Dedham Vacation Packages

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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.
Staybridge Suites Boston Logan Airport - Revere by IHG

Staybridge Suites Boston Logan Airport - Revere by IHG

3 out of 5
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (536 reviews)
Staff were amazing! Room was great, didn’t care for the tv placement but other than that it was clean and quiet and plenty of places near to eat and shop. Also love the free shuttle to and from the airport!

Reviewed on Jul. 9, 2025

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 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 12 - Aug 16
found 16 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Great hotel, friendly staff, great gym and spa.

Reviewed on Jul. 7, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 12 - Aug 16
found 16 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
First class hotel with incredible staff and food onsite. Walk to anywhere downtown and the north end for great Italian food

Reviewed on Jul. 8, 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 17
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (3,026 reviews)
Place was beautiful well kept and very clean

Reviewed on Jul. 8, 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 $289 per night from Aug 10 to Aug 11
CA $289
CA $392 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (3,651 reviews)
"We just had a wonderful stay at the Omni seaport ! It was July 4th weekend so it was. Busy but still the hotel was very attentive and organized . From valet to front desk , to the pool staff everyone was friendly and helpful and also had in room dining for breakfast from kestra ans it was amazing ..."

Reviewed on Jul. 8, 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 $252 per night from Jul 13 to Jul 14
CA $252
CA $293 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (1,394 reviews)
"Check in was self serving and simple. Big fan of the room controls through the app and iPad in the room. Blackout curtains and complementary refillable water bottles are a fantastic incentive."

Reviewed on Jul. 8, 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 $282 per night from Jul 13 to Jul 14
CA $282
CA $328 total
Jul 13 - Jul 14
includes taxes & fees
9/10 Wonderful! (5,289 reviews)
"The room was very roomy for a Boston Hotel! Beds were comfortable and the service was excellent. We loved the location and convenience to all areas of Boston. We will stay here again!"

Reviewed on Jul. 8, 2025

Harborside Inn Of Boston
See all 3,539 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 $685 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.