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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 Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
Price was $921, price is now $732 per person
$732
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,187, price is now $888 per person
$888
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Price was $1,857, price is now $1,427 per person
$1,427
per person
Oct 19 - Oct 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 Thompson's Point and Portland Head Light are located nearby.

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,999, price is now $1,570 per person
$1,570
per person
Oct 19 - Oct 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 Thompson's Point and Portland Head Light are located nearby.
Staff was great, but rooms and amenities were incredibly dated. The bathroom had no ventilation, a very old shower, and mediocre product options. The rooms were very bare bones and not warm or inviting. There was nothing all that special about this property and certainty not worth the nightly rate.

Reviewed on Sep 6, 2026

Nautical Mile

Nautical Mile

2.5 out of 5
Price was $1,066, price is now $846 per person
$846
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this aparthotel in Wells. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ogunquit Beach and Wells Beach are located nearby.
Bel endroit où séjourner! Tout près de Well’s Beach.

Reviewed on Jul 27, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Save 100% on your flight
Price was $2,508, price is now $2,019 per person
$2,019
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.

Nonantum Resort

Nonantum Resort

3.5 out of 5
Price was $1,138, price is now $925 per person
$925
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Portland (PWM)
Stay at this hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dock Square and Wells Beach are located nearby.

Dormir

Dormir

3 out of 5
Price was $1,088, price is now $885 per person
$885
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
Book a stay at this business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sebago Lake and Seacoast Adventure are located nearby.

Harpswell Vacation Packages 3-4 Night Stays

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

The Wolfeboro Inn

3.5 out of 5
Price was $921, price is now $732 per person
$732
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Downtown Portland
Price was $1,857, price is now $1,427 per person
$1,427
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,239, price is now $972 per person
$972
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,999, price is now $1,570 per person
$1,570
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)

Harpswell Vacation Packages 5-7 Night Stays

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

The Meadowmere Resort

2.5 out of 5
Price was $1,187, price is now $888 per person
$888
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,218, price is now $1,566 per person
$1,566
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was $1,411, price is now $1,056 per person
$1,056
per person
Dec 1 - Dec 6
just found
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $3,337, price is now $2,504 per person
$2,504
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip 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.

Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 3 hours ago
$185
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $185 found 3 hours ago
Bargain Flight
Fri, Sep 11 - Wed, Sep 30
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$237 Roundtrip, just found
$237
Roundtrip
just found
Select Bargain Flight flight, departing Fri, Sep 11 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Sep 30, priced at $237 just found
Breeze Airways
Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$266 Roundtrip, found 11 hours ago
$266
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Wed, Feb 24 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Feb 27, priced at $266 found 11 hours ago
United
Sat, Nov 14 - Wed, Dec 2
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$299 Roundtrip, just found
$299
Roundtrip
just found
Select United flight, departing Sat, Nov 14 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, Dec 2, priced at $299 just found