Valley Street Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Deluxe Room, 2 Queen Beds, Non Smoking
    Jun 27 - Jul 3

    Saco Bay Hotel + Flight

    Saco
    6 nights
    2.5 star property
    7.6/10 - Good (1,059 reviews)
    "."
    Reviewed May 24, 2026
    Roundtrip • Toronto (YYZ) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $1,914
    CA $1,433
    per traveller
    found 1 day ago
    Saco Bay Hotel
  • Restaurant
    Jun 27 - Jul 3

    Portland Harbor Hotel + Flight

    Downtown Portland
    6 nights
    4.0 star property
    9.4/10 - Exceptional (1,767 reviews)
    "Location Location. Valet parking could be more reasonable!!"
    Reviewed May 24, 2026
    Roundtrip • Toronto (YYZ) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $2,990
    CA $2,299
    per traveller
    found 1 day ago
    Portland Harbor Hotel
  • Studio, 1 Queen Bed | Private kitchen
    Jun 27 - Jul 3

    The Docent's Collection at 121 Middle Street + Flight

    Downtown Portland
    6 nights
    3.5 star property
    9.6/10 - Exceptional (324 reviews)
    "Très bien, mais soyez préparés à utiliser une application sur votre téléphone pour entrer et sortir"
    Reviewed May 25, 2026
    Roundtrip • Toronto (YYZ) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $3,316
    CA $2,592
    per traveller
    found 1 day ago
    The Docent's Collection at 121 Middle Street
  • Deluxe Suite, 1 King Bed | Private kitchen
    Aug 20 - Aug 23

    The Weldon Hotel + Flight

    Downtown Portland
    3 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 • Toronto (YYZ) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $2,422
    CA $1,927
    per traveller
    found 7 hours ago
    The Weldon Hotel
  • View from property
    Jun 27 - Jul 3

    Chebeague Island Inn + Flight

    Chebeague Island
    6 nights
    4.0 star property
    8.8/10 - Excellent (77 reviews)
    "Charming and easy access to the Golf Course "
    Reviewed September 21, 2025
    Roundtrip • Toronto (YYZ) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $2,375
    CA $1,975
    per traveller
    found 1 day ago
    Chebeague Island Inn

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

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

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
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from May 26 to May 27
CA $187
CA $204 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (1,131 reviews)
"Absolutely enjoyed our stay! The parking was excellent and breakfast was perfect with excellent coffee. We absolutely loved the old world charm of the hotel. Loved the many stairs to our room, it was a lot of fun."

Reviewed on May 24, 2026

Inn at St John Portland In-Town
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 $295 per night from May 31 to Jun 1
CA $295
CA $380 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,767 reviews)
"Location Location. Valet parking could be more reasonable!!"

Reviewed on May 24, 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 $247 per night from May 27 to May 28
CA $247
CA $274 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (1,648 reviews)
"Exactly what we wanted. Quiet, romantic, great location."

Reviewed on May 24, 2026

Portland Regency Hotel & Spa
See all 2,481 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 . 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

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

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.