Harpswell Vacations from $401

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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.

The Latest Harpswell vacation packages

Price found within the past 48 hours. Click for updated prices.
Dormir

Dormir

3 out of 5
Price was $482, price is now $401 per person
$401
per person
Dec 2 - Dec 5
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9/10 Wonderful! (1,004 reviews)
Everything was good

Reviewed on Nov 2, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was $717, price is now $590 per person
$590
per person
Dec 3 - Dec 6
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $564, price is now $476 per person
$476
per person
Dec 28 - Dec 30
found 12 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.6/10 Excellent! (1,007 reviews)
The people who worked at Meadowmere were very nice! I thought it needed a little updating. The TV wasn’t easy to find our way around. The pool wasn’t heated so I didn’t go in. We were supposed to have a continental breakfast included but we went down at 9 am this morning before leaving and the doors were locked. Yesterday it was open early. The location was good, close to the shops but we probably won’t stay again.

Reviewed on Nov 2, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $603, price is now $509 per person
$509
per person
Dec 3 - Dec 6
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (1,851 reviews)
Nice design, exceptional staff and a convenient location in the Old Port neighborhood. Fitness room includes Pelotons.

Reviewed on Nov 2, 2026

The Kendall Inn

The Kendall Inn

3.5 out of 5
Price was $572, price is now $484 per person
$484
per person
Dec 2 - Dec 5
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.8/10 Exceptional! (166 reviews)
We truly enjoyed our stay at the Kendall Inn. The staff were very welcoming and their cooking was excellent. They even accommodated my gluten allergy at meals. Would highly recommend staying here!

Reviewed on Oct 31, 2026

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Stay near popular Harpswell attractions

Ash Cove Pottery

9.4/10 (3 reviews)
Ash Cove Pottery offers handcrafted stoneware inspired by Maine's coastal beauty. Browse signature Double Dip Dinghies and functional pieces in a working studio with bay views as artists create maritime treasures.
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Harpswell Hotel Deals

Oceanfront Studio w/ Private Dock in Harpswell!

Oceanfront Studio w/ Private Dock in Harpswell!

3 out of 5
Harpswell ME
Get rates
Oceanfront Studio w/ Private Dock in Harpswell!
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $119 total per night from Nov 22 to Nov 23
$119 total
Nov 22 - Nov 23
Total with taxes and fees
The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
$81 nightly
The price is $89 total per night from Nov 8 to Nov 9
$89 total
Nov 8 - Nov 9
Total with taxes and fees
Clarion Hotel Portland Airport ME
See all 2,221 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.

Find the Best Harpswell Vacation Packages

Harpswell Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Top Sights
Thomas Point Beach, Wolfes Neck Woods State Park and Maine State Music Theater

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Frequently asked questions

How much does a Harpswell vacation package cost?
You'll find cheap prices from $401 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?
If you're hoping to snag a cheap Harpswell vacation package, consider visiting in November, December and January. You'll usually find better rates on accommodations and flights during these months — ideal for a budget-friendly break.
How many days is enough for Harpswell?
The ideal duration for your Harpswell vacation depends on what you'd like to do. Usually, a few days to a week will give you time to hit all the top sights and discover some hidden spots along the way.
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 your dates: What you plan to do in Harpswell and your favorite season can help you decide when to go.
  2. Set your budget: Factor in costs like flights, food and transportation when calculating how much to set aside for your trip to Harpswell. Then, select a property that suits your budget, whether that's a wallet-friendly option or a lavish retreat.
  3. Use Expedia's trip planning tool to explore Harpswell: Research every aspect of your trip to Harpswell with this comprehensive planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide how long to go away for: Now that you know more about Harpswell, you can figure out the perfect length of your break. Pull together a draft itinerary and allocate enough time to get through everything on your must-do list.
  5. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Harpswell vacation package that brings all your bookings together.
  6. Book experiences or activities ahead of time: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on the highlights of Harpswell. Find all the fun things to do in Harpswell in Harpswell with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Harpswell vacation packages?
Secure your ideal getaway to Harpswell with help from our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up cheap deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.