Highland Vacation Packages

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Top Highland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Vandalia/Dayton International Airport

Super 8 by Wyndham Vandalia/Dayton International Airport

2 out of 5
per person
Aug 29 - Sep 1
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Dayton (DAY)
6.2/10 (973 reviews)
The staff were very nice

Reviewed on Jul. 22, 2025

Wingate by Wyndham Dayton - Fairborn

Wingate by Wyndham Dayton - Fairborn

2.5 out of 5
per person
Aug 29 - Sep 1
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Dayton (DAY)
8.2/10 Very Good! (1,005 reviews)
Room was good, clean but the office chair in the room was falling apart. Breakfast in the lobby was forgettable. I normally don't bother to rate the hotel breakfast because they are all forgettable. I only time i will bother with a breakfast review is if the hotel pairs with a restaurant within the hotel.

Reviewed on Jul. 24, 2025

Mills Park Hotel

Mills Park Hotel

3.5 out of 5
per person
Aug 29 - Sep 1
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Dayton (DAY)
9.8/10 Exceptional! (730 reviews)
Enjoyed our stay of 4 nights at Mills Park Hotel. The building has character, the staff are friendly. There is plenty of parking. The location in center of town is great - easy walk to interesting shops and restaurants. On site restaurant has good breakfast menu; we did not have dinner there because of other commitments.

Reviewed on Jul. 26, 2025

Days Inn by Wyndham Englewood Dayton Airport

Days Inn by Wyndham Englewood Dayton Airport

2 out of 5
per person
Aug 29 - Sep 1
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Dayton (DAY)
8.6/10 Excellent! (959 reviews)
The night clerk was absolutely amazing! She was just the kindest and seeetest and so friendly even though we checked in after

Reviewed on Jul. 25, 2025

Ready to book your vacation to Highland?

 

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Highland Hotel Deals

General Denver Hotel

General Denver Hotel

2 out of 5
81 W Main St, Wilmington, OH
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Jul 27 to Jul 28
CA $162
CA $183 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (128 reviews)
A Great Place to Stay in Wilmington
"Was pleasantly surprised how nice this place was. The staff was very helpful, and the restaurant had excellent food. It was only 4 miles from the World Equestrian Center and the Catholic Church was right across the street. I'm planning on staying there again next time I come back."

Reviewed on Jul. 7, 2025

General Denver Hotel
Holiday Inn Wilmington by IHG

Holiday Inn Wilmington by IHG

3 out of 5
123 Gano Rd, Wilmington, OH
Fully refundable
The price is CA $153 per night from Aug 3 to Aug 4
CA $153
CA $181 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (584 reviews)
HIGHLY Recommend!!
"Great Hotel! The customer service was excellent. The lobby was beautiful, cafe had great coffee and snacks and the staff was very helpful. Room was clean and so comfortable. Ralphs restaurant was very good and reasonably priced. I would highly recommend this Hotel!"

Reviewed on Jul. 21, 2025

Holiday Inn Wilmington by IHG
Fairfield Inn & Suites Jeffersonville I-71

Fairfield Inn & Suites Jeffersonville I-71

2.5 out of 5
11349 Allen Road NW, Jeffersonville, OH
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Aug 1 to Aug 2
CA $184
CA $208 total
Aug 1 - Aug 2
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Very nice place would definitely stay again."

Reviewed on Jul. 24, 2025

Fairfield Inn & Suites Jeffersonville I-71
See all 116 properties in Highland
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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Frequently asked questions

How much does a Highland vacation package cost?
Offering excellent value package deals from CA $775 on Expedia, you'll be pleasantly surprised at how much a vacation to Highland costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Highland?
If you're looking to book a cheap Highland vacation package, consider planning a trip in January, February and March. You'll generally find better rates on hotels and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Highland?
Typically, a handful of days is enough to tick off the top attractions during your Highland vacation. But if you prefer to have more time to kick back or take day trips, consider extending your itinerary.
How to find the best Highland package deals?
Bagging a cheap Highland package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Highland package deals. Want a simple trick to get 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 a Highland vacation as a package?
You can enjoy significant savings on your Highland escape by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Highland?
If you're considering a spontaneous Highland getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Highland?

  1. Pick your dates: What you want to do in Highland and your favourite season will help you decide when to travel.
  2. Plan your budget wisely: On top of the price of your stay, you should consider other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Highland.
  3. Decide how long to go away for: Now that you know more about Highland, you can figure out the right length of your break. Pull together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Highland vacation package.

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