Cheap Vacations in Harpswell

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4-night Harpswell vacations

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Portland Airport

Hilton Garden Inn Portland Airport

3 out of 5
Price was $597, price is now $503 per person
$503
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $704, price is now $546 per person
$546
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $904, price is now $728 per person
$728
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $770, price is now $636 per person
$636
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
Price was $760, price is now $642 per person
$642
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $714, price is now $607 per person
$607
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Price was $607, price is now $521 per person
$521
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $658, price is now $576 per person
$576
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $774, price is now $679 per person
$679
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Residence Inn Portland Downtown/Waterfront

Residence Inn Portland Downtown/Waterfront

3 out of 5
Price was $642, price is now $566 per person
$566
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
Price was $598, price is now $528 per person
$528
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
Price was $621, price is now $551 per person
$551
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)

6-7 night Harpswell vacations

Price found within the past 48 hours. Click for updated prices.
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
Price was $459, price is now $365 per person
$365
per person
Jan 18 - Jan 24
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Save 100% on your flight
Price was $810, price is now $547 per person
$547
per person
Jan 18 - Jan 24
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
Price was $676, price is now $466 per person
$466
per person
Jan 18 - Jan 24
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Hilton Garden Inn Portland Airport

Hilton Garden Inn Portland Airport

3 out of 5
Price was $617, price is now $452 per person
$452
per person
Jan 18 - Jan 24
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,025, price is now $754 per person
$754
per person
Jan 18 - Jan 24
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Save 100% on your flight
Price was $1,004, price is now $745 per person
$745
per person
Jan 18 - Jan 24
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Price was $570, price is now $436 per person
$436
per person
Jan 18 - Jan 24
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
Price was $749, price is now $578 per person
$578
per person
Jan 18 - Jan 24
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Save 100% on your flight
Price was $931, price is now $724 per person
$724
per person
Jan 18 - Jan 24
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $736, price is now $577 per person
$577
per person
Jan 18 - Jan 24
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
Price was $608, price is now $479 per person
$479
per person
Jan 18 - Jan 24
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $650, price is now $517 per person
$517
per person
Jan 18 - Jan 24
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)

Flight deals to Harpswell

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

Sat, Feb 14 - Sat, Feb 21
TPA
Tampa
PWM
Portland
$162 Roundtrip, found 2 days ago
$162
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Feb 14 from Tampa to Portland, returning Sat, Feb 21, priced at $162 found 2 days ago
Fri, Jan 16 - Tue, Jan 20
MCO
Orlando
PWM
Portland
$166 Roundtrip, found 1 day ago
$166
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jan 16 from Orlando to Portland, returning Tue, Jan 20, priced at $166 found 1 day ago
Fri, Feb 6 - Sat, Feb 7
LGA
New York
PWM
Portland
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Feb 6 from New York to Portland, returning Sat, Feb 7, priced at $167 found 1 day ago

Top rated hotels for your Harpswell vacation

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road South Portland ME
Free Cancellation
Reserve now, pay when you stay
22.61 mi from city center
$67 nightly
The price is $73 total per night
$73 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
When you stay at Tru by Hilton Portland Airport Area in South Portland, you'll be near the airport, just steps from Maine Mall and a 3-minute drive from Nonesuch River Golf Club.
Breakfast included
Free airport shuttle
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Free Cancellation
Reserve now, pay when you stay
18.19 mi from city center
$143 nightly
The price is $158 total per night
$158 total
Dec 15 - Dec 16
Total with taxes and fees
A stay at Portland Regency Hotel & Spa places you in the heart of Portland, steps from Casco Bay and Fore Street Gallery.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
18.36 mi from city center
$145 nightly
The price is $160 total per night
$160 total
Dec 15 - Dec 16
Total with taxes and fees
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Pet friendly
Free WiFi
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.