
Casco Bay Islands Vacations from $649
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The Latest Casco Bay Islands vacation packages
Price found within the past 48 hours. Click for updated prices.

Waldo Emerson Inn
Price was $721, price is now $649 per person
$649
per person
Jan 6 - Jan 8
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (357 reviews)
Our stay at the Waldo Emerson was nothing short of exceptional! From the moment we arrived, Amelia welcomed us with warm hospitality, and every detail of this charming property made us feel right at home.
The accommodations were comfortable and full of character, and the property itself is absolutely beautiful. Each morning, we looked forward to a delicious, fresh, and thoughtfully prepared breakfast that was the perfect start to our day.
What truly made our experience special were the wonderful sightseeing and dinner recommendations. Amelia and Ron are phenomenal hosts who go above and beyond to ensure their guests have a memorable stay. Their genuine warmth, local knowledge, and attention to detail made our visit to Kennebunkport even more enjoyable.
The Waldo Emerson is an outstanding choice for anyone looking for a charming bed and breakfast in Kennebunkport. We thoroughly enjoyed our stay and would gladly return. We highly recommend it to anyone seeking the perfect combination of comfort, charm, exceptional hospitality, and relaxation!
**A truly wonderful experience from start to finish!**
Reviewed on Oct 18, 2026


Portland Harbor Hotel
Downtown Portland
Price was $1,252, price is now $1,042 per person
$1,042
per person
Dec 26 - Jan 1
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,851 reviews)
Old hotel recently updated. Great location in Old Port in walking distance of restaurants and shop. Very helpful staff. Easy valet parking. They charge a resort fee but you get it back as credit to use for breakfast or at the bar. Great outdoor patio area with gas fire pit. Great vibe for adult travelers.
Reviewed on Nov 14, 2026

The Docent's Collection at 121 Middle Street
Downtown Portland
Price was $880, price is now $782 per person
$782
per person
Dec 19 - Dec 21
found 20 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)
Our only place to stay in Portland!
Reviewed on Nov 14, 2026

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Casco Bay Islands Hotel Deals

The Westin Portland Harborview
157 High St Portland ME
Fully refundable
$91 nightly
The price is $101 total per night from Dec 6 to Dec 7
$101 total
Dec 6 - Dec 7
Total with taxes and fees

Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$76 nightly
The price is $84 total per night from Nov 22 to Nov 23
$84 total
Nov 22 - Nov 23
Total with taxes and fees
8.2/10 Very Good! (1,875 reviews)
"Great location and well maintained"
Reviewed on Nov 14, 2026

Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Nov 22 to Nov 23
$85 total
Nov 22 - Nov 23
Total with taxes and fees
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 Casco Bay Islands Vacation Packages
Casco Bay Islands Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
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