Cheap Vacations in Harpswell

Choose two or more items and save on your trip:

3-night Harpswell vacations

Price found within the past 48 hours. Click for updated prices.
River View Resort

River View Resort

2.5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 7
found 15 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 7
found 15 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 7
found 15 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 7
found 15 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 7
found 15 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 7
found 15 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
The Press Hotel, Marriott Autograph Collection

The Press Hotel, Marriott Autograph Collection

4 out of 5
per person
Jul 15 - Jul 18
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Microtel Inn & Suites by Wyndham York

Microtel Inn & Suites by Wyndham York

2 out of 5
per person
Jul 4 - Jul 7
found 15 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Ocean Gate Resort

Ocean Gate Resort

3 out of 5
per person
Jul 4 - Jul 7
found 15 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Residence Inn by Marriott Portland Downtown Waterfront

Residence Inn by Marriott Portland Downtown Waterfront

3 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 7
found 15 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
per person
Jul 4 - Jul 7
found 15 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 7
found 15 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)

4-night Harpswell vacations

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
per person
Jul 13 - Jul 17
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
per person
Jul 13 - Jul 17
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Save 100% on your flight
per person
Jul 13 - Jul 17
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Residence Inn by Marriott Portland Downtown Waterfront

Residence Inn by Marriott Portland Downtown Waterfront

3 out of 5
Save 100% on your flight
per person
Jul 13 - Jul 17
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
Save 100% on your flight
per person
Jul 13 - Jul 17
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Save 100% on your flight
per person
Jul 13 - Jul 17
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
Save 100% on your flight
per person
Jul 13 - Jul 17
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Save 100% on your flight
per person
Jul 13 - Jul 17
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Longfellow Hotel

Longfellow Hotel

3 out of 5
Save 100% on your flight
per person
Jul 13 - Jul 17
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
per person
Jul 13 - Jul 17
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Aloft Portland Downtown Waterfront ME

Aloft Portland Downtown Waterfront ME

3 out of 5
per person
Jul 13 - Jul 17
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Holiday Inn Portland-By the Bay, an IHG Hotel

Holiday Inn Portland-By the Bay, an IHG Hotel

3 out of 5
per person
Jul 13 - Jul 17
found 23 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)

5-night Harpswell vacations

Price found within the past 48 hours. Click for updated prices.
River View Resort

River View Resort

2.5 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Ogunquit Hotel & Suites

Ogunquit Hotel & Suites

2 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Save 100% on your flight
per person
Jul 14 - Jul 19
found 24 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
per person
Jul 14 - Jul 19
found 24 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Ocean Gate Resort

Ocean Gate Resort

3 out of 5
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Residence Inn by Marriott Portland Downtown Waterfront

Residence Inn by Marriott Portland Downtown Waterfront

3 out of 5
per person
Jul 14 - Jul 19
found 24 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
per person
Jul 14 - Jul 19
found 24 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Save 100% on your flight
per person
Jul 14 - Jul 19
found 24 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
per person
Jul 14 - Jul 19
found 24 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
per person
Jul 14 - Jul 19
found 24 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
per person
Jul 14 - Jul 19
found 24 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)

Flight deals to Harpswell

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

Tue, Jun 25 - Tue, Jul 16
RDU
Raleigh
PWM
Portland
$68 Roundtrip, found 9 hours ago
$68
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Tue, Jun 25 from Raleigh to Portland, returning Tue, Jul 16, priced at $68 found 9 hours ago
Tue, Jun 11 - Thu, Jun 13
PHL
Philadelphia
PWM
Portland
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Jun 11 from Philadelphia to Portland, returning Thu, Jun 13, priced at $68 found 6 days ago
Tue, Sep 10 - Wed, Sep 11
ATL
Atlanta
PWM
Portland
$110 Roundtrip, found 4 days ago
$110
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Sep 10 from Atlanta to Portland, returning Wed, Sep 11, priced at $110 found 4 days ago

Top rated hotels for your Harpswell vacation

Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

3.5 out of 5
80 John Roberts Rd., South Portland, ME
Free Cancellation
Reserve now, pay when you stay
22.41 mi from city center
The price is $89 per night
$89
per night
Jun 9 - Jun 10
When you stay at Casco Bay Hotel, Ascend Hotel Collection in South Portland, you'll be in a shopping district, a 1-minute drive from Maine Mall and 9 minutes from Thompson's Point.
Pet friendly
Breakfast included
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
The price is $233 per night
$233
per night
Jun 9 - Jun 10
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, within a 5-minute drive of State Theatre and Thompson's Point.
Pet friendly
Breakfast available
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
18.44 mi from city center
The price is $331 per night
$331
per night
Jun 9 - Jun 10
With a stay at Canopy by Hilton Portland Waterfront in Portland (Downtown Portland), you'll be within a 5-minute drive of State Theatre and Thompson's Point.
Pet friendly
Breakfast available
Don't see what you're looking for?
See all available properties in Harpswell
View all properties
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.