Stroudwater Vacations from $352

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Your Stroudwater Vacation

Take the stress out of organizing your next break by booking a Stroudwater vacation package. Take in the sounds and sights of this wonderful neighborhood and experience all it has to offer. Want to head out and see the sights during your trip to Stroudwater? Pencil in a visit to nearby attractions like University of Southern Maine, Maine Mall and Thompsons Point. Stop daydreaming and start doing. When you're ready to lock in your dream vacation to Stroudwater, Expedia will help get you there.

The Latest Stroudwater Vacation Packages

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

84 Main

4 out of 5
Save 100% on your flight
Price was $547, price is now $352 per person
$352
per person
Mar 19 - Mar 24
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.

Reviewed on Dec 29, 2025

InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Save 100% on your flight
Price was $484, price is now $372 per person
$372
per person
Mar 19 - Mar 24
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (356 reviews)
Wonderful staff, quick easy check in & out, gorgeous location and great in-room jacuzzi tub!

Reviewed on Jan 23, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was $948, price is now $780 per person
$780
per person
Apr 17 - Apr 19
found 14 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Phenomenal service and food with stunning east coast views. A favorite for sure.

Reviewed on Jan 23, 2026

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $469, price is now $388 per person
$388
per person
Apr 17 - Apr 19
found 14 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Room was very clean, neat vibe, tons of space! Made coming back from

Reviewed on Jan 23, 2026

Where to stay in Stroudwater

Find the best Stroudwater areas and neighborhoods for the activities you enjoy most. Learn more about Stroudwater
State Street Church

Downtown Portland

4 out of top 10 points of interest in this area
4.5/5(326 area reviews)

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

Find hotels in Downtown Portland

Stroudwater Hotel Deals

Long Creek Hotel by IHG

Long Creek Hotel by IHG

2.5 out of 5
171 Philbrook Ave South Portland ME
Fully refundable
$78 nightly
The price is $85 total per night from Feb 4 to Feb 5
$85 total
Feb 4 - Feb 5
Total with taxes and fees
7.4/10 Good! (1,006 reviews)
Clean room, comfortable beds, pet friendly, and very professional and personable staff. Extended my stay for another night

Reviewed on Jan 30, 2026

Long Creek Hotel by IHG
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$141 nightly
The price is $156 total per night from Feb 9 to Feb 10
$156 total
Feb 9 - Feb 10
Total with taxes and fees
9.2/10 Wonderful! (1,745 reviews)
Room very clean. All staff professional and courteous

Reviewed on Jan 30, 2026

Portland Harbor Hotel
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Feb 7 to Feb 8
$92 total
Feb 7 - Feb 8
Total with taxes and fees
8/10 Very Good! (1,336 reviews)
Very helpful and very clean room

Reviewed on Jan 21, 2026

Clarion Hotel Portland Airport ME
See all 2,384 properties in Stroudwater
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

Discover the most popular places to visit in Stroudwater

State Theatre showing street scenes as well as an individual femail

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 showing art and interior views as well as a small group of people

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 which includes general coastal views and a beach as well as a small group of people

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

$17
per traveler
Portland Smartphone Audio Tour: Self-Guided Drive
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

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

$10
per traveler
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

$17
per traveler
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS 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.