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Harpswell Vacation Packages

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Harpswell Flight + Hotel Packages

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

The Kennebunk Inn

2.5 out of 5
Price was $346, price is now $272 per person
$272
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Stay at this hotel in Kennebunk. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Dock Square and Kennebunk Free Library are located nearby.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $530, price is now $399 per person
$399
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $727, price is now $548 per person
$548
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
River View Resort

River View Resort

2.5 out of 5
Price was $870, price is now $678 per person
$678
per person
Mar 1 - Mar 5
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this motel in Bethel. Enjoy free WiFi, free parking, and 4 outdoor pickleball courts. Our guests praise the helpful staff in our reviews. Popular attractions Sunday River and Bethel Pathway are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $921, price is now $728 per person
$728
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $863, price is now $694 per person
$694
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $566, price is now $456 per person
$456
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Spinneys Guesthouse & Beach Cottages

Spinneys Guesthouse & Beach Cottages

3 out of 5
Price was $635, price is now $520 per person
$520
per person
Jan 25 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.

Harpswell 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
Price was $681, price is now $546 per person
$546
per person
Mar 1 - Mar 5
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $727, price is now $548 per person
$548
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
River View Resort

River View Resort

2.5 out of 5
Price was $870, price is now $678 per person
$678
per person
Mar 1 - Mar 5
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $921, price is now $728 per person
$728
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)

Harpswell Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
Price was $538, price is now $469 per person
$469
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $673, price is now $532 per person
$532
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $739, price is now $624 per person
$624
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
Price was $538, price is now $483 per person
$483
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)

Top Flight Deals

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

Bargain Flight
Tue, Jan 13 - Sun, Jan 18
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$184 Roundtrip, found 1 hour ago
$184
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Tue, Jan 13 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sun, Jan 18, priced at $184 found 1 hour ago
American Airlines
Wed, May 27 - Thu, May 28
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$187 Roundtrip, found 2 hours ago
$187
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Thu, May 28, priced at $187 found 2 hours ago
Bargain Flight
Wed, Feb 18 - Tue, Feb 24
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$199 Roundtrip, found 16 hours ago
$199
Roundtrip
found 16 hours ago
Select Bargain Flight flight, departing Wed, Feb 18 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Tue, Feb 24, priced at $199 found 16 hours ago
Breeze Airways
Fri, Feb 6 - Sun, Feb 8
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Feb 6 from Tampa Intl. to Portland Intl. Jetport, returning Sun, Feb 8, priced at $257 found 1 day ago