Dedham Vacations from $1,247
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Your Dedham Vacation
Let our vacation packages to Dedham inspire your next great adventure. There's tons to love about this amazing city, starting with the neighborhood of Frankfort, which is great for culture and hiking. Your trip to Dedham wouldn't be complete without swinging by its major attractions, like Phillips Lake. Stop daydreaming and start traveling. Browse the multitude of options on Expedia today and put your Dedham vacation plans into gear!
The Latest Dedham Vacation Packages
- Hollywood Casino Bangor
Dec 26 - Dec 30Hollywood Casino Bangor + Flight
Bangor4 nights3.0 star property8.8/10 - Excellent (1,586 reviews)Roundtrip • Pittsburgh (PIT) - Bangor (BGR)PIT - BGR • 1 stop BGR - PIT • 1 stop$1,314$1,247found 1 day agoper traveler - The Primrose
Dec 26 - Dec 30The Primrose + Flight
Bar Harbor4 nights3.0 star property9.8/10 - Exceptional (997 reviews)"So adorable, breakfast was enjoyable, it was a nice walk to the downtown area although it’s not very well lit at night so FYI, you may want to bring a flashlight if you plan on being out after sunset. The beds were really comfortable, we enjoyed the extra plush robes and fancy local soap. The staff was all really nice – it was exactly the experience we were hoping for."Reviewed November 2, 2026Roundtrip • Pittsburgh (PIT) - Bangor (BGR)PIT - BGR • 1 stop BGR - PIT • 1 stop$1,388$1,308found 1 day agoper traveler - The Pathmaker Hotel
Dec 26 - Dec 30The Pathmaker Hotel + Flight
Bar Harbor4 nights2.0 star property9.8/10 - Exceptional (759 reviews)"We had a wonderful stay at The Pathmaker Hotel in Bar Harbor! The rooms are exceptionally spacious, comfortable, and inviting. The staff was incredibly friendly, welcoming, and always willing to help with anything we needed. Their hospitality made our stay even more enjoyable. We truly appreciated the excellent service and would definitely recommend The Pathmaker to anyone visiting Bar Harbor!"Reviewed November 8, 2026Roundtrip • Pittsburgh (PIT) - Bangor (BGR)PIT - BGR • 1 stop BGR - PIT • 1 stop$1,378$1,301found 1 day agoper traveler - The Inn on Mount Desert
Dec 26 - Dec 30The Inn on Mount Desert + Flight
Bar Harbor4 nights3.0 star property9.6/10 - Exceptional (1,003 reviews)"This is a beautiful place with a great location and wonderful breakfast. I would recommend it and would stay there again if I get the opportunity"Reviewed November 8, 2026Roundtrip • Pittsburgh (PIT) - Bangor (BGR)PIT - BGR • 1 stop BGR - PIT • 1 stop$1,386$1,310found 1 day agoper traveler - Hotel Ursa
Dec 26 - Dec 30Hotel Ursa + Flight
Orono4 nights4.0 star property9.6/10 - Exceptional (936 reviews)Roundtrip • Pittsburgh (PIT) - Bangor (BGR)PIT - BGR • 1 stop BGR - PIT • 1 stop$1,314$1,252found 1 day agoper traveler
Discover the most popular places to visit in Dedham
Dedham Hotel Deals
"Loved this little place! Beautiful property and view. The breakfast wasn’t anything special and continental style. With a restaurant on site it would have been nice to have a hot breakfast that was cooked. The staff was very accommodating and friendly. We asked for tea at night and the attendant brought us a tray with a tea pot, honey, cups with saucers…very thoughtful touch and appreciated. It is an older building, but still comfortable. Our room had a fireplace and towel warmer. I would...
"Updated, clean. Friendly staff. Location is great!"
"Clean and comfortable, very basic amenities. Good for a quick stay."
"Decent place to crash for the night. Good breakfast options. Helpful staff at the reception. Definitely worth the price!"
Frequently Asked Questions
How much does a Dedham vacation package cost?
You can grab a vacation package to this popular destination from $1,247 on Expedia. However, how much your vacation to Dedham costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Dedham?
October, November and December are the best times to search for cheap Dedham vacation packages. Choosing to travel in quieter months means you'll typically find reduced prices on flights and accommodations.
How many days is enough for Dedham?
With a well-planned schedule, you can easily tick off the main Dedham sights in a handful of days. But if you want to discover lesser-known spots or go on day trips, consider booking your Dedham vacation for longer.
How to find the best Dedham package deals?
Begin your search for a Dedham package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Dedham package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Dedham getaway off to a flying start.
Is it cheaper to book a Dedham vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels individually. Better still, you can personalize your Dedham getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Dedham?
If you're planning a spontaneous Dedham adventure, check out 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 flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Dedham vacation packages?
Set off on your ideal getaway to Dedham with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until your next paycheck — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stick to your budget and snap up travel deals while they last.