Ashland Vacation Packages

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Top Ashland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Jackson by IHG

Staybridge Suites Jackson by IHG

3 out of 5
Price was CA $613, price is now CA $583 per person
CA $583
per person
Aug 27 - Aug 29
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Jackson (JAN)
8.6/10 Excellent! (1,006 reviews)
The location was great and the breakfast was nice. However at check in, they gave us the wrong key and we opened another guest’s room. The next day, several guests including us got locked out of our suites. It took front staff at least 20 minutes to fix the problem. Our room was not as cleaned as we hoped. The floor in the kitchen had glue residue and water come out of it from between the tiles every time you step on them. The cushions on the couch smelled like dog pee.

Reviewed on Jul 17, 2026

Hilton Jackson

Hilton Jackson

3.5 out of 5
Price was CA $648, price is now CA $587 per person
CA $587
per person
Aug 27 - Aug 29
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Jackson (JAN)
7.6/10 Good! (1,010 reviews)
Hotel over book, room at the very top level and only one elevator working, roo m out dated and dirty, tv out, parking terrible, staff had no control over the business noise up to 3 am , when choosing stay on website Street view was not this location, false seen, over all horrible experience.

Reviewed on Jul 13, 2026

The Westin Jackson

The Westin Jackson

4 out of 5
Downtown Jackson
Price was CA $760, price is now CA $702 per person
CA $702
per person
Aug 27 - Aug 29
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Jackson (JAN)
9/10 Wonderful! (944 reviews)
We never received housekeeping service and after several requests, they brought us fresh towels and emptied the trash. The front desk staff didn't seem the least bit concerned and offered no apology.

Reviewed on Jul 8, 2026

Wingate by Wyndham Jackson/Ridgeland

Wingate by Wyndham Jackson/Ridgeland

3 out of 5
Price was CA $660, price is now CA $629 per person
CA $629
per person
Aug 27 - Aug 29
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Jackson (JAN)
7.6/10 Good! (1,018 reviews)

La Quinta Inn & Suites by Wyndham Jackson Airport/Pearl

La Quinta Inn & Suites by Wyndham Jackson Airport/Pearl

3 out of 5
Price was CA $627, price is now CA $603 per person
CA $603
per person
Aug 27 - Aug 29
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Jackson (JAN)
8.6/10 Excellent! (1,003 reviews)

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Ashland Hotel Deals

Natchez Grand Hotel & Suites On the River

Natchez Grand Hotel & Suites On the River

3 out of 5
111 S Broadway Street Natchez MS
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Jul 22 to Jul 23
CA $111
CA $160 total
Jul 22 - Jul 23
includes taxes & fees
8.6/10 Excellent! (1,626 reviews)
"Our stay at the Grand Hotel in Natchez was wonderful. The employees provided exceptional service from beginning to end. The concierge was incredibly helpful and truly a lifesaver during our stay. Judy, the housekeeping staff, and Ken, the driver, all went above and beyond to make us feel welcome ..."

Reviewed on Jul 16, 2026

Natchez Grand Hotel & Suites On the River
Magnolia Hotel, BW Signature Collection

Magnolia Hotel, BW Signature Collection

3.5 out of 5
645 S Canal Street Natchez MS
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Aug 4 to Aug 5
CA $130
CA $149 total
Aug 4 - Aug 5
includes taxes & fees
8.4/10 Very good! (1,005 reviews)
"Everything was horrible, the rooms were so outdated, terrible old stale odor."

Reviewed on Jul 16, 2026

Magnolia Hotel, BW Signature Collection
The Bridges Hotel

The Bridges Hotel

2.5 out of 5
10 Grand Soleil Blvd Natchez MS
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Jul 20 to Jul 21
CA $111
CA $128 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (204 reviews)
"The pool was not accessible due to issues, also requires a deposit that was not mentioned from the beginning. On top of that while inquiring about the deposit, management hung up the phone in my face.... hospitality of management was ridiculous, and no complementary breakfast."

Reviewed on Jul 17, 2026

The Bridges Hotel
See all 147 properties in Ashland
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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What to do in Ashland

Windsor Ruins Audio Experience

Windsor Ruins Audio Experience

CA $13
per adult
Windsor Ruins Audio Experience
See all activities in Ashland

Frequently asked questions

How much does an Ashland vacation package cost?
You'll find cheap prices from CA $583 on Expedia for your Ashland escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Ashland costs.
What are the cheapest months to go to Ashland?
You can usually find reduced prices and greater availability in January, February and November. Take a look at our cheap Ashland vacation packages and you could get some great off-season discounts.
How many days is enough for Ashland?
With a well-organized travel plan, you can easily hit the most popular Ashland attractions in a few days. But if you'd like to venture off the beaten track or take day trips, think about booking your Ashland vacation for longer.
How to find the best Ashland package deals?
Bagging a cheap Ashland package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Ashland package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book an Ashland vacation as a package?
You can enjoy significant savings on your Ashland retreat by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Ashland?
If you're planning an impromptu Ashland trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Ashland?

  1. Choose when to go: Check your diary and pack your bags. Your preferred season and the activities on offer will also help you decide when to visit Ashland.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and dining out to activities and flights. Your accommodations will probably be the biggest expense during your trip to Ashland.
  3. Decide your trip length: Think about how much time you'd like to spend discovering Ashland. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Ashland vacation package.

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.