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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Price was CA $701, price is now CA $493 per person
CA $493
per person
Nov 13 - Nov 16
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Washington (WAS)
8/10 Very Good! (1,007 reviews)
The room was excellent. It was big and roomy and well furnished. The beds were very comfortable. The shower was nice. The staff was wonderful. They were happy to help. The hotel is easily accessed by bus.

Reviewed on Aug. 26, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Price was CA $1,114, price is now CA $736 per person
CA $736
per person
Nov 13 - Nov 16
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Washington (WAS)
9.8/10 Exceptional! (39 reviews)
The staff is extremely friend, adn the foods in the restaurant are wonderful

Reviewed on Aug. 26, 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Price was CA $956, price is now CA $640 per person
CA $640
per person
Nov 13 - Nov 16
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Washington (WAS)
8.6/10 Excellent! (1,006 reviews)
Good location, friendly staff, great breakfast, clean and quiet rooms, best sleep in a week

Reviewed on Aug. 12, 2025

The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Price was CA $1,032, price is now CA $693 per person
CA $693
per person
Oct 1 - Oct 5
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Washington (WAS)
8.2/10 Very Good! (1,005 reviews)
Front desk was super helpful and responsive

Reviewed on Aug. 23, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was CA $1,040, price is now CA $724 per person
CA $724
per person
Oct 8 - Oct 11
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
Beautiful place! Amazing staff!

Reviewed on Aug. 21, 2025

Ready to book your vacation to Chestnut Hill?

 

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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 $150 per night from Aug 27 to Aug 28
CA $150
CA $180 total
Aug 27 - Aug 28
includes taxes & fees
8.2/10 Very Good! (350 reviews)
"Was a great stay"

Reviewed on Aug. 15, 2025

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 $116 per night from Sep 7 to Sep 8
CA $116
CA $127 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (573 reviews)
"The property was well cared for, nice employees, comfortable room. All great , but no breakfast. I will not stay there again."

Reviewed on Aug. 25, 2025

My Place Hotel - Dahlgren/King George, VA
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 $100 per night from Sep 1 to Sep 2
CA $100
CA $113 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very Good! (1,006 reviews)
"The staff was very helpful."

Reviewed on Aug. 21, 2025

Best Western La Plata Inn
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.
All Inclusive Vacations
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Frequently asked questions

How much does a Chestnut Hill vacation package cost?
Offering excellent value package deals from CA $493 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.