Weymouth and Portland District Romantic Vacations

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

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How to find a romantic Weymouth and Portland District vacation

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

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Weymouth and Portland District romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Weymouth and Portland District?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Weymouth and Portland District?

Put a price on love with stunning deals for duos starting at just . Prices and availability are subject to change. Additional terms may apply.

Can I book Weymouth and Portland District spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Weymouth and Portland District?

To book a loved-up break in Weymouth and Portland District, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

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

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Weymouth and Portland District romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?

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 Chesil Beach are located ...
9.4/10 Exceptional! (107 reviews)
Very nice
"Great hotel. You can tell they are making the extra effort. Nice breakfast."

Reviewed on Aug 5, 2025

The George B&B
The Cumberland

The Cumberland

3 out of 5
95 The Esplanade, Weymouth, England
  • 6 min walk from Weymouth Beach
Whatever your love language might be, you and your special someone are sure to love the waterfront location at this romantic hotel.
9.4/10 Exceptional! (737 reviews)
Great seafront hotel, best location
"I had a lovely stay at the Cumberland Hotel. Mike, the owner, was incredibly friendly and welcoming, which made the experience even more enjoyable. The attention to detail throughout the hotel was impressive—everything was thoughtfully arranged, from the plentiful extra towels to the little surprises ..."

Reviewed on Aug 4, 2025

The Cumberland
Heights Hotel

Heights Hotel

3 out of 5
Yeates Road, Portland, England
  • 9 min drive from Weymouth Beach
If you're in the mood for love, consider staying at this romantic hotel, featuring ocean-view dining and a garden. You'll also love the champagne service, terrace, ...
8.2/10 Very Good! (662 reviews)

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

Travelers say...
"Gorgeous view of Lyme Bay. The perfect end point for this leg of our SW Coastal hike."

Reviewed on Jul 24, 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.

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