Dedham Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,221, price is now CA $760 per person
CA $760
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,836, price is now CA $1,681 per person
CA $1,681
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on Aug. 11, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,019, price is now CA $1,280 per person
CA $1,280
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
The room was 5 star and it’s in an ideal location in central Boston. View of Boston harbor is amazing, of course. Restaurant on the harbor was good and the service there was great.

Reviewed on Aug. 19, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Price was CA $2,226, price is now CA $1,425 per person
CA $1,425
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on Jul. 17, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,143, price is now CA $1,405 per person
CA $1,405
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
The beds are the main thing that keep me coming black, so comfortable, especially after a long day of walking around Boston. I will say we were disappointed that the inside of our coffee machine was very dirty.. something i think shouldn't be missed when cleaning since we love a good morning coffee in the room , but had to settle for going to a coffee shop. We tried ordering room service , but after waiting over 1hr we ended up calling to cancel it. For the amount of money we paid , i think they could step their game up when it comes to service and details.

Reviewed on Aug. 16, 2025

Ready to book your vacation to Dedham?

 

Choose your dates

Dedham Hotel Deals

citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $241 per night from Aug 24 to Aug 25
CA $241
CA $281 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (3,667 reviews)
"For a small room it was very well laid out. Loved the decor and the staff were very friendly and helpful. We did not have the breakfast but nice to have that option."

Reviewed on Aug. 18, 2025

citizenM Boston North Station
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Sep 1 to Sep 2
CA $225
CA $268 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,255 reviews)
"Superb location. Excellent value."

Reviewed on Aug. 19, 2025

Seaport Hotel Boston
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 $321 per night from Sep 5 to Sep 6
CA $321
CA $430 total
Sep 5 - Sep 6
includes taxes & fees
9/10 Wonderful! (3,854 reviews)
"We did not realize that you needed reservations for pool chairs. They do open up after 30 minutes if there are chairs available. Pool staff were excellent but other guests can be rude. The only unpleasant part of our stay."

Reviewed on Aug. 19, 2025

Omni Boston Hotel at the Seaport
See all 3,567 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 $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $97
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 $760 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.