Chestnut Hill Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Chestnut Hill

Comfort Inn Baltimore East Towson
Comfort Inn Baltimore East Towson
2.5 out of 5
8801 Loch Raven Blvd, Parkville, MD
Fully refundableReserve now, pay when you stay
The price is S$106 per night from 29 Jun to 30 Jun
S$106
29 Jun - 30 Jun
includes taxes & fees
6/10 (1,003 reviews)
"I was surprised how convenient it was to restaurants."

Reviewed on 14 Jun, 2025

Comfort Inn Baltimore East Towson
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
Fully refundable
The price is S$181 per night from 30 Jun to 1 Jul
S$181
30 Jun - 1 Jul
includes taxes & fees
8.8/10 Excellent! (1,021 reviews)
"Property was clean and staff was friendly and customer service oriented."

Reviewed on 17 Jun, 2025

Holiday Inn Express Towson - Baltimore North by IHG
Great Wolf Lodge Perryville
Great Wolf Lodge Perryville
2 out of 5
1240 Chesapeke Overlook Parkway, Perryville, MD
Fully refundableReserve now, pay when you stay
The price is S$287 per night from 24 Jun to 25 Jun
S$287
24 Jun - 25 Jun
includes taxes & fees
8.8/10 Excellent! (99 reviews)
"The cleaning staff went out of their way if I needed anything extra well appreciated"

Reviewed on 18 Jun, 2025

Great Wolf Lodge Perryville
See all 280 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.

Frequently asked questions

How much does a Chestnut Hill holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Chestnut Hill costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chestnut Hill?
January, February and November are great times to search for cheap Chestnut Hill holiday packages. Choosing to travel in quieter periods means you can usually find reduced prices on accommodation and flights.
How many days is enough for Chestnut Hill?
The ideal length for your Chestnut Hill holiday depends on what you'd like to see and do. Usually, a handful of days to a week will give you enough time to go to all the leading sights and explore some hidden spots along the way.
How to find the best Chestnut Hill package deals?
Use Expedia's handy filters to find some tempting Chestnut Hill package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Chestnut Hill package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your holiday package as soon as possible.
Is it cheaper to book a Chestnut Hill holiday as a package?
You can enjoy significant savings on your Chestnut Hill retreat by booking a customised holiday package. Check the "Package" heading, then select your travel dates and destination to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Chestnut Hill?
If you're planning an impromptu Chestnut Hill trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Chestnut Hill?

  1. Choose your dates: The things you want to do in Chestnut Hill and your favourite season will help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to pay for everything from food and transportation to experiences and flights. Your hotel will likely be the largest expense during your trip to Chestnut Hill.
  3. Set the duration of your trip: Start by making a list of all the attractions 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 car rental, hotels, flights and more into a personalised Chestnut Hill holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.