Dennis Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Martin Tucker

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    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

Your Dennis Vacation

With a vacation package to Dennis, say goodbye to endless planning and hello to trouble-free adventure. Every detail of your escape has been taken care of before you depart, so you can enjoy each moment experiencing this interesting city. During your trip to Dennis, give yourself plenty of time for sightseeing. An excellent place to begin is Tishomingo State Park. Whoever you're heading away with and whatever you want to spend, your ultimate Dennis vacation is just clicks away with Expedia.

Top Dennis Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Olive Branch by IHG

Holiday Inn Express & Suites Olive Branch by IHG

2.5 out of 5
Price was CA $980, price is now CA $937 per person
CA $937
per person
Jan 7 - Jan 11
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tupelo (TUP)
8.6/10 Excellent! (1,003 reviews)
No thank you.

Reviewed on Oct 29, 2026

Historic Whispering Woods Hotel & Conference Center

Historic Whispering Woods Hotel & Conference Center

3 out of 5
Price was CA $1,243, price is now CA $1,148 per person
CA $1,148
per person
Jan 7 - Jan 11
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tupelo (TUP)
7.2/10 Good! (1,000 reviews)
Staff was helpful and nice. Rooms clean

Reviewed on Oct 29, 2026

Candlewood Suites Olive Branch by IHG

Candlewood Suites Olive Branch by IHG

2.5 out of 5
Price was CA $988, price is now CA $944 per person
CA $944
per person
Jan 7 - Jan 11
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tupelo (TUP)
8/10 Very good! (199 reviews)
Very clean and nice accommodations. Check in was a breeze. I'd recommend this hotel over any in this area!

Reviewed on Oct 27, 2026

Hotel DeSoto

Hotel DeSoto

2.5 out of 5
Price was CA $995, price is now CA $956 per person
CA $956
per person
Jan 7 - Jan 11
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tupelo (TUP)
8.8/10 Excellent! (1,005 reviews)

GLō Best Western Olive Branch

GLō Best Western Olive Branch

2.5 out of 5
Price was CA $1,042, price is now CA $1,013 per person
CA $1,013
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tupelo (TUP)
9.6/10 Exceptional! (13 reviews)

Ready to book your vacation to Dennis?

 

Choose your dates

Dennis Hotel Deals

Holiday Inn Express Hotel & Suites Fulton by IHG

Holiday Inn Express Hotel & Suites Fulton by IHG

2.5 out of 5
1505 S. Adams St Fulton MS
Fully refundable
The price is CA $127 per night from Nov 29 to Nov 30
CA $127
CA $140 total
Nov 29 - Nov 30
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Very nice. We were told they are about to under go a complete refurbishment."

Reviewed on Oct 26, 2026

Holiday Inn Express Hotel & Suites Fulton by IHG
Heritage PLACE HOTEL IUKA

Heritage PLACE HOTEL IUKA

2.5 out of 5
1409 HERITAGE DRIVE IUKA MISS, 38852 Iuka MS
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Nov 26 to Nov 27
CA $110
CA $120 total
Nov 26 - Nov 27
includes taxes & fees
Heritage PLACE HOTEL IUKA
Best Inn Booneville

Best Inn Booneville

2.5 out of 5
805 N 2nd St Booneville MS
Fully refundableReserve now, pay when you stay
The price is CA $69 per night from Nov 29 to Nov 30
CA $69
CA $76 total
Nov 29 - Nov 30
includes taxes & fees
6.8/10 (334 reviews)
"Alot of sketchy individuals hanging out in the parking lot"

Reviewed on Oct 28, 2026

Best Inn Booneville
See all 79 properties in Dennis
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Dennis vacation package cost?
You'll find cheap prices from CA $937 on Expedia for your Dennis break. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Dennis costs.
What are the cheapest months to go to Dennis?
The off-season is the best time to head to Dennis if you're on a budget. Another tip for scoring cheap Dennis vacation packages? Try to avoid visiting during public holidays and any major festivals or events.
How many days is enough for Dennis?
With a well-planned itinerary, you can easily tick off the top Dennis sights in a few days. But if you prefer to venture off the beaten track or go on day trips, consider booking your Dennis vacation for longer.
How to find the best Dennis package deals?
Use Expedia's filters to find some unbeatable Dennis package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Dennis package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Dennis vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still get the freedom to create a customized Dennis vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Dennis?
If you're considering a spur-of-the-moment Dennis getaway, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Dennis?

  1. Pick your dates: What you'd like to do in Dennis and your preferred season will help you decide when to get away.
  2. Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to activities and flights. Your hotel will probably be the largest expense during your trip to Dennis.
  3. Decide how long to go away for: Now that you're more familiar with Dennis, you can work out the ideal length of your vacation. Pull together a rough itinerary and give yourself enough time to cover everything you want to do.
  4. Combine your accommodations and airfare: After you've settled on your travel dates and duration, lock in the perfect Dennis vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.