Dedham Vacations from $707

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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.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was $1,133, price is now $707 per person
$707
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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
Save 100% on your flight
Price was $1,532, price is now $893 per person
$893
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
A beautiful Hotel w an excellent staff that provides superior service and helps to make our stay memorable. We will be back again.

Reviewed on Jul 6, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,563, price is now $1,566 per person
$1,566
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (720 reviews)
This is the real deal. Value AND LUXURY. Quality. And a staff that takes ownership in your vacations experience. Ownership creates an experience that is guest focused. I've worked in hotels and hospitality for over thirty years. And post Covid. It's not the same industry. What they've created makes me miss what I used to do. BRAVO guys. If you're thinking of it, just do it. It's worth it. More than you can imagine.

Reviewed on Jul 6, 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
Save 100% on your flight
Price was $5,601, price is now $3,666 per person
$3,666
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
10/10 Exceptional! (9 reviews)
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler

Reviewed on Oct 8, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,369, price is now $899 per person
$899
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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

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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

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
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

$45
per adult
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

$47
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
See all activities in Dedham

Dedham Hotel Deals

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
$168 nightly
The price is $195 total per night from Jul 26 to Jul 27
$195 total
Jul 26 - Jul 27
Total with taxes and fees
9/10 Wonderful! (2,419 reviews)
"The staff at the Hyatt in Cambridge was outstanding! Everyone was friendly, cheerful, and efficient, and they truly went above and beyond to make our stay special. They were happy to accommodate additional requests for our room and provided excellent recommendations for local entertainment and travel. ..."

Reviewed on Jul 7, 2026

Hyatt Regency Boston/Cambridge
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
$219 nightly
The price is $254 total per night from Jul 26 to Jul 27
$254 total
Jul 26 - Jul 27
Total with taxes and fees
9.6/10 Exceptional! (4,532 reviews)
"Was very near to harbour and other amenities . The room was very clean and had everything you could require for a good stay . Ate here on one evening and the food was good and a 15 dollar discount per person, made it even better value . Was not the best location for public transport as seemed to ..."

Reviewed on Jul 6, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $180 total per night from Aug 2 to Aug 3
$180 total
Aug 2 - Aug 3
Total with taxes and fees
9/10 Wonderful! (2,718 reviews)
"We had another wonderful stay at The Revolution Hotel. Its a lovely hotel, very clean and beautiful! In a perfect area that is centrally located. The shared bathrooms are NOT shared bathrooms. “Shared” sounds very intimidating, but they are actually individual bathroom suites. So you walk into the ..."

Reviewed on Jul 6, 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.

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

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Frequently asked questions

How much does a Dedham vacation package cost?
You'll find cheap prices from $707 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.