Cousins Island Vacations from $471

Name: Portland Regency Hotel & Spa
Price range: $148 total
Rating: 9.4

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The Latest Cousins Island vacation packages

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

The Westin Portland Harborview

Downtown Portland

$471

per person

Mar 18 - Mar 22

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

8.8/10 Excellent! (1,001 reviews)

Spotless rooms, very roomy bathrooms, great staff

Reviewed on Dec 29, 2025

The Docent’s Collection – Thompson Block

Downtown Portland

$610

per person

Mar 18 - Mar 22

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.6/10 Exceptional! (249 reviews)

This was a great stay! Had everything we wanted. Location was excellent.

Reviewed on Dec 24, 2025

Portland Harbor Hotel

Downtown Portland

$510

per person

Mar 18 - Mar 22

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.2/10 Wonderful! (1,668 reviews)

Entire hotel, room, staff were incredible!

Reviewed on Jan 4, 2026

Portland Regency Hotel & Spa

Downtown Portland

$536

per person

Mar 18 - Mar 22

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.4/10 Exceptional! (1,512 reviews)

We stay annually, and look it!! Conveniently located, that spa is wonderful, room service is always fant

Reviewed on Jan 3, 2026

Inn By The Sea

$741

per person

Mar 18 - Mar 22

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.4/10 Exceptional! (288 reviews)

Room was ready early friendly staff and room is better than expected

Reviewed on Nov 16, 2025

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See all available trips from Columbus to Cousins Island

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Discover the most popular places to visit in Cousins Island

Little John Island Preserve

Explore the great outdoors at Little John Island Preserve, a lovely green space in Yarmouth. Stroll along the area's waterfront or experience its entertainment choices.

Eartha

You can find out about the history of Yarmouth when you stop by Eartha. Wander the area's waterfront or simply enjoy one of its top-notch restaurants.

Clay Play

You can spend time exploring the galleries in Clay Play in Yarmouth. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Cousins Island Hotel Deals

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Fully refundableReserve now, pay when you stay

$78 nightly

$87 total

Jan 7 - Jan 8

Total with taxes and fees

7.8/10 Good! (1,307 reviews)

The airport shuttle was very convenient and appreciated on an early and snowy Christmas Eve morning. Night and morning desk staff were very helpful and friendly.

Reviewed on Dec 26, 2025

The Westin Portland Harborview

157 High St Portland ME

Fully refundableReserve now, pay when you stay

$98 nightly

$108 total

Jan 21 - Jan 22

Total with taxes and fees

8.8/10 Excellent! (1,002 reviews)

Staff was so friendly and had great dining recommendations. Room was super clean. Hotel was quiet and located in a perfect spot around the corner from the comedy show we went to see. Everything was so nice and good luck to the ginger bread house decoration competitors! We hope our choice wins!

Reviewed on Dec 22, 2025

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Fully refundableReserve now, pay when you stay

$134 nightly

$148 total

Jan 6 - Jan 7

Total with taxes and fees

9.4/10 Exceptional! (1,558 reviews)

Perfect location- lovely little hotel bar, nice room - friendly staff

Reviewed on Dec 29, 2025

See all 1,618 properties in Cousins 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.