Chestnut Hill Vacation Packages

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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.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $845, price is now CA $612 per person
CA $612
per person
Sep 4 - Sep 7
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,373 reviews)
The staff was exceptional, great hospitality! The room had several minor issues, shower door didn’t stay closed, vanity was missing a leg, power bank on one side of the bed didn’t work, a random ballon was on the ceiling(granted we didn’t notice it one of the staff did while trying to get the power bank to work) bar and restaurant was out of multiple items.

Reviewed on Jul 13, 2026

The Georgetown House

The Georgetown House

3 out of 5
Northwest
Price was CA $1,490, price is now CA $1,101 per person
CA $1,101
per person
Sep 14 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (640 reviews)
Close to the wharf, eat breakfast at Farmers on the water. Fresh and tasty, under $20. Ate Italian food for dinner at Canala, restaurant next door to Inn.

Reviewed on Jul 8, 2026

Hyatt Place Washington DC/US Capitol

Hyatt Place Washington DC/US Capitol

3 out of 5
Northeast
Price was CA $1,762, price is now CA $1,334 per person
CA $1,334
per person
Sep 14 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
7.4/10 Good! (1,205 reviews)
Our shower had hair in it before we got in. The sink wouldn’t stay up for water to go down. The pool was cloudy and there is only one shower door so the bathroom floor and toilet would get water everywhere. The breakfast was ok. And one side of the hotel seemed a little sketchy and unsafe and you need your room key to get into the hotel and ride the elevator. Wouldn’t recommend if you were traveling alone.

Reviewed on Jul 13, 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was CA $1,030, price is now CA $789 per person
CA $789
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
8.2/10 Very good! (1,005 reviews)
Overall it was a good stay the room was clean.The staff was good in the beginning but at checkout the women working the front desk was rude and acted as if she didn’t want to be ask questions about the shuttles. And there was a problem with the printer I assume because I never received my receipt and she said she would email it .

Reviewed on Jul 13, 2026

Hotel Madera

Hotel Madera

4 out of 5
Downtown Washington D.C.
Price was CA $1,042, price is now CA $809 per person
CA $809
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
9.2/10 Wonderful! (1,007 reviews)
Great location and nice spacious room - A/C was out third night with no notification from staff and the water station did not work on our floor.. unacceptable in the extreme heat. Housekeeping did not do a great job.

Reviewed on Jul 9, 2026

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Chestnut Hill Hotel Deals

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 $134 per night from Jul 16 to Jul 17
CA $134
CA $163 total
Jul 16 - Jul 17
includes taxes & fees
8.2/10 Very good! (466 reviews)
"Very good experience.!!!!"

Reviewed on Jul 9, 2026

River Edge Inn
Best Western La Plata Inn

Best Western La Plata Inn

2.5 out of 5
6900 Crain Highway La Plata MD
Fully refundableReserve now, pay when you stay
The price is CA $96 per night from Jul 19 to Jul 20
CA $96
CA $109 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very good! (1,014 reviews)
"Great place"

Reviewed on Jul 13, 2026

Best Western La Plata 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 $129 per night from Aug 9 to Aug 10
CA $129
CA $142 total
Aug 9 - Aug 10
includes taxes & fees
9.6/10 Exceptional! (782 reviews)
"The rooms are very clean, and the property is within walking distance of grocery stores, gas stations, and shopping centers."

Reviewed on Jul 10, 2026

My Place Hotel - Dahlgren/King George, VA
See all 256 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
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What to do in Chestnut Hill

Fredericksburg Walking Tour

Fredericksburg Walking Tour

CA $41
per adult
Fredericksburg Walking Tour
Fredericksburg Ghost Tour Discover Our Haunted Streets

Fredericksburg Ghost Tour Discover Our Haunted Streets

CA $41
per adult
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 $612 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.

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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.