Pilgrim Vacation Rentals

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Sep 3 - Sep 4
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Sep 12 - Sep 14

Vacation Rentals in Pilgrim

Our top choices for Pilgrim vacation rentals

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

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
Fridge, microwave, oven, stovetop

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
Property grounds

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
Living area

Appalachian Hideaways

9.0 out of 10, Wonderful, (6)
"Great place "
Appalachian Hideaways
Country Charm
Fridge, microwave, oven, stovetop

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
Dining

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
Terrace/patio

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
Outdoor dining

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”
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (10)
"Clean and comfortable. "
The price is ￥13,246
￥30,319 total
includes taxes & fees
Sep 8 - Sep 9
Papa Bear's Den!! “The perfect location to visit the trails”
Ryder's Retreat overlooking the city of Williamson!
Fridge, microwave, stovetop, coffee/tea maker

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 ￥38,561
￥61,324 total
includes taxes & fees
Oct 1 - Oct 2
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
Exterior

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!
Smart TV, fireplace, foosball, table tennis

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 ￥35,482
￥66,819 total
includes taxes & fees
Sep 30 - Oct 1
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.
Fridge, microwave, oven, stovetop

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!
Interior

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
Property grounds

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 ￥24,726
￥44,402 total
includes taxes & fees
Sep 8 - Sep 9
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
SMUGGLERS RUN: Cozy Cabin, quick & easy access to Hatfield-McCoy trail heads.
Exterior

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.
Smart TV

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.
Walking distance to gas station/riding passes, and the famous Sherry Bo’s diner
Fridge, microwave, oven, stovetop

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 ￥15,101
￥27,452 total
includes taxes & fees
Sep 4 - Sep 5
Walking distance to gas station/riding passes, and the famous Sherry Bo’s diner
The Red Dog Cottage In The Woods w/ Hot Tub
2 bedrooms, free WiFi, bed sheets

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

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!
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

Search for holiday rentals in Pilgrim on Expedia! You can easily find your home rentals, villas, holiday apartments in Pilgrim using one of the methods below:

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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?

Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking! : This vacation home rental near Pilgrim is located in the mountains and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation 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 larger area, you’ll find Roy Collier Community Center and Williamson Memorial Fieldhouse.

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.