Orrs Island Vacations from $650

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Your Orrs Island Vacation

Spend less time travel planning and more time having memorable adventures with a Orrs Island vacation package. The neighborhood of Harpswell, which is good for nature and culture, makes a fantastic base for your city getaway. Like to get out and explore? Bailey Island Bridge, Lands End Gift Shop and Eagle Island are among the top places to visit during your trip to Orrs Island. Your Orrs Island vacation is just clicks away. Search hotels, airfares and more on Expedia for an adventure that's tailored to suit your style.

The Latest Orrs Island 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 $1,000, price is now $650 per person
$650
per person
Apr 1 - Apr 6
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Reduce noise from patrons near elevator and coffee area on second floor, very loud

Reviewed on Jan 10, 2026

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $1,201, price is now $864 per person
$864
per person
Apr 1 - Apr 6
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Room and amenities were great and ease of access to both the room and surrounding businesses is ideal.

Reviewed on Jan 10, 2026

The McKernan Inn

The McKernan Inn

3 out of 5
Price was $1,019, price is now $756 per person
$756
per person
Apr 1 - Apr 6
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on Dec 27, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was $1,778, price is now $1,378 per person
$1,378
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Loved the hotel had a great time with a group of friends

Reviewed on Jan 12, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $906, price is now $703 per person
$703
per person
Apr 1 - Apr 6
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,512 reviews)
Room is awesome , love the hotel.

Reviewed on Jan 12, 2026

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Discover the most popular places to visit in Orrs Island

Paddleworks

Enjoy an outing to Paddleworks during your stay in Orrs Island. Wander the seaside and beaches in the area.

Paddleworks

Orrs Island Hotel Deals

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
$78 nightly
The price is $87 total per night from Jan 15 to Jan 16
$87 total
Jan 15 - Jan 16
Total with taxes and fees
8/10 Very Good! (1,322 reviews)
Very nice

Reviewed on Jan 11, 2026

Clarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $117 total per night from Feb 4 to Feb 5
$117 total
Feb 4 - Feb 5
Total with taxes and fees
8.8/10 Excellent! (1,008 reviews)
Room was clean and had all amenities.

Reviewed on Jan 6, 2026

The Westin Portland Harborview
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
$138 nightly
The price is $152 total per night from Jan 25 to Jan 26
$152 total
Jan 25 - Jan 26
Total with taxes and fees
9.4/10 Exceptional! (1,573 reviews)
Room is awesome , love the hotel.

Reviewed on Jan 12, 2026

Portland Regency Hotel & Spa
See all 1,769 properties in Orrs Island
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.

Find the Best Orrs Island Vacation Packages

Orrs Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Top Sights
Thomas Point Beach, Wolfes Neck Woods State Park and Maine State Music Theater

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Frequently asked questions

How much does an Orrs Island vacation package cost?
You'll find cheap prices from $650 on Expedia for your Orrs Island getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Orrs Island costs.
What are the cheapest months to go to Orrs Island?
November, December and January are great times to search for cheap Orrs Island vacation packages. Traveling in less busy months means you can generally find lower prices on flights and accommodations.
How many days is enough for Orrs Island?
With a well-organized itinerary, you can easily hit the main Orrs Island sights in a few days. But if you prefer to discover hidden gems or go on day tours, think about booking your Orrs Island vacation for longer.
How to find the best Orrs Island package deals?
Use Expedia's filter tool to help you find some fabulous Orrs Island package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Orrs Island package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book an Orrs Island vacation as a package?
You can enjoy significant savings on your Orrs Island break by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Orrs Island?
If you're considering an impromptu Orrs Island getaway, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Orrs Island vacation packages?
Jet off on your ideal getaway to Orrs Island with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or hold off until the next payday — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stick to your budget and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.