Pilgrim Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Pilgrim Vacation Packages

Pilgrim Hotel Deals

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 SARĀ 334 per night from Jul 17 to Jul 18
SARĀ 334
SARĀ 383 total
17 Jul - 18 Jul
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"The pool was nice,staff were great clean room and certainly had good air conditioning"

Reviewed on 15 July 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 SARĀ 444 per night from Aug 9 to Aug 10
SARĀ 444
SARĀ 489 total
9 Aug - 10 Aug
includes taxes & fees
8.8/10 Excellent! (594 reviews)
"This is a hidden gem in the mountains of EKY!"

Reviewed on 15 July 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 SARĀ 287 per night from Jul 19 to Jul 20
SARĀ 287
SARĀ 317 total
19 Jul - 20 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 July 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 vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Pilgrim costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Pilgrim?
You can typically find lower rates and better availability in January, February and August. Explore our cheap Pilgrim vacation packages and you could get some great off-season discounts.
How to find the best Pilgrim package deals?
Start your search for a Pilgrim package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Pilgrim package deal right away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Pilgrim getaway off to a flying start.
Is it cheaper to book a Pilgrim vacation as a package?
You can enjoy significant savings on your Pilgrim escape by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Pilgrim?
If you're considering a spontaneous Pilgrim adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Pilgrim?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Pilgrim.
  2. Set your budget: Factor in costs like flights, meals and transportation when working out how much to set aside for your trip to Pilgrim. Then, select a property that matches your budget, whether that's an affordable option or a more luxurious getaway.
  3. Decide your trip length: Consider how long you want to spend exploring Pilgrim. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Pilgrim vacation package that brings all your bookings together.