Pilgrim holiday rentals

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:1 Jan - 8 Jan

Interior
Living area
Interior
Interior
Exceptional
(30 reviews)

The Red Dog Chalet Couples Retreat w/ Hot Tub

Williamson

8% off
AU$1,942
for 7 nights, 1 chalet
AU$277 per night
includes taxes & fees
The Red Dog Chalet Couples Retreat w/ Hot Tub
Exterior detail
Living area
Room
Outdoor dining
Exceptional
(13 reviews)

Backwoods Bungalow

Pikeville

21% off
AU$1,448
for 7 nights, 1 cabin
AU$207 per night
includes taxes & fees
Backwoods Bungalow
Room
Exterior detail
Air-fryer & Mini Fridge
Coin-operated - Detergent provided
Exceptional
(5 reviews)

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

Lenore

8% off
AU$4,379
for 7 nights, 1 apartment
AU$626 per night
includes taxes & fees
NEW Entire Build 4 Studio Units by Outlaws - Sleeps 15! 4 BR/ 4BA Suites 9 Beds
Interior
Outdoor dining
Room
Private kitchen
Exceptional
(9 reviews)

Modern Escape

Pikeville

17% off
AU$1,249
for 7 nights, 1 home
AU$178 per night
includes taxes & fees
Modern Escape
Room
Living area
Interior
Exterior
Exceptional
(50 reviews)

The Red Dog Cottage In The Woods w/ Hot Tub

Williamson

8% off
AU$2,740
for 7 nights, 1 cottage
AU$391 per night
includes taxes & fees
The Red Dog Cottage In The Woods w/ Hot Tub
Outdoor dining
Living area
Interior
Interior
Wonderful
(9 reviews)

Inspiration Station

Pikeville

26% off
AU$1,373
for 7 nights, 1 cabin
AU$196 per night
includes taxes & fees
Inspiration Station
Rogers Park at TRC. B-ball court and playground
The Coal House aka Chamber of Commerce in Williamson WV
Master bedroom offers 2 large queen size beds
Property grounds
Exceptional
(37 reviews)

Turkey Creek Retreats

Belfry

8% off
AU$1,723
for 7 nights, 1 home
AU$246 per night
includes taxes & fees
Turkey Creek Retreats
Property grounds
Private kitchen
Room
Dining
Exceptional
(35 reviews)

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

Chattaroy

8% off
AU$3,271
for 7 nights, 1 home
AU$467 per night
includes taxes & fees
💙The Mountain Mama💛 Trail Riders “Home Away From Home”
Room
Outdoor dining
Living area
Exterior
Wonderful
(7 reviews)

Ryder's Retreat overlooking the city of Williamson!

Williamson

8% off
AU$2,360
for 7 nights, 1 home
AU$337 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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Pilgrim holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Pilgrim to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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