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Top Romantic vacation packages in Portland

Price found within the past 48 hours. Click for updated prices.

Kennebunkport Captains Collection

￥366,786

per person

May 20 - May 26

found 5 hours ago

Roundtrip flight included

Osaka (OSA) to Portland (PWM)

9.4/10 Exceptional! (684 reviews)

Parking is great and very convenient. Staff is very friendly. Breakfast was delicious. I do think our room could use more light. Door numbers of the rooms could be bigger. The hallway is dark making it difficult to read the numbers.

Reviewed on Mar 2, 2026

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Top Romantic Portland Hotels

Kennebunkport Captains Collection

6 Pleasant Street Kennebunkport ME

56 min drive from Thompson's Point

Premium mattresses, luxurious surroundings, and more await visiting couples at this romantic hotel.

9.4/10 Exceptional! (685 reviews)

Parking is great and very convenient. Staff is very friendly. Breakfast was delicious. I do think our room could use more light. Door numbers of the rooms could be bigger. The hallway is dark making it difficult to read the numbers.

Reviewed on Mar 2, 2026

Breakwater Inn

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 ...

8.2/10 Very Good! (52 reviews)

I’ve booked a king size and get queen size. Why I am being charged for kings while I had a queen size? The staff was rude and she gives us the explanations of her dog is dying. We made the best of it but the staff told us that she will rectify this on Monday but today is Tuesday. I am being charged ...

Reviewed on Feb 25, 2026

The Westin Portland Harborview

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! (1,004 reviews)

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

Travelers say...

The room was very clean, check in and out was easy, parking was affordable.

Reviewed on Mar 3, 2026

See all 473 properties in Portland

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.