Harpswell Vacations from $364

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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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $496, price is now $364 per person
$364
per person
Jan 5 - Jan 8
found 17 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
18.4/10 Exceptional! (1,668 reviews)
We were only here 1 night, but our room was clean and cozy. We walked right down the street for dinner at $3 Deweys and had a great time! We used our destination fee credit to have breakfast delivered and were thourouly dissapointed. I took one bite and knew something was not right, the potatoes were fried in rancid grease and inedibile. My husband had an omlet that was at least edibile but nothing special.

Reviewed on Nov 24, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $695, price is now $429 per person
$429
per person
Jan 5 - Jan 8
found 17 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
19.6/10 Exceptional! (86 reviews)
Loved this place and would definitely stay here next time we go back.

Reviewed on Oct 15, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $754, price is now $512 per person
$512
per person
Jan 5 - Jan 8
found 17 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
19.2/10 Exceptional! (161 reviews)
The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!

Reviewed on Nov 23, 2025

The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Downtown Portland
Price was $726, price is now $537 per person
$537
per person
Feb 8 - Feb 11
found 4 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
20/10 Exceptional! (2 reviews)
Really nice and clean new hotel!

Reviewed on Oct 27, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,281, price is now $955 per person
$955
per person
Jan 5 - Jan 8
found 17 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
18.8/10 Exceptional! (288 reviews)
Room was ready early friendly staff and room is better than expected

Reviewed on Nov 16, 2025

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Discover the most popular places to visit in Harpswell

Ash Cove Pottery

Enjoy an outing to Ash Cove Pottery during your stay in Harpswell. Amble around the area's seaside, or seek out its hiking trails.

Ash Cove Pottery

Harpswell Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $93 total per night from Nov 28 to Nov 29
$93 total
Nov 28 - Nov 29
Total with taxes and fees
7.8/10 Good! (1,251 reviews)
Yes we loved room 511 with the pull out bed chair !

Reviewed on Nov 19, 2025

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
$139 nightly
The price is $154 total per night from Nov 30 to Dec 1
$154 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (1,686 reviews)
We were only here 1 night, but our room was clean and cozy. We walked right down the street for dinner at $3 Deweys and had a great time! We used our destination fee credit to have breakfast delivered and were thourouly dissapointed. I took one bite and knew something was not right, the potatoes ...

Reviewed on Nov 24, 2025

Portland Harbor Hotel
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
363 Maine Mall Rd South Portland ME
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $81 total per night from Dec 2 to Dec 3
$81 total
Dec 2 - Dec 3
Total with taxes and fees
7.8/10 Good! (1,313 reviews)
The bathroom needed more cleaning. Baseboards hadn’t been dusted in a long time, looked like mold around sink and bath tub was very slippery.

Reviewed on Nov 22, 2025

DoubleTree by Hilton Hotel Portland
See all 2,089 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 $364 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.