Portland Vacation Packages

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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.
Montcalm Mayfair Townhouse

Montcalm Mayfair Townhouse

4 out of 5
London City Centre
Price was CA $2,897, price is now CA $1,983 per person
CA $1,983
per person
Aug 4 - Aug 10
found 5 hours ago
Roundtrip flight included
Montreal (YMQ) to London (LHR)
8/10 Very good! (20 reviews)

Apartment in Pimlico Near Tate Britain

Apartment in Pimlico Near Tate Britain

2 out of 5
London City Centre
Price was CA $6,781, price is now CA $3,917 per person
CA $3,917
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to London (LHR)
No reviews

Stylish Duplex Apartment in Fulham

Stylish Duplex Apartment in Fulham

2.5 out of 5
Hammersmith and Fulham
Price was CA $3,719, price is now CA $2,473 per person
CA $2,473
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to London (LHR)
No reviews

Hotel Riu Plaza London Victoria

Hotel Riu Plaza London Victoria

4 out of 5
London City Centre
Price was CA $3,010, price is now CA $2,040 per person
CA $2,040
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to London (LHR)
9/10 Wonderful! (3,822 reviews)
Great room, amazing AC, best hotel breakfast I’ve had in a long time, big buffet, right next to Victoria station so public transit everywhere was so easy.

Reviewed on Jun 30, 2026

Leicester House Hotel

Leicester House Hotel

3 out of 5
London City Centre
Price was CA $3,320, price is now CA $2,285 per person
CA $2,285
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to London (LHR)
8.8/10 Excellent! (70 reviews)
Front desk was amazing! I have some mobility issues, and was assisted to the room, always asked upon daily arrival or exit if there was AMYTHING they could help with, and had our taxi to the airport ready 20 minutes before scheduled. 5 star in my book!

Reviewed on Jun 26, 2026

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 $233 per night from Jul 5 to Jul 6
CA $233
CA $280 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very good! (708 reviews)
"Excellent location for amazing views of Chesil Beach & wonderful very friendly and efficient staff."

Reviewed on Jun 22, 2026

Heights Hotel
The Aqua

The Aqua

3 out of 5
Castletown Portland England
The price is CA $196 per night from Jul 28 to Jul 29
CA $196
CA $235 total
Jul 28 - Jul 29
includes taxes & fees
The Aqua
Fairhaven Hotel

Fairhaven Hotel

3 out of 5
Fairhaven Hotel, 37 Esplanade Weymouth England
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Jul 5 to Jul 6
CA $127
CA $153 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very good! (814 reviews)
"It was clean and a enjoyable stay"

Reviewed on Jun 30, 2026

Fairhaven Hotel
See all 1,996 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Portland attractions

A coastal landscape with a prominent red and white lighthouse, rocky cliffs, and a white building with a green roof.

Portland Bill Lighthouse

9.2/10 (189 reviews)
Find out about the history of Portland when you spend time at Portland Bill Lighthouse. Wander the area's beautiful beaches or simply enjoy one of its charming coffeehouses.
See properties

What to do in Portland

Pauls Walking Tour - Sundays at 10:00am - or Group

Pauls Walking Tours - Sundays at 10:00am

CA $19
per adult
Pauls Walking Tours - Sundays at 10:00am
Half-Day Guided E-Bike Tour Portland with Lunch

Half-Day Guided E-Bike Tour Portland with Brunch

CA $240
per adult
Half-Day Guided E-Bike Tour Portland with Brunch
Nordic Walking Tour of Weymouths Iconic Landmarks

Nordic Walking Tour of Weymouth’s Iconic Landmarks

CA $17
per adult
Nordic Walking Tour of Weymouth’s Iconic Landmarks
See all activities in Portland

Frequently asked questions

How much does a Portland vacation package cost?
You'll find cheap prices from CA $1,983 on Expedia for your Portland break. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Portland costs.
What are the cheapest months to go to Portland?
Travel in the shoulder or low season and you're likely to score cheap Portland vacation packages. Bear in mind that school vacation periods and major events and festivals can have an impact on prices, so do a little research before booking.
How many days is enough for Portland?
With a well-planned schedule, you can easily hit the main Portland attractions in a few days. But if you want to discover lesser-known spots or go on day tours, think about booking your Portland vacation for longer.
Is it worth booking a vacation package to Portland?
Portland has everything you need for the perfect getaway — walking trails, camping and watersports are just the start. Whether you want to check out sights like Weymouth and Portland National Sailing Academy and Portland Castle, or take the road less travelled, you'll have plenty to experience on your Portland vacation.
How to find the best Portland package deals?
Begin your search for a Portland package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Portland package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Portland getaway off to a flying start.
Is it cheaper to book a Portland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Portland vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Portland?
Land fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Portland trip.
How to plan a trip to Portland?

  1. Choose your travel dates: What you want to do in Portland and your preferred season will help you decide when to go.
  2. Plan your budget wisely: On top of the cost of your accommodations, you'll need to consider other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that may come up during your trip to Portland.
  3. Decide how long to go away for: Now that you're more familiar with Portland, you can figure out the perfect length of your break. Pull together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Combine your airfare and accommodations: After you've settled on your travel dates and duration, book the ideal Portland vacation package for you.

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.