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Chebeague Island Vacation Packages

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Chebeague Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $367, price is now $279 per person
$279
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Portland Stage are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
Price was $504, price is now $286 per person
$286
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Save 100% on your flight
Price was $452, price is now $321 per person
$321
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Save 100% on your flight
Price was $481, price is now $344 per person
$344
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,341, price is now $972 per person
$972
per person
Feb 26 - Mar 1
found 6 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.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $700, price is now $527 per person
$527
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
Price was $366, price is now $281 per person
$281
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Maine Jewish Museum and Maine Narrow Gauge Railroad Company and Museum are located nearby.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $716, price is now $555 per person
$555
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Kennebunkport Village Green are located nearby.

Chebeague Island Vacation Packages 3-4 Night Stays

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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $504, price is now $286 per person
$286
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $452, price is now $321 per person
$321
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $481, price is now $344 per person
$344
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was $1,341, price is now $972 per person
$972
per person
Feb 26 - Mar 1
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

Chebeague Island Vacation Packages 5-7 Night Stays

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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $962, price is now $579 per person
$579
per person
Mar 3 - Mar 9
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $1,052, price is now $729 per person
$729
per person
Mar 3 - Mar 9
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $915, price is now $645 per person
$645
per person
Mar 3 - Mar 9
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $891, price is now $652 per person
$652
per person
Mar 3 - Mar 9
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Delta
Wed, May 27 - Tue, Jun 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$187 Roundtrip, found 3 days ago
$187
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Jun 2, priced at $187 found 3 days ago
American Airlines
Tue, Feb 17 - Tue, Feb 24
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$204 Roundtrip, found 4 hours ago
$204
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Tue, Feb 17 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Tue, Feb 24, priced at $204 found 4 hours ago
American Airlines
Thu, Apr 9 - Mon, Apr 13
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$209 Roundtrip, found 3 days ago
$209
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Apr 9 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Mon, Apr 13, priced at $209 found 3 days ago
Bargain Flight
Wed, May 27 - Wed, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$249 Roundtrip, found 6 days ago
$249
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Wed, May 27 from Hartsfield-Jackson Atlanta Intl. to Portland Intl. Jetport, returning Wed, Jun 3, priced at $249 found 6 days ago