Harpswell Vacations from $453

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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.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $664, price is now $453 per person
$453
per person
May 18 - May 22
found 8 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The room was very clean!

Reviewed on Oct 31, 2025

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,523, price is now $1,072 per person
$1,072
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (273 reviews)
Check-in and check-out are a breeze, easy access to a city parking lot on the block (needed as there was a snow ban on parking when I visited!). In terms of the space itself - clean, well appointed, spacious. Honestly a treat to stay here!

Reviewed on Feb 23, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,255, price is now $897 per person
$897
per person
May 21 - May 25
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (1,765 reviews)
Business facilities were perfect. Front desk man Roman was an all star helping us out. Whole stay was 100/100

Reviewed on Mar 4, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,550, price is now $1,161 per person
$1,161
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,005 reviews)
Great hotel with super nice views!

Reviewed on Mar 1, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $790, price is now $603 per person
$603
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The whole was cozy! Well curated style and knowledgeable staff.

Reviewed on Jan 5, 2026

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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

1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage

Harpswell ME
9.6/10 Exceptional! (172 reviews)
Excellent communication, clean property. Exactly what we expected

Reviewed on Jan 19, 2026

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1 room luxury ocean front studio cottage
Beautiful Oceanfront House- Stunning Water Views

Beautiful Oceanfront House- Stunning Water Views

Harpswell ME
9.4/10 Exceptional! (23 reviews)
A great house to stay, with incredible views and blessed peace and quiet. I would recommend this place to everyone.

Reviewed on Nov 12, 2025

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Beautiful Oceanfront House- Stunning Water Views
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $108 total per night from Mar 22 to Mar 23
$108 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
The room was very clean, check in and out was easy, parking was affordable.

Reviewed on Mar 3, 2026

The Westin Portland Harborview
See all 2,098 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 $453 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.