Weymouth and Portland District Romantic Holidays

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

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How to find a romantic Weymouth and Portland District holiday

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

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Weymouth and Portland District. 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 Weymouth and Portland District 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 Weymouth and Portland District that start from . Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Weymouth and Portland District 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 Weymouth and Portland District?

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 Weymouth and Portland District?

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 Weymouth and Portland District 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 Weymouth and Portland District 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 Weymouth and Portland District 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 Weymouth and Portland District Hotels

The George B&B
The George B&B
3 out of 5
65 Dorchester Road, Weymouth, England
  • 16 min walk from Weymouth Beach
Stay at this 3-star B&B in Weymouth. Enjoy free breakfast, free parking and daily housekeeping. Popular attractions Weymouth Beach and Weymouth Harbour are located ...
9.4/10 Exceptional! (100 reviews)
"My room was very roomy and comfortable, the breakfast was fresh and very nice, highly recommended."

Reviewed on 2 Jul 2025

The George B&B
The Cumberland
The Cumberland
3 out of 5
95 The Esplanade, Weymouth, England
  • 6 min walk from Weymouth Beach
Stay at this 3-star beach hotel in Weymouth. Enjoy free breakfast, free Wi-Fi and daily housekeeping. Our guests praise the breakfast and the helpful staff in ...
9.4/10 Exceptional! (729 reviews)
"Late booking and glad I could find such a lovely room with a sea view. Fantastic service and lovely breakfast."

Reviewed on 29 Jun 2025

The Cumberland
Heights Hotel
Heights Hotel
3 out of 5
Yeates Road, Portland, England
  • 9 min drive from Weymouth Beach
Stay at this 3-star hotel in Portland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
8.2/10 Very Good! (657 reviews)

Couples like: restaurant with ocean view, couples dining, champagne service

Travellers say...
"Fabulous position. Views amazing. Some of the friendliest and happiest staff we've come across. The rooms and dining area were spotless. Very impressed"

Reviewed on 27 Jun 2025

Heights Hotel
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.