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

The stress-free way to experience this city is with a tailor-made Cheltenham vacation package. Base yourself in the neighborhood of Old Town Alexandria, which is great for walking, gift and craft shops and cafes or choose someplace else — our packages are all about you. Rosaryville State Park is just one of the must-see attractions to check off your itinerary during a trip to Cheltenham. Expedia is here to help you escape the everyday. Tailor your vacation to Cheltenham to match your travel style, whatever that may look like.

Top Cheltenham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Price was CA $859, price is now CA $622 per person
CA $622
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,006 reviews)
Nice location with friendly staff. The hotel is a bit dated and the rooms were too dark for my taste. The fitness center was extremely hot - I had to leave, you cannot adjust the thermostat and the fan is fixed and falling apart. Otherwise the room was large and comfortable, beds were nice, and the bathroom was great, but they could use some anti-slip assistance on the shower floor. Overall I liked it and would stay again.

Reviewed on Jul 10, 2026

Element by Marriott Arundel Mills BWI Airport

Element by Marriott Arundel Mills BWI Airport

3 out of 5
Arundel Mills
Price was CA $1,754, price is now CA $1,142 per person
CA $1,142
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8/10 Very good! (1,003 reviews)
Didn’t like that room service wasn’t available during my visit. Other than that the location was perfect!

Reviewed on Jul 5, 2026

Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Price was CA $1,808, price is now CA $1,237 per person
CA $1,237
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
6/10 (1 review)

Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Price was CA $1,363, price is now CA $963 per person
CA $963
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.6/10 Excellent! (1,002 reviews)
This was the first holiday inn that did not have breakfast. The information said breakfast available. We all assumed that it was the usual breakfast found at most holiday inns. The room also had only superficial cleaning.

Reviewed on Jul 10, 2026

Super 8 By Wyndham Baltimore Northwest

Super 8 By Wyndham Baltimore Northwest

2 out of 5
Woodlawn
Price was CA $1,485, price is now CA $1,081 per person
CA $1,081
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.2/10 Very good! (1,055 reviews)
Good staff and well maintained rooms.

Reviewed on Jul 10, 2026

Ready to book your vacation to Cheltenham?

 

Choose your dates

Cheltenham Hotel Deals

Washington Plaza Hotel

Washington Plaza Hotel

4 out of 5
10 Thomas Circle NW Washington DC
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Aug 3 to Aug 4
CA $154
CA $179 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (5,287 reviews)
"First of all this is a great value hotel. I choose this hotel as often as possible as the price point is lower than most of the newer hotels. It was probably a fancy place back in the day but it’s showing its age. If they redid the bathrooms and made the doors a little more high quality (they’re ..."

Reviewed on Jul 11, 2026

Washington Plaza Hotel
Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
1001 14th St NW Washington DC
The price is CA $164 per night from Aug 3 to Aug 4
CA $164
CA $233 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (3,498 reviews)
"Everything about my stay was exceptional except checkin. I requested early checkin. Nothing was available, and I left my cell number in case a room was found. I spent the next hour in the lobby watching person after person check in. Finally, I returned to the desk and a room was then found for me. ..."

Reviewed on Jul 10, 2026

Hamilton Hotel Washington DC
Omni Shoreham Hotel Washington DC

Omni Shoreham Hotel Washington DC

4 out of 5
2500 Calvert St Nw Washington DC
The price is CA $191 per night from Jul 18 to Jul 19
CA $191
CA $271 total
Jul 18 - Jul 19
includes taxes & fees
9/10 Wonderful! (2,406 reviews)
"Pool area is great"

Reviewed on Jul 9, 2026

Omni Shoreham Hotel Washington DC
See all 5,022 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 Tennis Courts

Catch an event at Cheltenham Tennis Courts during your trip to Rosaryville. Take in the festivals and mountain views in the area.
See properties

What to do in Cheltenham

Discover Alexandria: Historic Homes, Churches, and Taverns!

Discover Alexandria: Historic Homes, Churches, and Taverns!

CA $43
per adult
92% of travellers recommend
Discover Alexandria: Historic Homes, Churches, and Taverns!
George Washington's Mount Vernon Gardens & Grounds Admission

George Washington's Mount Vernon Gardens & Grounds Admission

CA $43
per adult
George Washington's Mount Vernon Gardens & Grounds Admission
Alexandria: American Revolution Guided Walking Tour

Alexandria: American Revolution Guided Walking Tour

CA $43
per adult
100% of travellers recommend
Alexandria: American Revolution Guided Walking Tour
See all activities in Cheltenham

Frequently asked questions

How much does a Cheltenham vacation package cost?
You can pick up a vacation package to this top destination from CA $622 on Expedia. However, how much your vacation to Cheltenham costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Cheltenham?
If you'd like to score a cheap Cheltenham vacation package, consider visiting in January, February and November. You'll typically find better rates on airfares and hotels during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Cheltenham?
The ideal duration for your Cheltenham vacation depends on what you'd like to do. Generally, a handful of days to a week will give you plenty of time to visit all the leading attractions and explore some hidden treasures along the way.
How to find the best Cheltenham package deals?
Use Expedia's filter tool to help you find some tempting Cheltenham package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Cheltenham package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Cheltenham vacation as a package?
You can enjoy significant savings on your next Cheltenham escape by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a great-value 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?
Secure fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Cheltenham getaway.
How to plan a trip to Cheltenham?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Cheltenham.
  2. Budget wisely: As well as the cost of your stay, you should consider other expenses too. These include food, transportation and flights. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Cheltenham.
  3. Decide your trip length: Think about how much time you'd like to spend exploring Cheltenham. Plan your days 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 place, you can combine your car rental, flights, hotels and more into a customized Cheltenham 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.