Valley Street Holidays

Photo by Assya A

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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.
  • 50-inch flat-screen TV with cable channels
    Jul 13 - Jul 16

    The Docent's Collection at 178 Middle Street + Flight

    Downtown Portland
    3 nights
    2.0 star property
    10/10 - Exceptional (23 reviews)
    "Beautiful, clean, modern room with modern amenities. Had everything you could need in an apartment even, and was so close to old for, everything was walking distance Staff with beyond friendly, helpful, assisting, and courteous. If I could give 6/5 stars instead I would have"
    Reviewed May 29, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    Save 100% on your flight
    S$1,217
    S$919
    per traveller
    found 4 hours ago
    The Docent's Collection at 178 Middle Street
  • Restaurant
    Jul 13 - Jul 16

    Portland Harbor Hotel + Flight

    Downtown Portland
    3 nights
    4.0 star property
    9.4/10 - Exceptional (1,757 reviews)
    "Staff was extremely gracious and helpful. From the valet to the front desk to the restaurant."
    Reviewed May 30, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    Save 100% on your flight
    S$1,344
    S$1,029
    per traveller
    found 4 hours ago
    Portland Harbor Hotel
  • Premium bedding, individually decorated, individually furnished
    Jul 13 - Jul 16

    Blind Tiger Portland - Danforth Street. + Flight

    West End
    3 nights
    3.5 star property
    9.6/10 - Exceptional (184 reviews)
    "The only real issue was the distance from all of the attractions and restaurants. "
    Reviewed May 15, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    Save 100% on your flight
    S$2,308
    S$1,787
    per traveller
    found 4 hours ago
    Blind Tiger Portland - Danforth Street.
  • Children’s activities
    Jul 13 - Jul 16

    Inn By The Sea + Flight

    Cape Elizabeth
    3 nights
    4.0 star property
    9.6/10 - Exceptional (317 reviews)
    "Very nice place, very cclean and friendly."
    Reviewed May 30, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    Save 100% on your flight
    S$2,119
    S$1,659
    per traveller
    found 4 hours ago
    Inn By The Sea
  • Living area
    Jul 13 - Jul 16

    The Docent's Collection at 121 Middle Street + Flight

    Downtown Portland
    3 nights
    3.5 star property
    9.6/10 - Exceptional (326 reviews)
    "The property is great. The amenities are quality- nothing is cheap… kitchen is stocked & utensils are not flimsy- bedding is nice. Some good touches like under mount lighting in the bathroom that comes on as you walk in- the temperature is easy to keep constant (which is rare in units) it’s very walkable and the parking is easy ($60 per night). Lots of good. The unit itself is very nice. My only complaint is that the furniture is stained and filthy… one chair had caked food and hair (a good..."
    Reviewed May 27, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    S$1,223
    S$991
    per traveller
    found 4 hours ago
    The Docent's Collection at 121 Middle Street

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
3.5/5(2 area reviews)

A noteworthy feature of Downtown Portland is its captivating waterfront views. While you're in town, be sure to stop and check out Cross Insurance Arena and Merrill Auditorium.

Find hotels in Downtown Portland

Top hotels in Valley Street

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 S$170 per night from 1 Jun to 2 Jun
S$170
1 Jun - 2 Jun
includes taxes & fees
8.8/10 Excellent! (1,119 reviews)
"Close to the family when visiting. This time, my room was not cleaned on Saturday or Sunday. In the past, my room has gotten cleaned every day."

Reviewed on 25 May, 2026

Inn at St John Portland In-Town
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 S$359 per night from 7 Jun to 8 Jun
S$359
7 Jun - 8 Jun
includes taxes & fees
9.4/10 Exceptional! (1,663 reviews)
"Portland Regency Inn and Spa is an amazing place to stay. It is centrally located in the Old Port area of Portland. The staff and amenities were incredible. Next time we visit Portland we will definitely stay again."

Reviewed on 30 May, 2026

Portland Regency Hotel & Spa
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
The price is S$402 per night from 7 Jun to 8 Jun
S$402
7 Jun - 8 Jun
includes taxes & fees
9.4/10 Exceptional! (1,757 reviews)
"Staff was extremely gracious and helpful. From the valet to the front desk to the restaurant."

Reviewed on 30 May, 2026

Portland Harbor Hotel
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.

Frequently asked questions

How much does a Valley Street holiday 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 holiday 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 holiday 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 neighbourhood'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 holiday?
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 travelling 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 holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our holiday 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 holiday package?
Don't worry if you're rethinking your Valley Street holiday 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 realise 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.

Popular places to visit

Fitzpatrick Stadium

Catch an event at Fitzpatrick Stadium during your trip to Portland. Amble around the area's waterfront or attend a sporting event.

Fitzpatrick Stadium

Thompson's Point

Commune with nature and explore the great outdoors at Thompson's Point during your travels in Portland. Stroll along the seaside or attend a sporting event in the area.

Thompson's Point

Things to do

Harbor Lights and Sights Cruise

Harbor Lights and Sights Cruise

S$68
per adult
90% of travellers recommend
Harbor Lights and Sights Cruise
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

S$19
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.