and communication with host were A . Will be back again."
The price is AU$441
includes taxes & fees
27 Nov - 28 Nov
Creekside Retreat, 3 bedroom, Large parking, Picnic area. Across from Trail 14

Cozy Home in Heart of Prestonsburg

10.0 out of 10, Exceptional, (6)
"Stopped in the area to visit family that has passed on and to find our family cemetery. Was unable to find the cemetery but still enjoyed my trip. We also visted Loretta Lynns place."
The price is AU$369
includes taxes & fees
26 Nov - 27 Nov
Cozy Home in Heart of Prestonsburg

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

9.8 out of 10, Exceptional, (30)
"Well maintained And verry clean Thank you, Steph &Jay,"
Hatfield McCoy Trails! Newly renovated 3 bedroom house with ATV trail access.

💙The Mountain Mama💛 Trail Riders “Home Away From Home”

10.0 out of 10, Exceptional, (24)
"Beautiful home. Tons of room. Beds everywhere. Didnt see in the add that it had a pool table in the basement! "
💙The Mountain Mama💛 Trail Riders “Home Away From Home”

Devil Anse Off Road Lodging Hatfield & McCoy Trail House

10.0 out of 10, Exceptional, (33)
"Great clean and easy place to stay. Would definitely return."
Devil Anse Off Road Lodging Hatfield & McCoy Trail House

Trailhouse66 is located in the heart of the Hatfield and McCoy feud territory.

9.8 out of 10, Exceptional, (9)
"The home was very clean and check in was easy. We enjoyed the fact that it was so close to the trails. Our stay was fairly short but would definitely stay here again!"
Trailhouse66 is located in the heart of the Hatfield and McCoy feud territory.

The Red Dog Chalet Couples Retreat w/ Hot Tub

9.2 out of 10, Wonderful, (5)
"Location and the red dog chalet is beautiful! Chalet is clean and cozy! Close to trails for riding. Host is very personable, wonderful and kind. We would love to come back one day! Highly recommend!"
The Red Dog Chalet Couples Retreat w/ Hot Tub

Turkey Creek Retreats

10.0 out of 10, Exceptional, (24)
"The location of this home was so conveniently located for us. It was spacious and just what we needed!"
Turkey Creek Retreats

Mountain Laurel House

10.0 out of 10, Exceptional, (39)
"It was a really nice modern cabin. They supplied all kitchen utensils and towels so you don't have to bring much"
Mountain Laurel House

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

9.8 out of 10, Exceptional, (12)
"Wonderful and inviting host! "
A & B TRAIL HOUSE @ Hatfield-McCoy Trails, 5 Beds Plus and 2 Baths

Devil Anse ATV Lodging

9.6 out of 10, Exceptional, (67)
"Came down with my son and Dad it was awesome definitely will be back!"
Devil Anse ATV Lodging

New 3 Bdrm unit w/ great location & ex. amenities

9.6 out of 10, Exceptional, (12)
"We came to Pikeville for our wedding shower and had such an amazing time at this property! It was very clean and had everything we needed. Would definitely recommend! "
The price is AU$423
includes taxes & fees
26 Nov - 27 Nov
New 3 Bdrm unit w/ great location & ex. amenities

Hatfield McCoy Trails, Buffalo Mountain. 1/2 mile to Devil Anse, Buffalo trail

9.6 out of 10, Exceptional, (10)
"Had a great time. Was the perfect location. Very. Close to trails and restaurants and gas station. Perfect place for two people and plenty of room for two couples"
The price is AU$298
includes taxes & fees
1 Dec - 2 Dec
Hatfield McCoy Trails, Buffalo Mountain. 1/2 mile to Devil Anse, Buffalo trail

Hokie Hideout at Billy Goat Mountain Village

10.0 out of 10, Exceptional, (19)
"Nice place to stay. Owner was nice snd friendly and showed me around. This was our first trip to the Hatfield McCoy trails and even though it rained the whole time. We still had a blast"
Hokie Hideout at Billy Goat Mountain Village

'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!

10.0 out of 10, Exceptional, (16)
"Lovely home that easily accommodated our little family gathering. Perfect place for us to be together after 6 long years!"
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!

Ryder's Retreat overlooking the city of Williamson!

8.8 out of 10, Excellent, (5)
"The owner was very quick at responding, and willing to alleviate any concerns immediately. The property was very clean and well taken care of. The inside had many cosmetic upgrades. There were a few minor broken things (toilet paper holder broketoilet lidtttoilet lid"
The price is AU$542
includes taxes & fees
27 Nov - 28 Nov
Ryder's Retreat overlooking the city of Williamson!

Appalachian Hideaways

8.8 out of 10, Excellent, (3)
"I reserved this place for employees we had working in the area. This place was perfect for their needs. They each had their own bedroom and bathroom, add in the comforts of home and it was the perfect place for them to relax after a long days work. Everything was clean, check in was easy, wifi worked great. The host is excellent! We communicated back and forth several times. She is exceptionally responsive and informative."
Appalachian Hideaways
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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Other types of properties in Pilgrim you may be interested in

The Landmark Hotel

3.5 star property
8.4 out of 10, Very good, (764)
"Came down to Pikeville to see Jeff Dunham's Comedy Show and had a blast. Motel is located just a few blocks from the venue, so it was very convenient. The bed was very comfortable too. Staff was very nice."
The price is AU$157
includes taxes & fees
26 Nov - 27 Nov
The Landmark Hotel

Hampton Inn Pikeville

2.5 star property
9.2 out of 10, Wonderful, (451)
"Front desk staff were very helpful."
The price is AU$208
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn Pikeville

Ramada Hotel & Conference Center by Wyndham Paintsville

2.5 star property
8.8 out of 10, Excellent, (438)
"It’s a lot bigger than it looks. The atrium is beautiful and so nicely decorated for the holidays. A couple had a beautiful wedding the day we were there."
The price is AU$172
includes taxes & fees
1 Dec - 2 Dec
Ramada Hotel & Conference Center by Wyndham Paintsville
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails: This holiday home rental outside of Pilgrim is located in the city centre, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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 Loretta Lynn's Birthplace - Butcher Hollow and Loretta Lynn's Home.

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.