Dedham Vacations from $293

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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.

The Latest Dedham vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Springfield West Inn

Best Western Springfield West Inn

2.5 out of 5
Price was $437, price is now $293 per person
$293
per person
Nov 7 - Nov 9
found 21 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
7.8/10 Good! (1,001 reviews)
My room was comfortable and clean

Reviewed on Aug 21, 2025

EVEN Hotels Manchester Airport by IHG

EVEN Hotels Manchester Airport by IHG

3.5 out of 5
South End
Save 100% on your flight
Price was $681, price is now $400 per person
$400
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.8/10 Excellent! (884 reviews)
Hotel is beautiful. Front desk staff not helpful and seemed put out to answer questions.

Reviewed on Aug 20, 2025

Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

3 out of 5
Plymouth Downtown Waterfront District
Save 100% on your flight
Price was $662, price is now $394 per person
$394
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.2/10 Very Good! (1,007 reviews)
Great location and super convenient to waterfront dining

Reviewed on Aug 24, 2025

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Save 100% on your flight
Price was $1,218, price is now $836 per person
$836
per person
Oct 17 - Oct 22
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Boston (BOS)
9.6/10 Exceptional! (162 reviews)
We’ve been to the Cape many times over the past 20 years. The Sesuit Harbor House was conveniently located off Route 6a, but it was very quiet; you couldn’t hear the traffic at all. Phil and his staff are very attentive and friendly; the continental breakfast in a basket every morning (with local treats) was perfect! We will come back and hopefully with more family members. It was 10/10!

Reviewed on Aug 25, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $2,614, price is now $1,835 per person
$1,835
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on Aug 20, 2025

Don't see what you're looking for?
See all available trips from Columbus to Dedham
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Discover the most popular places to visit in Dedham

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

Fenway Park

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

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

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 featuring landscape views, a skyscraper and flowers

Boston Common

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

$79
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

$70
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

$30
per traveler
Liberty, Freedom, and Revolution: American History Tours Bundle
See all activities in Dedham

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
$152 nightly
The price is $176 total per night from Sep 1 to Sep 2
$176 total
Sep 1 - Sep 2
Total with taxes and fees
9.6/10 Exceptional! (3,273 reviews)
"Our second stay at the Seaport Hotel and everything was amazing. We will continue to use this hotel for all of our Boston visits."

Reviewed on Aug 24, 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
$215 nightly
The price is $251 total per night from Sep 1 to Sep 2
$251 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (3,868 reviews)
"Great hotel, nice staff, cool area"

Reviewed on Aug 25, 2025

Omni Boston Hotel at the Seaport
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
$194 nightly
The price is $226 total per night from Sep 1 to Sep 2
$226 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (3,699 reviews)
"Get a room with the city view, it is amazing. Surprising, that they don’t offer gluten free options at their much advertised breakfast."

Reviewed on Aug 25, 2025

citizenM Boston North Station
See all 3,574 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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Frequently asked questions

How much does a Dedham vacation package cost?
You'll find cheap prices from $293 on Expedia for your Dedham break. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Dedham costs.
What are the cheapest months to go to Dedham?
December, January and February are the best times to search for cheap Dedham vacation packages. Choosing to travel in less busy months means you can typically find reduced prices on accommodations and flights.
How many days is enough for Dedham?
To get the most out of a Dedham vacation, we suggest staying for 2 days. Divide your time between visiting Dedham Historical Society, Wilson Mountain Reservation and other well-known attractions, in addition to experiencing neighborhoods like Newton Highlands and Jamaica Hills - Pond. If you've got some time to spare, add a day trip to your Dedham vacation itinerary.
Is it worth booking a vacation package to Dedham?
It's no wonder a Dedham vacation is on the to-do list of many travelers. Popular attractions like Legacy Place are just the start of things to see and do here.
How to find the best Dedham package deals?
Bagging a cheap Dedham package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most economical Dedham package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Dedham vacation as a package?
You can enjoy significant savings on your Dedham break by booking a personalized vacation package. Click on the "Package" heading, then select 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 score a better deal.
When to book a vacation package to Dedham?
If you're considering an impromptu Dedham adventure, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Dedham?

  1. Choose when to travel: Check your diary and get packing. Your favorite time of year and the type of activities available will also help you decide when to escape to Dedham.
  2. Figure out your budget: Ensure you have enough money to cover everything from food and transportation to activities and flights. Your hotel will probably be the biggest expense during your trip to Dedham.
  3. Explore Dedham using Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to Dedham. You can also save your favorite places, collaborate with friends and family and manage your plans in one place.
  4. Work out your trip length: Consider how much time you'd like to spend exploring Dedham. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  5. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customized Dedham vacation package.
  6. Add on excursions and experiences: Take a look at our dedicated travel guide to find some incredible things to do in Dedham. Book tickets or make reservations in advance to save time and avoid the hassle of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Dedham vacation packages?
Jet off on your perfect escape to Dedham with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait for your next payday — we've joined forces with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stick to your budget and snag great deals before they disappear.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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