Pilgrim Holiday Rentals

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Holiday Rentals in Pilgrim

Our top choices for Pilgrim holiday rentals

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

9.8 out of 10, Exceptional, (11)
"Excellent service, very friendly"
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace

Appalachian Hideaways

9.0 out of 10, Wonderful, (6)
"Great place "
Appalachian Hideaways

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."
The price is NZ$320
includes taxes & fees
26 Sept - 27 Sept
Walking distance to gas station/riding passes, and the famous Sherry Bo’s diner

Turkey Creek Retreats

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

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

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

10.0 out of 10, Exceptional, (12)
"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

Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access

9.8 out of 10, Exceptional, (6)
"Loved the house had a great experience would definitely stay again"
The price is NZ$500
includes taxes & fees
29 Sept - 30 Sept
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access

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

8.8 out of 10, Excellent, (13)
"would stay here again "
Unit B: 20 Sec Ride to Trails, Sleeps 10. King

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

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

Devil Anse Off Road Lodging Hatfield & McCoy Trail House

10.0 out of 10, Exceptional, (43)
"Great place to stay!"
Devil Anse Off Road Lodging Hatfield & McCoy Trail House

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

10.0 out of 10, Exceptional, (11)
"Clean and comfortable. "
The price is NZ$424
includes taxes & fees
5 Oct - 6 Oct
Papa Bear's Den!! “The perfect location to visit the trails”

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 Cabin #2

9.4 out of 10, Exceptional, (10)
"Nice little spot to stay after a day riding the trails."
The price is NZ$342
includes taxes & fees
24 Sept - 25 Sept
Appalachian Hideaways Cabin #2

11 bed 7 bath large home and able to ride right from the home to the HMT trails

2.0 star property
10.0 out of 10, Exceptional, (1)
11 bed 7 bath large home and able to ride right from the home to the HMT trails

Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!

10.0 out of 10, Exceptional, (24)
"Great place to stay very easy trail access don’t even have to go on a main road. Very clean and a quiet place to stay. Would recommend to anyone! "
Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!

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”

10.0 out of 10, Exceptional, (5)
"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."
The price is NZ$352
includes taxes & fees
1 Oct - 2 Oct
Mama Bears den “The perfect location to visit the Hatfield and McCoy trails”

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!

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
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

Find out more about Pilgrim

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$320 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?

Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace: This holiday home rental outside of Pilgrim is located in the mountains, and has an indoor pool, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

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 Williamson Memorial Fieldhouse 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.