Pilgrim holiday homes

We found 59 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Pilgrim that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Pilgrim

Showing deals for:8 Jan - 15 Jan

Interior
Living area
Interior
Interior
Exceptional
(31 reviews)

The Red Dog Chalet Couples Retreat w/ Hot Tub

Williamson

8% off
NZ$2,396
for 7 nights, 1 chalet
NZ$342 per night
includes taxes & fees
The Red Dog Chalet Couples Retreat w/ Hot Tub
Room
Exterior detail
Coin-operated - Detergent provided
Exterior
Exceptional
(5 reviews)

NEW Entire Build 4 Studio Units by Outlaws - Sleeps 15! 4 BR/ 4BA Suites 9 Beds

Lenore

8% off
NZ$5,604
for 7 nights, 1 apartment
NZ$801 per night
includes taxes & fees
NEW Entire Build 4 Studio Units by Outlaws - Sleeps 15! 4 BR/ 4BA Suites 9 Beds
Living area
Living area
Interior
Room
Exceptional
(50 reviews)

The Red Dog Cottage In The Woods w/ Hot Tub

Williamson

8% off
NZ$3,385
for 7 nights, 1 cottage
NZ$484 per night
includes taxes & fees
The Red Dog Cottage In The Woods w/ Hot Tub
Interior
Outdoor dining
Private kitchen
Room
Exceptional
(9 reviews)

Modern Escape

Pikeville

16% off
NZ$1,262
for 7 nights, 1 home
NZ$180 per night
includes taxes & fees
Modern Escape
Property grounds
Private kitchen
Dining
Room
Exceptional
(35 reviews)

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

Chattaroy

8% off
NZ$4,115
for 7 nights, 1 home
NZ$588 per night
includes taxes & fees
💙The Mountain Mama💛 Trail Riders “Home Away From Home”
Property grounds
The Coal House aka Chamber of Commerce in Williamson WV
Living room offers a full size hideaway bed and fireplace.
Rogers Park at TRC. B-ball court and playground
Exceptional
(37 reviews)

Turkey Creek Retreats

Belfry

8% off
NZ$2,171
for 7 nights, 1 home
NZ$310 per night
includes taxes & fees
Turkey Creek Retreats
Interior
Living area
Outdoor dining
Room
Wonderful
(9 reviews)

Inspiration Station

Pikeville

25% off
NZ$1,500
for 7 nights, 1 cabin
NZ$214 per night
includes taxes & fees
Inspiration Station
Living area
Outdoor dining
Private kitchen
Room
Wonderful
(7 reviews)

Ryder's Retreat overlooking the city of Williamson!

Williamson

8% off
NZ$2,907
for 7 nights, 1 home
NZ$415 per night
includes taxes & fees
Ryder's Retreat overlooking the city of Williamson!

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Pilgrim getaway

Learn about the unique charm of Pilgrim with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Pilgrim

Are you hoping to find top things to see and do in the city? Venture out of your cosy holiday rental and check out everything that makes Pilgrim a fun spot to go on holiday. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • StoneCrest Golf Course (19.4 mi / 31.3 km)
  • Paintsville Golf Course (19.4 mi / 31.2 km)

Exploring the natural landscape of Pilgrim

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Pilgrim is a great spot to appreciate mother nature. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Hatfield McCoy Trail - Buffalo Mountain Trail System (13.6 mi / 21.8 km)
  • Jenny Wiley State Resort Park (18.2 mi / 29.3 km)
  • Preston Park (20.9 mi / 33.7 km)
  • Archer Park (21.9 mi / 35.2 km)
  • Rogers Park (10.5 mi / 16.9 km)
  • Laurel Creek State Wildlife Management Area (12.5 mi / 20.1 km)

How to get to and around Pilgrim

The nearest airport is in Pikeville, KY (PVL-Pike County - Hatcher Field), located 18.4 mi (29.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Pilgrim when booking a holiday rental?
When considering a holiday rental in Pilgrim, Kentucky, the nearby town of Paintsville is an excellent choice. This charming area offers a selection of properties that cater to various preferences, from quaint cottages to more spacious homes. Paintsville serves as a gateway to the scenic beauty of the region, providing a picturesque setting for your stay.One of the top attractions in Paintsville is the U.S. 23 Country Music Highway Museum, which celebrates the rich musical heritage of the area. Visitors can engage in the local culture and history, making it a delightful stop during your holiday. Additionally, the nearby Paintsville Lake State Park offers stunning vistas and opportunities for outdoor activities such as hiking, fishing, and boating, ensuring that nature enthusiasts will find plenty to enjoy.Another nearby option is the community of Van Lear, which is renowned for its historical significance and close-knit atmosphere. This area boasts a few rental properties and provides easy access to local attractions, including the famous Loretta Lynn's Ranch, which attracts fans of country music and offers a glimpse into the life of the legendary singer.Overall, both Paintsville and Van Lear offer a welcoming environment for holidaymakers, with a variety of properties to choose from and a host of attractions that highlight the unique charm of the region.
Are all fees included in the Pilgrim holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Pilgrim holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Pilgrim with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Pilgrim holiday homes?
You can find great discounts on holiday homes in Pilgrim on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Pilgrim holiday home booking on Bookabach?
To find Pilgrim holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Pilgrim?
A long-stay holiday home in Pilgrim is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Pilgrim holiday home?
Book your Pilgrim holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pilgrim?
Prices for holiday homes in Pilgrim vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Pilgrim to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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