Portland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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

    Plan, book, and manage your trip all in one place

Your Portland Vacation

Prepare to experience Portland on your own terms with a custom Portland vacation package! Uncovering the treasures of this interesting city is made easier with a base in a neighborhood such as Winfrith Newburgh, which is great for nature, among lots of other things. A trip to Portland is a terrific opportunity to see the sights. Be sure to look around well-known attractions like Weymouth Beach, Chesil Beach and Weymouth Harbour. Stop daydreaming and start adventuring. Check out the wide range of options on Expedia today and finally put your Portland vacation plans into action!

Top Portland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Argo Hotel - Kings Cross
Apartment in Pimlico Near Tate Britain
Hotel Riu Plaza London Victoria
Characterful Cottage With hot Tub, No Deposit
Hotel Riu Plaza London The Westminster

Portland Beach Vacation

Get set to live out those beachy daydreams on your Portland vacation. Embark on a romantic stroll, soak up the spectacular coastal views and pick up pretty seashells on your trip to Portland. Only 0.97 kilometres from the centre of town, Church Ope Cove is the place to be for many travellers. Browse our Portland vacation packages and watch your travel budget stretch further!

Things You Should Know About Portland

  • Check into one of our Portland beach hotels and experience this destination at its very best. Wander along the shoreline and marvel in the gorgeous sunsets right on your front door.
  • Our cottages, like Heights Hotel and The Aqua, are popular with visitors of all types. Check out the amenities and get ready for your vacation in Portland!
  • Some 12,700 people live in Portland. If you want recommendations about what to see and do around these parts, why not ask a couple of the friendly locals? Our Portland things to do page is also a handy source of information.
  • Don't leave town without checking out Portland Harbour, Portland Bill and Weymouth and Portland National Sailing Academy. With the money you save through our Portland vacation deals, you can see more top sights like these.

Ready to book your vacation to Portland?

 

Choose your dates

Portland Hotel Deals

Heights Hotel

Heights Hotel

3 out of 5
Yeates Road Portland England
The price is CA $218 per night from Apr 13 to Apr 14
CA $218
CA $261 total
Apr 13 - Apr 14
includes taxes & fees
8.4/10 Very Good! (689 reviews)
Great stay, views from the bar/restaurant are amazing. Outside the buildings looks a little dated (partly because of the salt/weather exposure) but felt modernised inside.

Reviewed on Mar 31, 2026

Heights Hotel
The Aqua

The Aqua

3 out of 5
Castletown Portland England
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Apr 20 to Apr 21
CA $187
CA $225 total
Apr 20 - Apr 21
includes taxes & fees
8/10 Very Good! (194 reviews)
I was attending a course in the leisure centre next door. The Aqua was an excellent, relaxed place to stay. The staff/owners were polite, friendly and generated a relaxed atmosphere. The small, well stocked bar carried on this relaxing, informal atmosphere. (The squeaky bar stools could do with fixing ...

Reviewed on Oct 20, 2025

The Aqua
One bed apartment next to Chesil Beach Dorset

One bed apartment next to Chesil Beach Dorset

Portland England
9.4/10 Exceptional! (10 reviews)
Pet friendly very clean amazing location pubs and places to eat walking distance highly recommend it

Reviewed on Mar 30, 2026

One bed apartment next to Chesil Beach Dorset
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.

What to do in Portland

Explore a world of travel with Expedia

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