Portland Romantic Vacations

Book a Romantic Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top Romantic Portland Hotels

Kennebunkport Captains Collection
Kennebunkport Captains Collection
4.5 out of 5
6 Pleasant Street, Kennebunkport, ME
  • 56 min drive from Thompson's Point
Romance is in the air at this upscale hotel, featuring a garden and premium mattresses.
9.4/10 Exceptional! (501 reviews)
"The room was spacious and grande in a 19th century way. Check in was quick and painless. I was a bit put out that they ran out of coffee in the morning and that check in is not until 4pm…"

Reviewed on Jun 30, 2025

Kennebunkport Captains Collection
Breakwater Inn
Breakwater Inn
4.5 out of 5
127 Ocean Avenue, Kennebunkport, ME
  • 57 min drive from Thompson's Point
Splurge on a trip to this upscale hotel, featuring amenities like ocean-view dining and happy hours. You'll also love the premium mattresses and riverside ...
7.8/10 Good! (15 reviews)
"Had a rough start to our booking, when 2 days before arriving we were called and said our room had flooded due to a pipe burst, and they had to cancel our reservation. However, after working through Expedia the Inn found us a replacement room. Checking in was a bit confusing, as the hotel is not ..."

Reviewed on Jun 29, 2025

Breakwater Inn
The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
  • 5 min drive from Thompson's Point
If you're in the mood for love, consider staying at this romantic hotel, featuring a spa and in-room massages. You'll also love the ocean-view dining, garden, ...
8.8/10 Excellent! (1,003 reviews)

Couples like: full-service spa, couples spa treatments, restaurant with ocean view, couples dining

Travelers say...
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Reviewed on Jun 28, 2025

The Westin Portland Harborview
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.