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Top Holiday Rentals in Pilgrim

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

10.0 out of 10, Exceptional, (3)
"Excellent service, very friendly"
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace

*The Decked out Den*

9.8 out of 10, Exceptional, (9)
"Great place to stay! Close to trails and all the Hatfield & McCoy history. Our favorite things were having a washer & dryer, fabulous fire pit area, we cooked on the Blackstone everyday, garage to park our side by sides in and the extra fridge in the garage for beverages! Updated, nice decor, plenty of deck space for enjoying the weather. Owners were very nice and checked in to make sure everything was going well. Would definitely recommend and would definitely stay there again!"
The price is £226
includes taxes & fees
6 Jul - 7 Jul
*The Decked out Den*

NEW PARADISE RETREAT - Hatfield Mccoy Trails - Rent 1-3 Cabins, Sleep up to 18

10.0 out of 10, Exceptional, (10)
"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

Appalachian Hideaways

8.8 out of 10, Excellent, (5)
"Cabin is nice and host was very nice and helpful only complaint was the train near the cabin was loud at times but would stay again."
Appalachian Hideaways

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

10.0 out of 10, Exceptional, (23)
"It was a great place to stay. We ride electric bikes. There were quite a few trails with easy access available. House was wonderful to stay in. Very neat and tidy."
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!

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 £239
includes taxes & fees
26 Jun - 27 Jun
Ryder's Retreat overlooking the city of Williamson!

Cute Little Whole House For Rent<br>Franklin’s Lodge

9.0 out of 10, Wonderful, (28)
"Great communication and supplied our needs"
Cute Little Whole House For Rent<br>Franklin’s Lodge

The Nook in Downtown Pikeville

8.0 out of 10, Very good, (2)
"This was a super convenient location for us to walk to a concert for a quick getaway. The nook was exactly as described and very clean. Would stay there again. "
The price is £137
includes taxes & fees
26 Jun - 27 Jun
The Nook in Downtown Pikeville

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

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

9.6 out of 10, Exceptional, (21)
"Beautiful house"
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails

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!

Creekside Lodge: 10 Sec Ride to Trail, Sleeps 10!

9.2 out of 10, Wonderful, (27)
"Place was very clean and had alot of parking for trailers. Close to trails and town, would definitely come back "
Creekside Lodge: 10 Sec Ride to Trail, Sleeps 10!

Trailhead Riverfront Cabin

10.0 out of 10, Exceptional, (2)
"Always a wonderful stay "
Trailhead Riverfront Cabin

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

10.0 out of 10, Exceptional, (28)
"Nice place to stray close to town and close to the utv trails! Enjoyed our stay!"
💙The Mountain Mama💛 Trail Riders “Home Away From Home”

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

9.6 out of 10, Exceptional, (5)
The price is £231
includes taxes & fees
13 Jul - 14 Jul
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access

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

9.6 out of 10, Exceptional, (15)
"We travel often from SC to OH and stay the night half way in Pikeville. We used to stay in the Hampton Inn, but we found this gem VRBO about a year ago. The location is great, super clean, and very cool. Thx for giving us this option Amelia. 5 stars! "
The price is £201
includes taxes & fees
26 Jun - 27 Jun
New 3 Bdrm unit w/ great location & ex. amenities

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.

Walking distance to gas station/riding passes, and the famous Sherry Bo’s diner

9.6 out of 10, Exceptional, (5)
"Everything was wonderful, made traveling to a family reunion easy."
The price is £126
includes taxes & fees
28 Jun - 29 Jun
Walking distance to gas station/riding passes, and the famous Sherry Bo’s diner

Tranquil 2-bedroom apartment in McDowell with AC, WiFi

The price is £136
includes taxes & fees
6 Jul - 7 Jul
Tranquil 2-bedroom apartment in McDowell with AC, WiFi

Luxury Estate nestled atop stunning mountaintop golf course!

2.0 star property
10.0 out of 10, Exceptional, (3)
"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!
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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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 The Coal House.

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.