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.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $992, price is now $790 per person
$790
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Save 100% on your flight
Price was $2,760, price is now $1,948 per person
$1,948
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Price was $2,315, price is now $1,747 per person
$1,747
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $2,287, price is now $1,884 per person
$1,884
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Dormir

Dormir

3 out of 5
Price was $1,132, price is now $964 per person
$964
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Saco Bay Hotel

Saco Bay Hotel

2.5 out of 5
Price was $933, price is now $801 per person
$801
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
The Francis

The Francis

3.5 out of 5
Price was $1,451, price is now $1,249 per person
$1,249
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Fortland Island Campground

Fortland Island Campground

1 out of 5
Price was $2,203, price is now $1,915 per person
$1,915
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $916, price is now $797 per person
$797
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) 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 $985, price is now $858 per person
$858
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $1,787, price is now $1,560 per person
$1,560
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,199, price is now $1,055 per person
$1,055
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)

4-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 $696, price is now $644 per person
$644
per person
Oct 17 - Oct 21
found 19 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Save 100% on your flight
Price was $2,248, price is now $1,643 per person
$1,643
per person
Oct 17 - Oct 21
found 19 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Save 100% on your flight
Price was $2,662, price is now $2,068 per person
$2,068
per person
Oct 17 - Oct 21
found 19 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
Price was $965, price is now $773 per person
$773
per person
Oct 17 - Oct 21
found 19 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) 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 $1,607, price is now $1,302 per person
$1,302
per person
Oct 17 - Oct 21
found 19 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $1,822, price is now $1,575 per person
$1,575
per person
Oct 17 - Oct 21
found 19 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Price was $1,358, price is now $1,209 per person
$1,209
per person
Oct 17 - Oct 21
found 19 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)
Dormir

Dormir

3 out of 5
Price was $1,023, price is now $914 per person
$914
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,889, price is now $1,704 per person
$1,704
per person
Oct 17 - Oct 21
found 19 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)
Longfellow Hotel

Longfellow Hotel

4 out of 5
Price was $1,604, price is now $1,473 per person
$1,473
per person
Oct 17 - Oct 21
found 19 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)
The Francis

The Francis

3.5 out of 5
Price was $1,314, price is now $1,208 per person
$1,208
per person
Oct 17 - Oct 21
found 19 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
Price was $1,226, price is now $1,135 per person
$1,135
per person
Oct 17 - Oct 21
found 19 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Portland (PWM)

6-7 night Harpswell vacations

Price found within the past 48 hours. Click for updated prices.
Grand Beach Inn

Grand Beach Inn

3 out of 5
Price was $885, price is now $775 per person
$775
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Save 100% on your flight
Price was $3,491, price is now $2,387 per person
$2,387
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Save 100% on your flight
Price was $5,238, price is now $3,779 per person
$3,779
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
Price was $1,557, price is now $1,154 per person
$1,154
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) 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 $2,618, price is now $1,984 per person
$1,984
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Save 100% on your flight
Price was $3,155, price is now $2,542 per person
$2,542
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
Price was $3,274, price is now $2,761 per person
$2,761
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Price was $2,296, price is now $1,960 per person
$1,960
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Longfellow Hotel

Longfellow Hotel

4 out of 5
Price was $2,709, price is now $2,351 per person
$2,351
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
Price was $1,008, price is now $899 per person
$899
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $2,102, price is now $1,901 per person
$1,901
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Price was $1,020, price is now $927 per person
$927
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)

Flight deals to Harpswell

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

Tue, Oct 6 - Wed, Oct 7
DCA
Washington
PWM
Portland
$240 Roundtrip, found 19 hours ago
$240
Roundtrip
found 19 hours ago
Select Bargain Flight flight, departing Tue, Oct 6 from Washington to Portland, returning Wed, Oct 7, priced at $240 found 19 hours ago
Wed, Sep 16 - Wed, Sep 23
TPA
Tampa
PWM
Portland
$254 Roundtrip, found 3 days ago
$254
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Sep 16 from Tampa to Portland, returning Wed, Sep 23, priced at $254 found 3 days ago
Wed, Sep 16 - Thu, Sep 17
MCO
Orlando
PWM
Portland
$260 Roundtrip, found 3 days ago
$260
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Sep 16 from Orlando to Portland, returning Thu, Sep 17, priced at $260 found 3 days ago

Top rated hotels for your Harpswell vacation

Oceanfront Studio w/ Private Dock in Harpswell!

Oceanfront Studio w/ Private Dock in Harpswell!

3 out of 5
Harpswell ME
0.91 mi from city center
Get rates
Located in Harpswell, this apartment is a 1-minute drive from Casco Bay and 9 minutes from Bailey Island Bridge.
Kitchen
Free WiFi
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Free Cancellation
21.97 mi from city center
$88 nightly
The price is $96 total per night
$96 total
Sep 13 - Sep 14
Total with taxes and fees
With a stay at Quality Inn & Suites South Portland in South Portland (Sunset Park), you'll be a 4-minute drive from Maine Mall and 6 minutes from Thompson's Point.
Breakfast included
Pet friendly
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

3.5 out of 5
80 John Roberts Rd. South Portland ME
Free Cancellation
22.41 mi from city center
$123 nightly
The price is $134 total per night
$134 total
Sep 7 - Sep 8
Total with taxes and fees
When you stay at Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel in South Portland, you'll be in a shopping district, a 1-minute drive from Maine Mall and 8 minutes from Thompson's Point.
Breakfast included
Free airport shuttle
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.

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.