Valley Street Vacation Packages

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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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Top Holiday Package Deals in Valley Street

Price found within the past 48 hours. Click for updated prices.
HomeAwhile

HomeAwhile

4 out of 5
Price was CA $1,392, price is now CA $1,120 per person
CA $1,120
per person
Jun 19 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (12 reviews)
Clean and convenient. Loved the contactless entry.

Reviewed on Apr 8, 2026

The McKernan Inn

The McKernan Inn

3 out of 5
Price was CA $2,582, price is now CA $1,830 per person
CA $1,830
per person
Jun 19 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (93 reviews)
Beachfront old building labelled "Hospitality" has the best view I have ever seen for breakfast. Watch seals and fishing boats pass by while eating (included with room) continental breakfast freshly prepared just for you. Super private, clean, and well maintained. Feels historic, beach and walking path outside front door. Campus location, has campus security and feels very safe. Kids loved playing on the oceanfront. Makes good base for seeing Portland, but is located in South Portland. Check out the lighthouses!

Reviewed on Apr 7, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $3,433, price is now CA $2,612 per person
CA $2,612
per person
Jun 19 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,766 reviews)
Staff was amazingly nice and helpful! It will definitely be our favorite hotel in Maine! Thank you guys!

Reviewed on Apr 6, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $4,056, price is now CA $3,199 per person
CA $3,199
per person
Jun 19 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (178 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!

Reviewed on Mar 10, 2026

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
Price was CA $3,862, price is now CA $3,127 per person
CA $3,127
per person
Jun 19 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Nice room, staff was very nice and welcoming. Nice bar area

Reviewed on Mar 26, 2026

Where to stay in Valley Street

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

Downtown Portland

5 out of top 10 points of interest in this area

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

Valley Street Hotel Deals

Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
939 Congress St Portland ME
The price is CA $111 per night from Apr 9 to Apr 10
CA $111
CA $121 total
Apr 9 - Apr 10
includes taxes & fees
8.8/10 Excellent! (1,134 reviews)
Nice staff. I would stay again.

Reviewed on Apr 7, 2026

Inn at St John Portland In-Town
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
The price is CA $180 per night from Apr 22 to Apr 23
CA $180
CA $199 total
Apr 22 - Apr 23
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
I chose this hotel specifically because it was advertised as pet-friendly, as I was traveling with my well-trained dog. While the location was convenient and the room itself was comfortable, the experience was soured by the lack of transparency regarding the pet policy. When I booked, the additional ...

Reviewed on Apr 6, 2026

The Westin Portland Harborview
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
The price is CA $152 per night from Apr 22 to Apr 23
CA $152
CA $206 total
Apr 22 - Apr 23
includes taxes & fees
9.4/10 Exceptional! (1,186 reviews)
Clean, quiet, good stay.

Reviewed on Apr 6, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,458 properties in Valley Street
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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Valley Street vacation package cost?
Live it up in Valley Street from as little as CA $1,120. Choose from a great selection of hotels, flights and rental cars to suit your travel style. You can pick up even better deals when you add a few experiences or tours to your package.
How do I get a cheap travel package to Valley Street?
Simply by bundling. Hotels, rental cars and flights — combine whatever you need into a Valley Street vacation package to save a ton of cash. Score even more discounts when you add extras such as activities or tours to your booking. But that's not the only good part. You have the freedom to put together your trip your way. We offer more than 550 airlines and 1,000,000 hotel options in all corners of the globe, so that everyone has a chance to travel and live out those vacation dreams.
Where should I stay in Valley Street?
Most people who travel to Valley Street include University of Southern Maine and Portland Museum of Art on their must-see lists. Why not consider a hotel right near these main attractions?
What are the top hotels in Valley Street?
Reserve a room at Walk - In Modern Downtown One Bedroom. It's one of the neighborhood's most popular hotels. Another highly rated option in Valley Street is Stylish Walk - In Private One Bedroom Apt.
How far in advance should I book my Valley Street vacation?
While prices change frequently, we generally recommend booking your flight as soon as possible. Most international fares are available on Expedia up to 12 months in advance. If you're booking late, you might still get lucky. Discount prices to Valley Street occasionally appear in the weeks prior to departure.
What does an Expedia Valley Street travel package include?
It comes down to what you're looking for. If you're traveling alone, you might decide to bundle flights and hotels. Taking the whole family to Valley Street? A travel package that includes hotels, rental cars and flights might be a better fit. Expedia gives you the freedom to tailor your travel package.
What should I know before booking a Valley Street travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and enjoy terrific discounts. Hotels aren't your only option, however. We've got beachside condos, creek-side mountain cabins and just about everything in between!
Can I choose my airline with a Valley Street Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our vacation packages give you the flexibility to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Valley Street vacation package?
Don't worry if you're rethinking your Valley Street vacation package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We realize your circumstances can suddenly change, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Discover the most popular places to visit in Valley Street

State Theatre

State Theatre

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

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 $13
per traveller
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

CA $23
per traveller
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $21
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
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.