Holiday Rentals in Pilgrim

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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

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

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

Eccentric Privy-Sleeps6. 2nd floor & outdoor deck

9.0 out of 10, Wonderful, (4)
"Walkable to downtown"
Eccentric Privy-Sleeps6. 2nd floor & outdoor deck

Appalachian Hideaways

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

Country Charm

10.0 out of 10, Exceptional, (37)
"Second time staying at the cabin. We had a blast! Awesome place to stay. "
Country Charm

Trailside Lodge | 10 Sec to Trail, Hot Tub + Fire Pit

10.0 out of 10, Exceptional, (3)
"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

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

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

9.8 out of 10, Exceptional, (10)
"Clean and comfortable. "
The price is €180
includes taxes & fees
7 Sept - 8 Sept
Papa Bear's Den!! “The perfect location to visit the trails”

Ryder's Retreat overlooking the city of Williamson!

8.8 out of 10, Excellent, (5)
"One end of the neighborhood is sketch, other end is nice. People were nice to us in both ends."
The price is €364
includes taxes & fees
1 Oct - 2 Oct
Ryder's Retreat overlooking the city of Williamson!

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

Nice private home in Matewan, close to trails! Hottub, Pool, fire pits & games!

4.0 out of 10, (1)
"It' not worth it. I wish I would have heeded the negative reviews. "
The price is €393
includes taxes & fees
30 Sept - 1 Oct
Nice private home in Matewan, close to trails! Hottub, Pool, fire pits & games!

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

9.8 out of 10, Exceptional, (30)
"We had a good time staying here."
Hatfield McCoy Trails! Newly renovated 3 bedroom house with ATV trail access.

Luxury Estate nestled atop stunning mountaintop golf course!

2.0 star property
10.0 out of 10, Exceptional, (6)
"Everything was perfect from the booking to checkout. My husband and I live out of state but wanted to host our family and friends. This property exceeded expectations! The home was spacious and decorated beautifully for Christmas. It was both clean and well stocked with supplies. There is also plenty of parking. I highly recommend!"
Luxury Estate nestled atop stunning mountaintop golf course!

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

9.8 out of 10, Exceptional, (6)
"This location was perfect for our big group! "
The price is €255
includes taxes & fees
2 Sept - 3 Sept
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access

SMUGGLERS RUN: Cozy Cabin, quick & easy access to Hatfield-McCoy trail heads.

8.4 out of 10, Very good, (5)
"Very nice and clean cabin. Only have a 4 for the listing because I didn't see a hot tub."
SMUGGLERS RUN: Cozy Cabin, quick & easy access to Hatfield-McCoy trail heads.

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

10.0 out of 10, Exceptional, (12)
"Nice clean house really enjoyed it"
Trailhouse66 is located in the heart of the Hatfield and McCoy feud territory.

Spacious 4-bedroom house with all the extra amenities you’re looking for!

10.0 out of 10, Exceptional, (1)
"Best stay we have had in this area! Very responsive and helpful host!"
Spacious 4-bedroom house with all the extra amenities you’re looking for!

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 €165
includes taxes & fees
2 Sept - 3 Sept
Walking distance to gas station/riding passes, and the famous Sherry Bo’s diner

The Red Dog Cottage In The Woods w/ Hot Tub

10.0 out of 10, Exceptional, (39)
"This is an amazing place! Such a wonderful idea for rental property. We will be back! Pictures don’t do it justice! "
The Red Dog Cottage In The Woods w/ Hot Tub
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, apart-hotels, 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 €165 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?

Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking! : This holiday home rental outside of Pilgrim is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a patio and a garden.

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 Roy Collier Community Center and Williamson Memorial Fieldhouse.

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.