Pensacola Vacation Packages

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Your Pensacola Vacation

Build a custom vacation package to Pensacola and prepare to experience this incredible city on your own terms. Think about staying in the neighborhood of Mountain Air, which is good for golfing and lots more. Make sure to do some sightseeing during your trip to Pensacola. Summit Trail and Parkway Playhouse are some well-known attractions to visit. Expedia is here to help you escape your daily routine. Tailor your vacation to Pensacola to suit your travel style, whatever that may be.

Top Pensacola Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Art of Living Retreat Center

Art of Living Retreat Center

3.5 out of 5
Price was CA $1,084, price is now CA $1,030 per person
CA $1,030
per person
Nov 7 - Nov 9
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Asheville (AVL)
8.2/10 Very Good! (60 reviews)
Hilton Garden Inn Asheville Downtown

Hilton Garden Inn Asheville Downtown

3 out of 5
Downtown Asheville
Price was CA $1,941, price is now CA $1,347 per person
CA $1,347
per person
Oct 14 - Oct 20
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Asheville (AVL)
9.2/10 Wonderful! (856 reviews)
Walking distance to downtown was very convenient.

Reviewed on Aug. 21, 2025

Kimpton Hotel Arras by IHG

Kimpton Hotel Arras by IHG

4 out of 5
Downtown Asheville
Price was CA $2,826, price is now CA $2,117 per person
CA $2,117
per person
Oct 17 - Oct 23
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Asheville (AVL)
9.6/10 Exceptional! (1,015 reviews)
Great hotel in great location. Front of house staff was exceptional. Bar staff unfortunately was quite rude and unfriendly. Maybe they were just understaffed, but don’t take that out on the customer.

Reviewed on Aug. 24, 2025

Four Points by Sheraton Asheville Downtown

Four Points by Sheraton Asheville Downtown

3 out of 5
Downtown Asheville
Price was CA $1,440, price is now CA $1,260 per person
CA $1,260
per person
Oct 14 - Oct 20
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Asheville (AVL)
8.4/10 Very Good! (1,004 reviews)
This property is endorsed by Sheraton but managed by a completely different company. Easy to walk into downtown Asheville. Bathroom and bedding were nice and clean.

Reviewed on Aug. 25, 2025

The Glamping Collective

The Glamping Collective

2 out of 5
Price was CA $2,758, price is now CA $2,563 per person
CA $2,563
per person
Oct 17 - Oct 23
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Asheville (AVL)
10/10 Exceptional! (13 reviews)
Really nice stay! Unique and fun glamping experience.

Reviewed on Jun. 27, 2025

Ready to book your vacation to Pensacola?

 

Choose your dates

Pensacola Hotel Deals

Super 8 by Wyndham Black Mountain

Super 8 by Wyndham Black Mountain

2 out of 5
101 Flat Creek Rd, Black Mountain, NC
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Sep 17 to Sep 18
CA $87
CA $99 total
Sep 17 - Sep 18
includes taxes & fees
8/10 Very Good! (491 reviews)
Mark
"Was very nice. Very accomodating. The free pet policy is wonderful. I love the Flat Creek!"

Reviewed on Aug. 20, 2025

Super 8 by Wyndham Black Mountain
Hampton Inn Black Mountain

Hampton Inn Black Mountain

2.5 out of 5
306 Black Mountain Avenue, Black Mountain, NC
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Sep 1 to Sep 2
CA $168
CA $190 total
Sep 1 - Sep 2
includes taxes & fees
Hampton Inn Black Mountain
Comfort Inn North of Asheville

Comfort Inn North of Asheville

2.5 out of 5
167 Jf Robinson Ln, Mars Hill, NC
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Aug 28 to Aug 29
CA $143
CA $160 total
Aug 28 - Aug 29
includes taxes & fees
8.6/10 Excellent! (701 reviews)
"Great staff!"

Reviewed on Jul. 25, 2025

Comfort Inn North of Asheville
See all 1,550 properties in Pensacola
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
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Family Vacations
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Discover the most popular places to visit in Pensacola

Mount Mitchell

Explore the great outdoors at Mount Mitchell and enjoy the mountain views during your trip to Burnsville. Take in the live music while you're in the area.

Mount Mitchell

Frequently asked questions

How much does a Pensacola vacation package cost?
Offering great value package deals from CA $1,030 on Expedia, you'll be surprised at how little a vacation to Pensacola costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Pensacola?
January, February and April are great times to look for cheap Pensacola vacation packages. Opting to travel in quieter months means you can generally find better prices on hotels and flights.
How many days is enough for Pensacola?
The ideal duration for your Pensacola vacation depends on what you'd like to do. Typically, a handful of days to a week will give you plenty of time to hit all the main attractions and explore some hidden gems along the way.
How to find the best Pensacola package deals?
Use Expedia's filters to help you find some of the best Pensacola package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Pensacola package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Pensacola vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can customize your Pensacola escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Pensacola?
If you've got your Pensacola vacation dates finalized, book as early as you can to bag some outstanding deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Pensacola?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Pensacola.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and activities. Your accommodations will probably be the largest expense during your trip to Pensacola.
  3. Decide how long to go for: Now that you're up to speed on Pensacola, you can figure out the perfect length of your vacation. Put together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Pensacola vacation package.

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