East Bayside Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Price found within the past 48 hours. Click for updated prices.
  • Indoor spa tub
    Jul 7 - Jul 10

    The Meadowmere Resort + Flight

    Ogunquit
    3 nights
    2.5 star property
    8.6/10 - Excellent (1,001 reviews)
    "Clean room , friendly Staff , Breakfast was great !! "
    Reviewed May 13, 2026
    Roundtrip • Detroit (DTW) - Boston (BOS)
    DTW - BOS • 1 stop BOS - DTW • 1 stop
    CA $1,211
    CA $904
    per traveller
    found 8 hours ago
    The Meadowmere Resort
  • Lobby sitting area
    Jul 23 - Jul 27

    Ogunquit River Inn & Suites + Flight

    Ogunquit
    4 nights
    3.0 star property
    9.0/10 - Wonderful (1,003 reviews)
    "Yes"
    Reviewed May 11, 2026
    Roundtrip • Montreal (YUL) - Boston (BOS)
    YUL - BOS • Nonstop BOS - YUL • Nonstop
    CA $2,039
    CA $1,393
    per traveller
    found 11 hours ago
    Ogunquit River Inn & Suites
  • Indoor pool, seasonal outdoor pool, open 8 AM to 8:00 PM, sun loungers
    Jul 7 - Jul 10

    Cliff House Maine + Flight

    Bald Head
    3 nights
    4.5 star property
    9.4/10 - Exceptional (1,005 reviews)
    "Amazing stay!"
    Reviewed May 18, 2026
    Roundtrip • Detroit (DTW) - Boston (BOS)
    DTW - BOS • 1 stop BOS - DTW • 1 stop
    CA $2,816
    CA $1,977
    per traveller
    found 8 hours ago
    Cliff House Maine
  • Exterior
    Jul 7 - Jul 10

    Cambria Hotel Portland Downtown-Old Port + Flight

    Downtown Portland
    3 nights
    3.0 star property
    9.4/10 - Exceptional (1,223 reviews)
    "Rooms are fantastic! Great view! Lots of nice small amenities."
    Reviewed May 16, 2026
    Roundtrip • Detroit (DTW) - Boston (BOS)
    DTW - BOS • 1 stop BOS - DTW • 1 stop
    CA $1,268
    CA $924
    per traveller
    found 8 hours ago
    Cambria Hotel Portland Downtown-Old Port
  • Deluxe Suite, 1 King Bed | Private kitchen
    Aug 8 - Aug 12

    The Weldon Hotel + Flight

    Downtown Portland
    4 nights
    4.5 star property
    9.8/10 - Exceptional (101 reviews)
    "Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again"
    Reviewed April 23, 2026
    Roundtrip • Detroit (DTW) - Portland (PWM)
    DTW - PWM • 1 stop PWM - DTW • 1 stop
    CA $2,848
    CA $2,203
    per traveller
    found 1 day ago
    The Weldon Hotel

Where to stay in East Bayside

Find the best East Bayside areas and neighborhoods for the activities you enjoy most. Learn more about East Bayside
Downtown Portland

Downtown Portland

4 out of top 10 points of interest in this area
4.5/5(11 area reviews)

Downtown Portland is known for its captivating waterfront views, and with sights like Cross Insurance Arena and Merrill Auditorium, you won't get bored spending a day wandering around this part of Portland.

Find hotels in Downtown Portland

East Bayside Hotel Deals

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $255 per night from May 25 to May 26
CA $255
CA $335 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (1,777 reviews)
"Location is fantastic and staff was friendly. The room and common areas were acceptably clean. The room was pretty basic and felt a little cramped but I could have booked a suite and didn’t. Some of the maintenance could have been done better, which would have been more fitting for a well restored ..."

Reviewed on May 19, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from May 26 to May 27
CA $221
CA $244 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,660 reviews)
"We had breakfast both days of our weekend at the lovely first floor dining room. The tables were beautifully set and the food delicious. Both Patrick and John were standouts on the dining staff."

Reviewed on May 18, 2026

Portland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $229 per night from May 26 to May 27
CA $229
CA $290 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,223 reviews)
"Rooms are fantastic! Great view! Lots of nice small amenities."

Reviewed on May 16, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,411 properties in East Bayside
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.
All Inclusive Vacations
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Frequently asked questions

How much does an East Bayside vacation package cost?
Say yes to new adventures with our East Bayside vacation packages, which start from only . Handpick the flights and hotels that suit your style. Then, add on a few sightseeing tours for a memorable getaway.
How do I get a cheap travel package to East Bayside?
Combine your bookings with Expedia to save big bucks on your next exciting adventure. With more than 550 air carriers and 1,000,000 hotels across the world, your East Bayside vacation package can be customized exactly to suit your travel style. With all those extra dollars, why not include a few interesting tours and activities? It's an easy way to unlock even more savings. Your dream getaway to East Bayside is much closer than you thought!
Where should I stay in East Bayside?
A journey to East Bayside isn't over until you've seen University of Southern Maine and Portland Museum of Art. Stay at a hotel nearby for quick access to these famous attractions.
What are the top hotels in East Bayside?
If it's your first visit to East Bayside, lock in a room at Portland Peninsula - Spacious Walkable East End Spot or Spacious And Contemporary Condo In The Heart Of Portland. Both hotels offer friendly service and are favorites among many travelers.
How far in advance should I book my East Bayside vacation?
It all depends on the airline, but you can usually compare international airfares on Expedia up to a year in advance. While it's generally a good idea to book ahead of time, lucky customers will sometimes nab a cheaper flight just weeks prior to the date of departure.
What does an Expedia East Bayside travel package include?
It comes down to what you want. If you're traveling solo, you might decide to combine flights and hotels. Bringing the whole crew to East Bayside? A travel package including rental cars, flights and hotels might be a better fit. Expedia gives you the flexibility and freedom to build your own travel package.
What should I know before booking an East Bayside travel package?
Tailor deals to suit your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your escape. You'll save loads just by combining your bookings. Whether you're embarking on an adventure in the snow or sipping cocktails on a beach, your dream vacation is just a few clicks away.
Can I choose my airline with an East Bayside Expedia vacation package?
Yes, the choice is all yours. We have access to over 550 partner airlines worldwide, so you can design your East Bayside adventure according to your needs and budget.
If I'm not able to travel, can I cancel my East Bayside vacation package?
Don't worry if you're rethinking your East Bayside vacation package — you can cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We realize your circumstances can change suddenly, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.

Discover the most popular places to visit in East Bayside

State Theatre

State Theatre

4.5/5(5 reviews)

The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

State Theatre
Portland Museum of Art

Portland Museum of Art

5/5(5 reviews)

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

Portland Museum of Art
East End Beach

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach

Things to do

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

CA $14
per traveller
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
See all activities in Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.