Dedham Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Your Dedham Vacation

There's no better way to escape than with one of our vacation packages to Dedham. The family-friendly attractions and rich history are just a couple of the compelling reasons to stay in this awesome city. If your trip to Dedham includes a little sightseeing, check out major attractions such as Franklin Park Zoo, Legacy Place and Blue Hills Ski Area. That dream Dedham vacation is just a few clicks away. Explore hotels, flights and more on Expedia for a trip that's tailored just for you.

Top Dedham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 1
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Beautiful Hotel and Great Location! Staff were so friendly and the waitress at The Dark Hour was so educational about the history of Boston! Love it!

Reviewed on Jul. 5, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful interior design

Reviewed on Jul. 3, 2025

Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

4 out of 5
Save 100% on your flight
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very Good! (1,475 reviews)
My stay at Hilton was okay overall. The staff were nice and welcoming, which I really appreciated. However, the location felt like it was in the middle of nowhere, making it a bit inconvenient. Another downside was the fridge in the lobby — it wasn’t working properly, so the yogurt and drinks weren’t cold. This made me hesitant to buy anything from there. Overall, it was an average stay with friendly staff, but the location and the issue with the lobby fridge took away from the experience.

Reviewed on Jul. 5, 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Beautiful hotel. Perfectly located

Reviewed on Jul. 4, 2025

Ready to book your vacation to Dedham?

 

Choose your dates

Dedham Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $314 per night from Jul 19 to Jul 20
CA $314
CA $422 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (3,630 reviews)
"We recently stayed at the Omni and overall had an enjoyable experience. The lobby is absolutely beautiful like spacious, clean, and very well maintained. It gives a great first impression, and the atmosphere feels upscale and welcoming. The staff were consistently friendly and helpful throughout ..."

Reviewed on Jul. 1, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Jul 6 to Jul 7
CA $223
CA $260 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (1,348 reviews)
"The location was great for where I wanted to be. Close to everything and easy to walk everywhere"

Reviewed on Jul. 3, 2025

citizenM Boston Back Bay
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is CA $280 per night from Jul 6 to Jul 7
CA $280
CA $326 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (5,274 reviews)
"Great location, very helpful and friendly staff. Ver nice restaurant and bar on site."

Reviewed on Jul. 4, 2025

Harborside Inn Of Boston
See all 3,538 properties in Dedham
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

Discover the most popular places to visit in Dedham

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(305 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

4.5/5(279 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common which includes flowers, a garden and landscape views

Boston Common

4.5/5(518 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

What to do in Dedham

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $75
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Dedham

Frequently asked questions

How much does a Dedham vacation package cost?
You'll find cheap prices from CA $969 on Expedia for your Dedham getaway. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Dedham costs.
What are the cheapest months to go to Dedham?
You're likely to find lower prices and greater availability in December, January and February. Explore our cheap Dedham vacation packages and you could get some great off-season deals.
How many days is enough for Dedham?
To get the most out of your Dedham vacation, we suggest booking for 2 days. Divide your time between discovering Samuel Adams Brewery, Blue Hills Ski Area and other key sights, as well as exploring neighbourhoods like Jamaica Plain and Jamaica Hills - Pond. If you've got some spare time, add a day trip to your Dedham vacation itinerary.
Is it worth booking a vacation package to Dedham?
Dedham offers everything you need for an amazing getaway. Get your Dedham vacation off to a flying start by visiting popular attractions like Kings Bowling.
How to find the best Dedham package deals?
Finding a cheap Dedham package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Dedham package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Dedham vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights individually. Better still, you can customize your Dedham trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Dedham?
If you're planning an impromptu Dedham adventure, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Dedham?

  1. Choose your travel dates: What you plan to do in Dedham and your preferred season will help you decide when to go.
  2. Plan your budget wisely: As well as the price of your accommodations, you'll need to factor in other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that could arise during your trip to Dedham.
  3. Decide how long to go for: Now that you're up to speed on Dedham, you can work out the ideal length of your break. Pull together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodations: After you've settled on your trip dates and duration, lock in the ideal Dedham vacation package for you.

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