Harpswell Vacations from $513

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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 $643, price is now $513 per person
$513
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
9/10 Wonderful! (1,004 reviews)
I love this place. This is the 2nd time I've stayed here. It's clean, quiet, well located. The staff is friendly and helpful. I would recommend it to anyone.

Reviewed on Nov 3, 2026

Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Price was $664, price is now $539 per person
$539
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Portland (PWM)
8.8/10 Excellent! (65 reviews)
Very unique and fun history.

Reviewed on Oct 27, 2026

Snowvillage Inn

Snowvillage Inn

4 out of 5
Price was $1,799, price is now $1,469 per person
$1,469
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Portland (PWM)
8.8/10 Excellent! (319 reviews)
A quaint property with tons of hidden gems. Nestled on a mountainside, Snowvillage

Reviewed on Oct 24, 2026

Waldo Emerson Inn

Waldo Emerson Inn

3 out of 5
Price was $660, price is now $549 per person
$549
per person
Jan 4 - Jan 7
found 22 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
8.8/10 Excellent! (357 reviews)
Our stay at the Waldo Emerson was nothing short of exceptional! From the moment we arrived, Amelia welcomed us with warm hospitality, and every detail of this charming property made us feel right at home. The accommodations were comfortable and full of character, and the property itself is absolutely beautiful. Each morning, we looked forward to a delicious, fresh, and thoughtfully prepared breakfast that was the perfect start to our day. What truly made our experience special were the wonderful sightseeing and dinner recommendations. Amelia and Ron are phenomenal hosts who go above and beyond to ensure their guests have a memorable stay. Their genuine warmth, local knowledge, and attention to detail made our visit to Kennebunkport even more enjoyable. The Waldo Emerson is an outstanding choice for anyone looking for a charming bed and breakfast in Kennebunkport. We thoroughly enjoyed our stay and would gladly return. We highly recommend it to anyone seeking the perfect combination of comfort, charm, exceptional hospitality, and relaxation! **A truly wonderful experience from start to finish!**

Reviewed on Oct 18, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $698, price is now $588 per person
$588
per person
Jan 4 - Jan 7
found 22 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
9.6/10 Exceptional! (342 reviews)

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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
9/10 Wonderful! (1,005 reviews)
"Good stay"

Reviewed on Nov 3, 2026

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 11 to Nov 12
$89 total
Nov 11 - Nov 12
Total with taxes and fees
Clarion Hotel Portland Airport ME
See all 2,207 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 $513 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.