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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.
Best Western Freeport Inn

Best Western Freeport Inn

3 out of 5
Price was $280, price is now $238 per person
$238
per person
Mar 17 - Mar 21
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Freeport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LL Bean Flagship Store and Eartha are located nearby.
The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $558, price is now $343 per person
$343
per person
Mar 17 - Mar 21
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
Price was $742, price is now $467 per person
$467
per person
Feb 18 - Feb 21
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Freeport. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,144, price is now $805 per person
$805
per person
Mar 17 - Mar 21
found 2 hours 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.
Spinneys Guesthouse & Beach Cottages

Spinneys Guesthouse & Beach Cottages

3 out of 5
Save 100% on your flight
Price was $399, price is now $308 per person
$308
per person
Mar 17 - Mar 21
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this beach guesthouse in Phippsburg. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Popham Beach and Fort Popham State Historic Site are located nearby.
Inn on Shore Road

Inn on Shore Road

2 out of 5
Save 100% on your flight
Price was $605, price is now $487 per person
$487
per person
Mar 17 - Mar 21
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this inn in Ogunquit. Enjoy free breakfast, free WiFi, and housekeeping. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $816, price is now $671 per person
$671
per person
Feb 13 - Feb 15
found 2 hours 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.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,127, price is now $953 per person
$953
per person
Feb 13 - Feb 15
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) 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.

Chebeague Island Vacation Packages 3-4 Night Stays

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

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $558, price is now $343 per person
$343
per person
Mar 17 - Mar 21
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
Price was $742, price is now $467 per person
$467
per person
Feb 18 - Feb 21
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
Price was $789, price is now $505 per person
$505
per person
Feb 18 - Feb 21
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $647, price is now $434 per person
$434
per person
Mar 1 - Mar 5
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)

Chebeague Island Vacation Packages 5-7 Night Stays

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

The Westin Portland Harborview

4 out of 5
Downtown Portland
Price was $871, price is now $690 per person
$690
per person
Mar 13 - Mar 19
found 19 hours ago
Roundtrip non-stop 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
Price was $1,148, price is now $848 per person
$848
per person
Mar 13 - Mar 19
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $965, price is now $764 per person
$764
per person
Mar 13 - Mar 19
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $1,019, price is now $814 per person
$814
per person
Mar 13 - Mar 19
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)

Top Flight Deals

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

American Airlines
Wed, May 27 - Tue, Jun 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$183 Roundtrip, found 12 hours ago
$183
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Jun 2, priced at $183 found 12 hours ago
Delta
Tue, Feb 3 - Sat, Feb 7
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Feb 3 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Feb 7, priced at $183 found 1 day ago
American Airlines
Tue, Feb 17 - Tue, Feb 24
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 17 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Tue, Feb 24, priced at $189 found 1 day ago
American Airlines
Fri, Jan 23 - Sat, Jan 24
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$194 Roundtrip, found 5 days ago
$194
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Jan 23 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sat, Jan 24, priced at $194 found 5 days ago