Portland Romantic Holidays

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

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages with flights are ATOL protected

How to find a romantic Portland holiday

How can I find the best Portland vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Portland. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Portland romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Portland that start from . Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Portland romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Portland?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Portland?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Portland that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Portland with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Portland romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

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
Stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
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 2 Mar 2026

Kennebunkport Captains Collection
Breakwater Inn

Breakwater Inn

4.5 out of 5
127 Ocean Avenue Kennebunkport ME
  • 57 min drive from Thompson's Point
Stay at this luxury hotel in Kennebunkport. Enjoy free Wi-Fi, free parking and free bicycles on-site. Our guests praise the helpful staff in their reviews. Popular ...
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 25 Feb 2026

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
Stay at this spa hotel in Portland. Enjoy free Wi-Fi, a full-service spa and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,004 reviews)

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

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

Reviewed on 3 Mar 2026

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.

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.