Chestnut Hill 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 Chestnut Hill Vacation

Take the hard work out of travel planning with a Chestnut Hill vacation package. A great neighborhood to base yourself in this amazing city is Swan Point, which is great for golfing and much more. Every trip to Chestnut Hill has to include a little sightseeing. Caledon State Park is a superb place to kick things off. Don't delay visiting this destination any longer. The ultimate Chestnut Hill vacation is only a few clicks away with Expedia.

Top Chestnut Hill Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Baltimore Downtown by IHG

Hotel Indigo Baltimore Downtown by IHG

4 out of 5
Mount Vernon
Price was CA $928, price is now CA $733 per person
CA $733
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.2/10 Wonderful! (1,134 reviews)
Lost my phone charger and went to buy one from the little hotel shop. They wanted $16 for a cheap wall plug that didn't even come with a cord.

Reviewed on Oct 29, 2026

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $2,637, price is now CA $1,860 per person
CA $1,860
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Richmond (RIC)
8.8/10 Excellent! (1,419 reviews)
Rooms are big, but not clean enough. Bathroom is not updated and looks deteriorated. Valet parking service is very slow. Location is good.

Reviewed on Oct 29, 2026

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was CA $1,100, price is now CA $777 per person
CA $777
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
8.4/10 Very good! (1,002 reviews)

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was CA $1,664, price is now CA $1,234 per person
CA $1,234
per person
Dec 29 - Jan 2
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,285 reviews)
Great restaurant and fantastic location

Reviewed on Oct 29, 2026

The Hotel at Arundel Preserve

The Hotel at Arundel Preserve

3.5 out of 5
Arundel Mills
Price was CA $986, price is now CA $766 per person
CA $766
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (2,009 reviews)

Ready to book your vacation to Chestnut Hill?

 

Choose your dates

Chestnut Hill Hotel Deals

Best Western La Plata Inn

Best Western La Plata Inn

2.5 out of 5
6900 Crain Highway La Plata MD
The price is CA $94 per night from Nov 16 to Nov 17
CA $94
CA $107 total
Nov 16 - Nov 17
includes taxes & fees
Best Western La Plata Inn
River Edge Inn

River Edge Inn

2.5 out of 5
30 Colonial Ave Colonial Beach VA
Fully refundableReserve now, pay when you stay
The price is CA $88 per night from Nov 29 to Nov 30
CA $88
CA $111 total
Nov 29 - Nov 30
includes taxes & fees
River Edge Inn
My Place Hotel - Dahlgren/King George, VA

My Place Hotel - Dahlgren/King George, VA

2.5 out of 5
4235 Market Center Drive King George VA
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Nov 24 to Nov 25
CA $138
CA $152 total
Nov 24 - Nov 25
includes taxes & fees
9.6/10 Exceptional! (828 reviews)
"The rooms were clean and comfortable. The bathroom had plenty of counter space and was well lit and had a vent fan. The staff was friendly and helpful. We were surprised to have a room with a kitchenette for such a good rate. We'll be back when in the area!"

Reviewed on Oct 27, 2026

My Place Hotel - Dahlgren/King George, VA
See all 263 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Chestnut Hill

Spooky Ghosts of Fredericksburg Self-Guided Walking Tour

Spooky Ghosts of Fredericksburg Self-Guided Walking Tour

CA $24
per traveller
Spooky Ghosts of Fredericksburg Self-Guided Walking Tour
Fredericksburg Ghost Tour Discover Our Haunted Streets

Fredericksburg Ghost Tour Discover Our Haunted Streets

CA $45
per adult
100% of travellers recommend
Fredericksburg Ghost Tour Discover Our Haunted Streets
See all activities in Chestnut Hill

Frequently asked questions

How much does a Chestnut Hill vacation package cost?
Offering excellent value package deals from CA $733 on Expedia, you'll be pleasantly surprised at how much a vacation to Chestnut Hill costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chestnut Hill?
You can generally find lower prices and greater availability in January, February and March. Browse our cheap Chestnut Hill vacation packages and you could land some great off-season discounts.
How many days is enough for Chestnut Hill?
With a well-organized itinerary, you can easily tick off the most popular Chestnut Hill attractions in a few days. But if you want to discover hidden spots or take day trips, think about booking your Chestnut Hill vacation for longer.
How to find the best Chestnut Hill package deals?
Bagging a cheap Chestnut Hill package deal is a breeze with Expedia. After 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 personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Chestnut Hill package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Chestnut Hill vacation as a package?
You can enjoy significant savings on your Chestnut Hill break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best flight and hotel 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 vacation package to Chestnut Hill?
Score incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Chestnut Hill getaway.
How to plan a trip to Chestnut Hill?

  1. Pick your dates: What you plan to do in Chestnut Hill and your favourite season will help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your accommodations will probably be the biggest expense during your trip to Chestnut Hill.
  3. Set the duration of your trip: Start by making a list of all the activities and sights you'd like to get to in Chestnut Hill. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose a Chestnut Hill 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.