Cheap Vacations in Harpswell

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3-night Harpswell vacations

Price found within the past 48 hours. Click for updated prices.
Ramada by Wyndham Saco/Old Orchard Beach Area

Ramada by Wyndham Saco/Old Orchard Beach Area

2.5 out of 5
Price was $638, price is now $530 per person
$530
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $721, price is now $536 per person
$536
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILM) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,953, price is now $1,455 per person
$1,455
per person
Jun 4 - Jun 7
found 21 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $1,146, price is now $857 per person
$857
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILM) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $988, price is now $740 per person
$740
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILM) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $966, price is now $732 per person
$732
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILM) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,403, price is now $1,096 per person
$1,096
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILM) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,181, price is now $939 per person
$939
per person
Jun 4 - Jun 7
found 21 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $919, price is now $739 per person
$739
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILM) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,151, price is now $927 per person
$927
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILM) to Portland (PWM)
Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Price was $844, price is now $691 per person
$691
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILM) to Portland (PWM)
AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
Price was $1,191, price is now $1,001 per person
$1,001
per person
Jun 4 - Jun 7
found 21 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Portland (PWM)

4-night Harpswell vacations

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Scarborough - Portland

Comfort Inn & Suites Scarborough - Portland

2.5 out of 5
Price was $685, price is now $559 per person
$559
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
Price was $1,300, price is now $917 per person
$917
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,369, price is now $970 per person
$970
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Save 100% on your flight
Price was $1,556, price is now $1,160 per person
$1,160
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Price was $1,392, price is now $1,070 per person
$1,070
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,922, price is now $1,489 per person
$1,489
per person
May 25 - May 29
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $1,163, price is now $933 per person
$933
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

2 out of 5
Price was $1,568, price is now $1,283 per person
$1,283
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Price was $1,702, price is now $1,410 per person
$1,410
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $1,116, price is now $928 per person
$928
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
HomeAwhile

HomeAwhile

4 out of 5
Price was $726, price is now $610 per person
$610
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Longfellow Hotel

Longfellow Hotel

4 out of 5
Price was $1,333, price is now $1,122 per person
$1,122
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)

Flight deals to Harpswell

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

Wed, Jul 8 - Thu, Jul 16
EWR
New York
PWM
Portland
$157 Roundtrip, found 9 hours ago
$157
Roundtrip
found 9 hours ago
Select United flight, departing Wed, Jul 8 from New York to Portland, returning Thu, Jul 16, priced at $157 found 9 hours ago
Wed, Jul 8 - Tue, Jul 14
LGA
New York
PWM
Portland
$157 Roundtrip, found 22 hours ago
$157
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Wed, Jul 8 from New York to Portland, returning Tue, Jul 14, priced at $157 found 22 hours ago
Tue, Jun 2 - Sat, Jun 6
JFK
New York
PWM
Portland
$161 Roundtrip, found 9 hours ago
$161
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Tue, Jun 2 from New York to Portland, returning Sat, Jun 6, priced at $161 found 9 hours ago

Top rated hotels for your Harpswell vacation

1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage

Harpswell ME
2.41 mi from city center
Get rates
With a stay at this apartment in Harpswell, you'll be on the waterfront, just steps from Casco Bay and a 5-minute drive from Mitchell Field.
Kitchen
Pet friendly
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Free Cancellation
Reserve now, pay when you stay
18.75 mi from city center
$122 nightly
The price is $135 total per night
$135 total
Apr 22 - Apr 23
Total with taxes and fees
With a stay at The Westin Portland Harborview, you'll be centrally located in Portland, steps from State Theatre and Portland Museum of Art.
Spa
Pet friendly
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
$170 nightly
The price is $188 total per night
$188 total
Apr 26 - Apr 27
Total with taxes and fees
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
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.

Top Picks

^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.