Cheltenham Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • 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 Cheltenham Vacation

Book a Cheltenham vacation package and prepare to experience the highlights of this city. Consider basing yourself in the neighborhood of Old City, which is good for nightlife, culture and history. Fill your itinerary with visits to Temple University, Willow Grove Park Mall and The Liacouras Center, some of the top attractions you really should see during your trip to Cheltenham. Whoever you're heading away with and whatever your budget, your dream Cheltenham vacation is only clicks away with Expedia.

Top Cheltenham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Centric Rittenhouse Square Philadelphia

Hyatt Centric Rittenhouse Square Philadelphia

4 out of 5
Center City
Price was CA $1,403, price is now CA $1,131 per person
CA $1,131
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Philadelphia (PHL)
9.4/10 Exceptional! (1,790 reviews)

Tudor Lux

Tudor Lux

4 out of 5
Price was CA $4,313, price is now CA $2,992 per person
CA $2,992
per person
Dec 18 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philadelphia (PHL)
No reviews

Tudor Place

Tudor Place

4 out of 5
Price was CA $3,687, price is now CA $2,632 per person
CA $2,632
per person
Dec 18 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philadelphia (PHL)
No reviews

Orchard Way

Orchard Way

2 out of 5
Price was CA $2,916, price is now CA $2,133 per person
CA $2,133
per person
Dec 18 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philadelphia (PHL)
No reviews

The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

5 out of 5
Center City
Save 100% on your flight
Price was CA $3,701, price is now CA $2,856 per person
CA $2,856
per person
Dec 1 - Dec 8
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to Philadelphia (PHL)
9.4/10 Exceptional! (1,002 reviews)
The environment was serene. The hotel is exceptionally clean, and has arguable the best bathroom shower (no mold, no discolored tiles) I have seen - and I do stay in five-star resorts/hotels all the time. They have the most polite staff. The classical music played overhead at the lobby is very soothing.

Reviewed on Oct 25, 2026

Ready to book your vacation to Cheltenham?

 

Choose your dates

Cheltenham Hotel Deals

Club Quarters Hotel Rittenhouse Square, Philadelphia

Club Quarters Hotel Rittenhouse Square, Philadelphia

4 out of 5
1628 Chestnut St Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Nov 2 to Nov 3
CA $157
CA $182 total
Nov 2 - Nov 3
includes taxes & fees
Club Quarters Hotel Rittenhouse Square, Philadelphia
Doubletree by Hilton Philadelphia Airport

Doubletree by Hilton Philadelphia Airport

4 out of 5
4509 Island Ave Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Nov 26 to Nov 27
CA $144
CA $167 total
Nov 26 - Nov 27
includes taxes & fees
Doubletree by Hilton Philadelphia Airport
Motto by Hilton Philadelphia Rittenhouse Square

Motto by Hilton Philadelphia Rittenhouse Square

3.5 out of 5
31 S 19th St Philadelphia PA
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Nov 1 to Nov 2
CA $114
CA $132 total
Nov 1 - Nov 2
includes taxes & fees
Motto by Hilton Philadelphia Rittenhouse Square
See all 3,076 properties in Cheltenham
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

Stay near popular Cheltenham attractions

Cheltenham Center For The Arts

Enjoy an outing to Cheltenham Center For The Arts during your stay in Cheltenham. While you're in the area, wander around the gardens.
See properties

What to do in Cheltenham

LEGOLAND® Discovery Center Philadelphia

LEGOLAND® Discovery Center Philadelphia

CA $35
per adult
80% of travellers recommend
LEGOLAND® Discovery Center Philadelphia
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions

Go City: Philadelphia All-Inclusive Pass with 30+ Attractions

CA $83
per adult
82% of travellers recommend
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions
Double Decker Hop-On Hop-Off City Sightseeing Philadelphia

Double Decker Hop-On Hop-Off City Sightseeing Philadelphia (1, 2, or 3-Day)

CA $69
per adult
92% of travellers recommend
Double Decker Hop-On Hop-Off City Sightseeing Philadelphia (1, 2, or 3-Day)
See all activities in Cheltenham

Frequently asked questions

How much does a Cheltenham vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,131 on Expedia. However, how much your vacation to Cheltenham costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Cheltenham?
You can usually find lower rates and greater availability in January, February and March. Take a look at our cheap Cheltenham vacation packages and you could score some great off-season deals.
How many days is enough for Cheltenham?
With about 2 days, you'll have plenty of time to experience popular neighbourhoods like North Philadelphia East and North Philadelphia during your Cheltenham vacation. Be sure to also add Keswick Theatre and Morris Arboretum to your sightseeing list. Searching for more adventures? Consider exploring outside of Cheltenham on tours and day trips.
How to find the best Cheltenham package deals?
Landing a cheap Cheltenham package deal is a cinch with Expedia. Once you've entered your travel 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 "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Cheltenham package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Cheltenham vacation as a package?
You can enjoy significant savings on your next Cheltenham getaway by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view 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 Cheltenham?
If you've got your Cheltenham travel dates confirmed, book early to score some unbeatable deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Cheltenham?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Cheltenham.
  2. Calculate your budget: Make sure you have enough money to cover everything from meals and transportation to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Cheltenham.
  3. Set the duration of your trip: Start by compiling a list of the activities and attractions you want to experience in Cheltenham. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find a Cheltenham vacation package that brings all your bookings together.

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