Harpswell Vacation Packages

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Your Harpswell Vacation

With one of our vacation packages to Harpswell, you'll have infinite opportunities for fun and relaxation. There's loads to enjoy, including its coastal scenery and spectacular views. Want to explore your surroundings? Thomas Point Beach, Bailey Island Bridge and Ragged Island are among the top-rated places to visit during a trip to Harpswell. A couple of clicks is all it takes to create the perfect Harpswell vacation on Expedia.

Top Harpswell Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Microtel Inn & Suites By Wyndham Windham

Microtel Inn & Suites By Wyndham Windham

3 out of 5
per person
Jun. 30 - Jul. 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (1,000 reviews)
Upon entering greeted by friendly staff, clean and inviting, check-in was quick and easy!

Reviewed on Apr. 7, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Jun. 30 - Jul. 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,475 reviews)
This hotel was placed perfectly within Downtown Portland and was very clean and all of the employees were friendly.

Reviewed on Apr. 26, 2025

Chebeague Island Inn

Chebeague Island Inn

4 out of 5
per person
Jun. 30 - Jul. 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (70 reviews)
Met our expectations

Reviewed on Sep. 9, 2024

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
per person
Jun. 30 - Jul. 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (141 reviews)
Great, enjoyed our stay.

Reviewed on Apr. 24, 2025

Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
per person
Jun. 30 - Jul. 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (168 reviews)
Great stay at Diamond Inn. Highly recommend!

Reviewed on Oct. 18, 2024

Ready to book your vacation to Harpswell?

 

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Harpswell Hotel Deals

1 room luxury ocean front studio cottage
1 room luxury ocean front studio cottage
Harpswell
9.4/10 Exceptional! (131 reviews)
"Very clean, amazinv views, perfect weekend!!!!"

Reviewed on Nov. 17, 2024

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1 room luxury ocean front studio cottage
Beautiful House just a step from ocean
Beautiful House just a step from ocean
Harpswell
9/10 Wonderful! (2 reviews)
Beautiful View
"Lovely place for a couple and a child. Master bedroom was lovely. Water would not allow bathing but shower was ok in hall bath. The downstairs sleeping for two adults was a little difficult. Would have been nice to know upfront that the water was not potable. Nice touches with the set dining table ..."

Reviewed on Oct. 13, 2023

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Beautiful House just a step from ocean
The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from May 26 to May 27
CA $187
CA $210 total
includes taxes & fees
May 26 - May 27
8.8/10 Excellent! (1,001 reviews)
"Lovely hotel for those who wish to be removed from the hustle of the Old Port. Friendly, clean, new and upscale facility. This area of Portland is a bit gritty--not at all dangerous Bar at the top of the building is very good with wonderful views."

Reviewed on Apr. 22, 2025

The Westin Portland Harborview
See all 2,022 properties in Harpswell
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.

All Inclusive Vacations

All Inclusive Vacations

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Frequently asked questions

How much does a Harpswell vacation package cost?
You’ll find cheap prices from CA $1,129 on Expedia for your Harpswell break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Harpswell costs.
What are the cheapest months to go to Harpswell?
Plan your trip for the off-season and you’re likely to get cheap Harpswell vacation packages. Remember that school vacation periods and major events and festivals can impact prices, so do a little research before booking.
How many days is enough for Harpswell?
Usually, a handful of days is enough to tick off the main attractions during your Harpswell vacation. However, if you’d like to have more time to relax or take day trips, think about extending your itinerary.
How to find the best Harpswell package deals?
Use Expedia’s handy filters to help you find some unbeatable Harpswell package deals. When you start your search, just set your maximum budget and then sort the results by “Price: low to high.” If you want to save, plan your adventure for midweek, or search for Harpswell package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it’s usually best to book your vacation package as soon as possible.
Is it cheaper to book a Harpswell vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can personalize your Harpswell escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Harpswell?
If you’ve got your Harpswell travel dates finalized, book as soon as you can to grab some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Harpswell?

  1. Choose when to get away: Check your schedule and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to escape to Harpswell.
  2. Budget wisely: As well as the cost of your stay, you should factor in other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected expenses that may arise during your trip to Harpswell.
  3. Decide how long to go for: Now that you know more about Harpswell, you can work out the ideal length of your break. Create a rough plan and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalized Harpswell vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.