Chestnut Hill Vacation Packages

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Top Chestnut Hill Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Element by Marriott Arundel Mills BWI Airport

Element by Marriott Arundel Mills BWI Airport

3 out of 5
Arundel Mills
Price was CA $1,616, price is now CA $1,086 per person
CA $1,086
per person
Sep 19 - Sep 24
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

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was CA $1,725, price is now CA $1,153 per person
CA $1,153
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.4/10 Very good! (2,841 reviews)
The fitness center is disappointing. Staff were very friendly. Lobby area is impressive. Location was good.

Reviewed on Jul 8, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Price was CA $2,096, price is now CA $1,403 per person
CA $1,403
per person
Sep 17 - Sep 21
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.6/10 Exceptional! (81 reviews)
The staff made the trip feel like I was welcomed and mattered! Absolutely would recommend!

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 $1,670, price is now CA $1,126 per person
CA $1,126
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
6/10 (1 review)

Hotel Indigo Baltimore Downtown by IHG

Hotel Indigo Baltimore Downtown by IHG

4 out of 5
Mount Vernon
Price was CA $1,858, price is now CA $1,307 per person
CA $1,307
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
9.2/10 Wonderful! (1,040 reviews)
I really appreciate the fact that it was a 24 hour hotel, because the train I took to Baltimore was extremely late. Staff was very helpful and I was able to head to bed right away.

Reviewed on Jul 7, 2026

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Chestnut Hill Hotel Deals

Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

2 out of 5
1240 Chesapeke Overlook Parkway Perryville MD
The price is CA $280 per night from Jul 21 to Jul 22
CA $280
CA $313 total
Jul 21 - Jul 22
includes taxes & fees
8.8/10 Excellent! (253 reviews)
"Y"

Reviewed on Jul 5, 2026

Great Wolf Lodge Perryville
Comfort Inn Towson - Baltimore North

Comfort Inn Towson - Baltimore North

2.5 out of 5
8801 Loch Raven Blvd Parkville MD
Fully refundable
The price is CA $95 per night from Aug 2 to Aug 3
CA $95
CA $110 total
Aug 2 - Aug 3
includes taxes & fees
6/10 (1,015 reviews)
"It was good very quiet location"

Reviewed on Jul 5, 2026

Comfort Inn Towson - Baltimore North
Holiday Inn Express Towson - Baltimore North by IHG

Holiday Inn Express Towson - Baltimore North by IHG

2.5 out of 5
1100 Cromwell Bridge Rd Towson MD
The price is CA $149 per night from Jul 19 to Jul 20
CA $149
CA $174 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (1,145 reviews)
"Very convenient directly off the highway. Fairly good breakfast with many food options in area. Clean rooms with good temperature control. A little pricey but what's not. Will stay again."

Reviewed on Jul 8, 2026

Holiday Inn Express Towson - Baltimore North by IHG
See all 232 properties in Chestnut Hill
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 Chestnut Hill vacation package cost?
You'll find cheap prices from CA $1,086 on Expedia for your Chestnut Hill escape. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Chestnut Hill costs.
What are the cheapest months to go to Chestnut Hill?
You can typically find reduced prices and greater availability in January, February and November. Check out our cheap Chestnut Hill vacation packages and you could score some great off-season discounts.
How many days is enough for Chestnut Hill?
The ideal duration for your Chestnut Hill vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to visit all the major attractions and discover some hidden spots along the way.
How to find the best Chestnut Hill package deals?
Use Expedia's filter tool to help you find some of the best Chestnut Hill package deals. When you begin 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 adventure for midweek, or look for Chestnut Hill package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chestnut Hill vacation as a package?
You can enjoy significant savings on your Chestnut Hill getaway by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chestnut Hill?
Score amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Chestnut Hill escape.
How to plan a trip to Chestnut Hill?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Chestnut Hill.
  2. Plan your budget wisely: Besides the cost of your stay, you should consider other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Chestnut Hill.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you'd like to experience in Chestnut Hill. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Chestnut Hill vacation package.

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