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.
Three Falcons Hotel

Three Falcons Hotel

4 out of 5
City of Westminster
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
8.8/10 Excellent! (320 reviews)
Room was recently renovated and comfortable but a proper chair would have been appreciated. The fact that there was no space for a small desk and chair will give you a sense of the small size of the room.

Reviewed on Jul. 21, 2025

The Savoy

The Savoy

5 out of 5
London City Centre
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to London (LHR)
9.6/10 Exceptional! (1,001 reviews)
The location was perfect for my needs, and I appreciated the hospitality. I’d definitely recommend this place to others and would stay again in the future.

Reviewed on Jul. 7, 2025

Leicester Square Studios

Leicester Square Studios

2 out of 5
London City Centre
per person
Sep 15 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
9/10 Wonderful! (28 reviews)
Great location! Nice little apartment in a bustling area. Highly recommend

Reviewed on May 8, 2025

1 Hotel Mayfair

1 Hotel Mayfair

5 out of 5
London City Centre
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to London (LHR)
9.6/10 Exceptional! (267 reviews)
We loved our stay at the 1 Hotel Mayfair! The property was beautiful and extremely elevated, and the service was truly wonderful.

Reviewed on Jul. 11, 2025

Collingham Road - 2 Bedroom Apartment I

Collingham Road - 2 Bedroom Apartment I

2 out of 5
London City Centre
per person
Sep 15 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
No reviews

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 $200 per night from Jul 27 to Jul 28
CA $200
CA $240 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (658 reviews)
"The view from the restaurant is spectcular. Food is good, rooms need a make over"

Reviewed on Jul. 17, 2025

Heights Hotel
The Aqua

The Aqua

3 out of 5
Castletown, Portland, England
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Aug 18 to Aug 19
CA $191
CA $230 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (188 reviews)
"Good location for Portland Harbour watersports and good value for money given a full breakfast was included in the price"

Reviewed on Jun. 14, 2025

The Aqua
Fairhaven Hotel

Fairhaven Hotel

2.5 out of 5
Fairhaven Hotel, 37 Esplanade, Weymouth, England
The price is CA $114 per night from Jul 27 to Jul 28
CA $114
CA $137 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (621 reviews)
"English staff on reception. Location was close to amenities. Internal door closures were adjusted so that doors did not bang shut."

Reviewed on Jul. 16, 2025

Fairhaven Hotel
See all 1,811 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

What to do in Portland

Pauls Walking Tour - Sat & Sundays at 10:00am - or Group book on 07851934735

Pauls Walking Tour - Sundays at 10:00am - or Group book on 07851934735

CA $19
per adult
Pauls Walking Tour - Sundays at 10:00am - or Group book on 07851934735
See all activities in Portland

Frequently asked questions

How much does a Portland vacation package cost?
You'll find cheap prices from CA $1,569 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.

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