Dedham Vacations from $433

Book a Hotel + Flight or Car together to unlock savings

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.
Boston Lodge and Suites

Boston Lodge and Suites

Dorchester
Save 100% on your flight
$433
per person
Oct 5 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

$1,408
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (6 reviews)
We were in Boston for the Mammoth March in Hingham and needed a base for some sight seeing in Boston for the week. We did not have a rental car but the parking garage was easily accessible and secure. We were able to get ubers very easily from the location. The Chelsea train station was only a 5 min walk away and the trains were reliable and efficient. The support staff replied to all our messages in the chat option quickly and were very helpful. The kitchen was well stocked and set up. The apartment was clean and all the linens and towels were freshly laundred. Would recommend this place without hesitation.

Reviewed on Jun 15, 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
$1,972
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
We weren't quite sure what to expect in a hotel in the heart of Boston but were extremely pleased with the experience and the room. The room/suite was a perfect size to relax in after a busy day seeing the sights of the city, and while our view was of the city and not the harbor, it was nonetheless wonderful. The room was appointed very tastefully and invited you to rest, The hotel and room had an air of quiet luxury which we did not expect. We very much enjoyed having breakfast by the dock/water and each time, the wait staff were so friendly and helpful. There is no question we will stay there again should our plans take us to Boston. Thanks helping to make our anniversary trip so great!

Reviewed on Aug 12, 2026

The Atlas Hotel

The Atlas Hotel

Allston
Save 100% on your flight
$1,447
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (254 reviews)
The hotel was clean and well maintained. Very innovative designed. The staff was constantly hospitable - opening every door when we enter. The only downside was the room next to us was very loud on our last night which kept us up most of the night - nothing to do with the hotel. I didn’t complain and am hoping for some compensation back.

Reviewed on Aug 10, 2026

Good Hotels Boston

Good Hotels Boston

South End
Save 100% on your flight
$842
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8/10 Very Good! (55 reviews)
Very nice people and had excellent help!

Reviewed on Aug 7, 2026

Don't see what you're looking for?
See all available trips from Chicago to Dedham
View all trips

Stay near popular Dedham attractions

Legacy Place

9.0/10 (203 reviews)
Legacy Place offers an upscale open-air shopping experience with over 70 retailers in a downtown setting. Browse luxury brands, enjoy chef-driven restaurants, or catch a film at the premium Showcase Cinema de Lux.
See properties

Historic Dedham Square

8.4/10 (55 reviews)
Stroll through Dedham Square's historic streets lined with preserved centuries-old buildings. Browse unique boutiques, savor local cuisine, or time your visit for the vibrant farmers market or holiday festivities.
See properties

The Fairbanks House

8.2/10 (34 reviews)
Built in 1637, the Fairbanks House is North America's oldest surviving timber-frame house. Step through its centuries-old doorway to discover original family artifacts and experience authentic colonial architecture.
See properties

Wilson Mountain Reservation

8.0/10 (27 reviews)
This tranquil 207-acre reservation offers Dedham's largest natural escape with well-marked woodland trails. Explore diverse terrain with rocky outcrops, streams, and seasonal foliage on the popular 1.7-mile loop.
See properties

Dedham Historical Society

7.8/10 (47 reviews)
This 1888 museum houses American treasures including the oldest dated chair in America and a Paul Revere bell. Explore Dedham's history through fine decorative arts and rare founding documents in the historic archives.
See properties

Motherbrook Arts and Community Center

You can spend an afternoon browsing the exhibits at Motherbrook Arts and Community Center in Dedham. Check out the shops and top-notch restaurants in this family-friendly area.
See properties

What to do in Dedham

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
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

$46
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

$46
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
See all activities in Dedham

Dedham Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$219 nightly
$254 total
Aug 30 - Aug 31
Total with taxes and fees
Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$151 nightly
$176 total
Aug 13 - Aug 14
Total with taxes and fees
9/10 Wonderful! (2,812 reviews)
"A"

Reviewed on Aug 12, 2026

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
$270 nightly
$315 total
Aug 30 - Aug 31
Total with taxes and fees
Omni Boston Hotel at the Seaport
See all 3,982 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.

Find the Best Dedham Vacation Packages

Dedham Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
24,700
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
New England Aquarium, Boston Museum of Fine Arts and Museum of Science

More vacations you might like

Frequently asked questions

How much does a Dedham vacation package cost?
You'll find cheap prices from $433 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

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