Stroudwater Vacations from $448

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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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $585, price is now $448 per person
$448
per person
Nov 20 - Nov 23
found 21 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
9.2/10 Wonderful! (1,581 reviews)
Nice hotel within walking distance of everything downtown.

Reviewed on Oct 9, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,160, price is now $810 per person
$810
per person
Nov 20 - Nov 23
found 21 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
9.4/10 Exceptional! (1,007 reviews)
The views were absolutely breath taking every where on the property. Staff extremely friendly and caring. Night time entertainment was a plus.

Reviewed on Oct 8, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,097, price is now $821 per person
$821
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.8/10 Exceptional! (79 reviews)
Great spot, large space, cool design, clean, easy to walk all over town.

Reviewed on Oct 1, 2025

InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $1,042, price is now $798 per person
$798
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (347 reviews)
Nice and convenient

Reviewed on Oct 3, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,268, price is now $982 per person
$982
per person
Nov 20 - Nov 23
found 21 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
9.4/10 Exceptional! (281 reviews)
Absolutely 5 star. Best bed I’ve slept in at a hotel bar none.

Reviewed on Sep 10, 2025

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

5 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

Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $93 total per night from Nov 2 to Nov 3
$93 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (1,115 reviews)
"Fine for a night on our way to the outer parts of Maine"

Reviewed on Oct 6, 2025

Clarion Hotel Portland
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
$90 nightly
The price is $98 total per night from Oct 19 to Oct 20
$98 total
Oct 19 - Oct 20
Total with taxes and fees
7.4/10 Good! (288 reviews)
"It was convenient right off the highway. The room was clean and comfortable and the staff was friendly"

Reviewed on Oct 2, 2025

Germaine Inn South Portland
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $115 total per night from Nov 2 to Nov 3
$115 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (1,013 reviews)
"A renovation would be good."

Reviewed on Oct 7, 2025

Fireside Inn & Suites Portland
See all 2,399 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.
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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

Port City Light Cruise

Port City Lights Cruise

$41
per adult
100% of travellers recommend
Port City Lights Cruise
Portland: Maine Lighthouses Sightseeing Cruise with Drinks

Portland: Maine Lighthouses Sightseeing Cruise with Drinks

$69
per adult
Portland: Maine Lighthouses Sightseeing Cruise with Drinks
Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

$69
per adult
Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks
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.