Search Deals on
Chebeague Island Vacation Packages

Build your package with 2 more options

Leaving from

Going to

Departing

Returning

Travelers

Room 1

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

Add specific hotel dates

Chebeague Island
Maine
United States of America
North America
Hotwire.com

Chebeague Island Flight + Hotel Packages

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

The Wolfeboro Inn

3.5 out of 5

Price was $487, price is now $405 per person

$405

per person

Apr 10 - Apr 12

found 7 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

Book a stay at this beach hotel in Wolfeboro. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Lake Winnipesaukee and Hampshire Pewter Co. are located nearby.

Cliff House Maine

4.5 out of 5

Price was $901, price is now $746 per person

$746

per person

Apr 10 - Apr 12

found 7 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

Book a stay at this luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Perkins Cove and Marginal Way are located nearby.

The Docent’s Collection – Thompson Block

3.5 out of 5

Price was $806, price is now $677 per person

$677

per person

Apr 24 - Apr 26

found 22 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.

Blind Tiger Portland - Danforth Street.

3.5 out of 5

Price was $835, price is now $718 per person

$718

per person

Apr 24 - Apr 26

found 22 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.

Portland Harbor Hotel

4 out of 5

Price was $694, price is now $605 per person

$605

per person

Apr 24 - Apr 26

found 22 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Fore Street Gallery are located nearby.

Inn By The Sea

4 out of 5

Price was $869, price is now $761 per person

$761

per person

Apr 24 - Apr 26

found 22 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.

The McKernan Inn

3 out of 5

Price was $664, price is now $586 per person

$586

per person

Apr 24 - Apr 26

found 22 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

Book a stay at this beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Fort Preble and Portland Harbor Museum are located nearby.

Portland Regency Hotel & Spa

3.5 out of 5

Price was $691, price is now $623 per person

$623

per person

Apr 24 - Apr 26

found 22 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions N.W. Barrett Gallery and Fore Street Gallery are located nearby.