Harpswell Vacations from $817

Book a Hotel + Flight or Car together to unlock savings

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
Price was $1,173, price is now $817 per person
$817
per person
Jun 23 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Greenville (GSP) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The room was very clean!

Reviewed on Oct 31, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,577, price is now $1,090 per person
$1,090
per person
May 23 - May 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
The property is amazing and the staff were polite and very attentive. It’s a negative for me that I couldn’t take my 8 year old in the outdoor pool, but I’m sure if i wasn’t there with a child I’d appreciate a kid-free zone. The indoor pool was pretty filthy, with some wrappers and things floating in the water. The room service food was surprisingly just okay, with watery omelettes, minimalist potatoes for breakfast, a namesake pork sandwich that leaned toward a Cuban but took a left hand toward a crockpot pork. The chefs plate charcuterie was fine except for some form of pate that appeared as if the chef had chewed up some prosciutto , formed it into a rectangle, and pressed two pistachio bits it. I figured it for a nasty kitchen prank on the wealthy snobs paying $35 for a lunch able, so I left it behind. I can’t lie — the whole milk from a local farm that was supplied on each floor’s coffee bar was the best milk I’ve ever tasted in my life. I literally skipped the coffee and drank the milk by the glass, this cannot be overstated as trivial as it seems.

Reviewed on Mar 31, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $1,134, price is now $841 per person
$841
per person
May 15 - May 18
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (178 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!

Reviewed on Mar 10, 2026

Grasshopper Inn

Grasshopper Inn

4 out of 5
Save 100% on your flight
Price was $1,523, price is now $1,160 per person
$1,160
per person
May 26 - May 30
found 1 day ago
Roundtrip non-stop flight included
Greenville (GSP) to Portland (PWM)
9.8/10 Exceptional! (71 reviews)
We had a fantastic stay at Grasshopper Inn and will definitely return when back in the area. Clean, friendly staff and brilliant location.

Reviewed on Oct 22, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,755, price is now $1,392 per person
$1,392
per person
Jun 23 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Greenville (GSP) to Portland (PWM)
9.2/10 Wonderful! (1,766 reviews)
I would definitely recommend the Portland Harbor Hotel. The location was perfect for visiting the Old Port area; one block up from the waterfront. The hotel was quiet. The rooms were well appointed (we had a courtyard view junior suite. The staff was very friendly and a pleasure to speak with. The restaurant had a very nice breakfast menu as well as a dinner menu.

Reviewed on Apr 10, 2026

Don't see what you're looking for?
See all available trips from Columbus to Harpswell
View all trips

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

Get rates
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

Get rates
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
$114 nightly
The price is $126 total per night from Apr 26 to Apr 27
$126 total
Apr 26 - Apr 27
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
I chose this hotel specifically because it was advertised as pet-friendly, as I was traveling with my well-trained dog. While the location was convenient and the room itself was comfortable, the experience was soured by the lack of transparency regarding the pet policy. When I booked, the additional ...

Reviewed on Apr 6, 2026

The Westin Portland Harborview
See all 2,119 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Harpswell vacation package cost?
You'll find cheap prices from $817 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.