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.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $1,446, price is now CA $897 per person
CA $897
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,988, price is now CA $1,829 per person
CA $1,829
per person
Aug 29 - Sep 2
found 14 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Couldn’t ask for a better place to stay while in Boston.

Reviewed on Jul 13, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Price was CA $10,261, price is now CA $6,763 per person
CA $6,763
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
10/10 Exceptional! (9 reviews)
It was an amazing relaxing place. Very family friendly

Reviewed on Jul 12, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,397, price is now CA $939 per person
CA $939
per person
Aug 21 - Aug 24
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The staff here was so kind and thoughtful. The breakfast was amazing all 3 days and the beach was very quiet and great waterfront. The section we stayed has not been updated like some of the other units but was fine and comfortable. The general location was good and easily walkable to food and drink places. Overall, we enjoyed it and would stay here again for sure.

Reviewed on Jul 12, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,717, price is now CA $2,553 per person
CA $2,553
per person
Sep 30 - Oct 3
found 12 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

Ready to book your vacation to Dedham?

 

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Dedham Hotel Deals

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 $282 per night from Jul 26 to Jul 27
CA $282
CA $376 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (4,584 reviews)
"Great location very nice staff"

Reviewed on Jul 14, 2026

Seaport Hotel Boston
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
The price is CA $214 per night from Aug 9 to Aug 10
CA $214
CA $290 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (2,456 reviews)
"Staff was very helpful and friendly."

Reviewed on Jul 14, 2026

Hyatt Regency Boston/Cambridge
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Aug 2 to Aug 3
CA $225
CA $262 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,743 reviews)
"It was a nice place to stay in the lofts with a private entrance away from the activity and nice large bathroom in comfortably sized room with lots of practical storage space. The room also has good air quality control"

Reviewed on Jul 13, 2026

The Revolution Hotel
See all 3,978 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.
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Stay near popular Dedham attractions

Legacy Place

9.0/10 (203 reviews)
You can search for that perfect souvenir at Legacy Place during your trip to Dedham. Stroll along the riverfront or visit the churches in this vibrant area.
See properties

What to do in Dedham

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $73
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $119
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

CA $68
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
See all activities in Dedham

Frequently asked questions

How much does a Dedham vacation package cost?
You'll find cheap prices from CA $897 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.

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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.