Pilgrim Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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Top hotels in Pilgrim

The Landmark Hotel

The Landmark Hotel

3.5 out of 5
190 S Mayo Trail Pikeville KY
Fully refundableReserve now, pay when you stay
The price is S$132 per night from 7 Aug to 8 Aug
S$132
7 Aug - 8 Aug
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Front desk super nice. Fourth floor restaurant was great. Bed was amazing perfect soft and firmness."

Reviewed on 11 Jul, 2026

The Landmark Hotel
Ramada Hotel & Conference Center by Wyndham Paintsville

Ramada Hotel & Conference Center by Wyndham Paintsville

2.5 out of 5
624 James Trimble Blvd Paintsville KY
Fully refundableReserve now, pay when you stay
The price is S$172 per night from 27 Jul to 28 Jul
S$172
27 Jul - 28 Jul
includes taxes & fees
8.8/10 Excellent! (593 reviews)
"It was a really nice place to stay and very quiet"

Reviewed on 12 Jul, 2026

Ramada Hotel & Conference Center by Wyndham Paintsville
Days Inn by Wyndham Paintsville

Days Inn by Wyndham Paintsville

2 out of 5
512 S Mayo Trail Paintsville KY
Fully refundableReserve now, pay when you stay
The price is S$109 per night from 15 Jul to 16 Jul
S$109
15 Jul - 16 Jul
includes taxes & fees
7.6/10 Good! (559 reviews)
"Clean as always and very effortless check in as always.50plus year customer."

Reviewed on 4 Jul, 2026

Days Inn by Wyndham Paintsville
See all 185 properties in Pilgrim
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.

Frequently asked questions

How much does a Pilgrim holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday to Pilgrim costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Pilgrim?
January, February and August are great times to search for cheap Pilgrim holiday packages. Opting to travel in less busy months means you can usually find reduced prices on hotels and flights.
How many days is enough for Pilgrim?
The ideal length for your Pilgrim holiday depends on what you'd like to do. Usually, a handful of days to a week will give you plenty of time to hit all the leading attractions and discover some hidden treasures along the way.
How to find the best Pilgrim package deals?
Use Expedia's filter tool to help you find some great Pilgrim package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Pilgrim package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Pilgrim holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still have the flexibility to create a customised Pilgrim holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Pilgrim?
If you've got your Pilgrim holiday dates locked in, book early to snap up some outstanding deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Pilgrim?

  1. Choose when to get away: Check your diary and get your bags packed. Your favourite season and the activities on offer will also help you decide when to holiday in Pilgrim.
  2. Budget wisely: As well as the price of your hotel, you'll need to factor in other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that may arise during your trip to Pilgrim.
  3. Decide how long to go away for: Now that you're up to speed on Pilgrim, you can work out the right length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to see.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Pilgrim holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.