Valley Street Vacations from $398

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Your Valley Street Vacation

Make planning your travels hassle-free by booking a vacation package to Valley Street. We'll look after all the details, so you can concentrate on savoring everything this neighborhood can offer. Your trip to Valley Street wouldn't be complete without stopping by major attractions nearby such as Portland Museum of Art, University of Southern Maine and Victoria Mansion. Expedia is here to put your travel plans into action. Book your perfect Valley Street vacation today.

The Latest Valley Street Vacation Packages

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

84 Main

$398
per person
Nov 22 - Nov 24
found 2 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
9.8/10 Exceptional! (58 reviews)
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.

Reviewed on Jul 17, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

Downtown Portland
$1,512
per person
Dec 26 - Jan 1
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (400 reviews)
Amazing location and lots of space in Portland Maine. We loved it!!

Reviewed on Oct 14, 2026

The Meadowmere Resort

The Meadowmere Resort

$658
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
8.6/10 Excellent! (1,008 reviews)
Great mid-price range option! Still walking distance to most things you’ll want to do in ogunquit and they let you check in early just to park even if your room isn’t ready yet, which is valuable in of itself. The outdoor horrible was very spacious and the up keep of the entire property was very nice. Free continental breakfast too

Reviewed on Oct 11, 2026

Cliff House Maine

Cliff House Maine

Bald Head
$1,590
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

West End
$1,575
per person
Dec 26 - Jan 1
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (193 reviews)

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
A tree-lined pathway leading to a brick building with a sign reading "Mercy Hospital Service Entrance".

Downtown Portland

5 out of top 10 points of interest in this area

Known for its culinary delights, inspiring art and live music, the heart of Maine’s largest city is an exciting location.

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A marina with boats docked, a wooden pier, and a red brick building with balconies.

Old Port

Cobblestone streets, 19th-century brick buildings, and fishing piers define this district, offering boutiques, restaurants, and bars. Explore Post Office Park, Tommy's Park with its large mural, and stroll the Eastern Promenade Trail to East End Beach.

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A lighthouse on a rocky shore with a sailboat in the distance.

West End

Distinguished by its well-preserved Victorian architecture, this downtown Portland neighborhood boasts the scenic Western Promenade park, offering views of the White Mountains, and several historic structures, such as the Gothic House and Morrill Mansion.

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A large, cream-colored building with white columns and a white picket fence in front.

Portland Arts District

The ample dining options and captivating waterfront views are top of the list for many visitors to Portland Arts District. A stop by Cross Insurance Arena or Portland Museum of Art might round out your trip.

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An aerial view of a coastal town with houses, a parking lot, and a rocky shoreline.

West Bayside

If you're looking for some top things to see and do in West Bayside and surrounding area, you can visit Merrill Auditorium and Cross Insurance Arena.

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Valley Street Hotel Deals

Inn at St John Portland In-Town

Inn at St John Portland In-Town

939 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$89 nightly
$97 total
Oct 29 - Oct 30
Total with taxes and fees
8.6/10 Excellent! (1,169 reviews)
"We love to stay at historic places when we travel, and we were not disappointed with this one! So cute and cozy!"

Reviewed on Oct 15, 2026

Inn at St John Portland In-Town
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME
Fully refundable
$83 nightly
$92 total
Nov 1 - Nov 2
Total with taxes and fees
Clarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

157 High St Portland ME
Fully refundableReserve now, pay when you stay
$127 nightly
$141 total
Nov 11 - Nov 12
Total with taxes and fees
The Westin Portland Harborview
See all 2,499 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
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Beach Vacations
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Kid Friendly Vacations
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Golf Vacations
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Luxury Vacations
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Romantic Vacations
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Ski Vacations
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LGBTQ Friendly Vacations
Adventure Vacations
Adventure Vacations
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Where to go when
Where to go when
Honeymoon Vacations
Honeymoon Vacations
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Mountain Vacations
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Fishing Vacations
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Adults Only Vacations
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Waterpark Vacations
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Yoga Vacations
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Cheap Vacations
Solo Vacations
Solo Vacations

Stay near popular Valley Street attractions

Hadlock Field

9.8/10 (6 reviews)
Catch an event at Hadlock Field during your trip to Portland. Amble around the area's waterfront or attend a sporting event.
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Portland Exposition Building

8.0/10 (3 reviews)
Learn about the events happening at Portland Exposition Building during your trip to Portland. Experience the area's entertainment choices and acclaimed theater scene.
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Fitzpatrick Stadium

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

Catch an event at Home of the Maine Celtics during your trip to Portland.
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Things to do

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

$77
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland: Casco Bay Morning Lighthouse Cruise

Portland: Casco Bay Morning Lighthouse Cruise

$59
per adult
80% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
Sunset Lighthouse Cruise Along Casco Bay

Sunset Lighthouse Cruise Along Casco Bay

$69
per adult
Sunset Lighthouse Cruise Along Casco Bay
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.