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.
Residence Inn by Marriott London Kensington

Residence Inn by Marriott London Kensington

London City Centre
Save 100% on your flight
CA $1,786
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to London (LHR)
8.6/10 Excellent! (1,360 reviews)
Corinthia London

Corinthia London

London City Centre
Save 100% on your flight
CA $6,008
per person
Nov 20 - Nov 26
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
9.8/10 Exceptional! (1,002 reviews)
Park Lane Apartments Crawford Place

Park Lane Apartments Crawford Place

London City Centre
Save 100% on your flight
CA $8,986
per person
Dec 3 - Dec 6
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
8/10 Very good! (24 reviews)
Really great apartment and would stay there again on my next trip. Location is wonderful and apartment is spacious and sunny

Reviewed on Oct 1, 2026

Residence Inn by Marriott London Bridge

Residence Inn by Marriott London Bridge

London City Centre
CA $2,687
per person
Dec 25 - Dec 31
found 8 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to London (LHR)
9/10 Wonderful! (791 reviews)
I spent 26 days here. It was good value and very convenient location. The staff were nice. Unfortunately, I had my backpack with my work laptop stolen from the breakfast space. I was away from the table for less than 4 minutes. cctv shows the man walking in the lobby, walking through the restaurant, picking up my bag and walking out. while I was there someone else had their mobile phone taken out of their hand while standing in front of the hotel. This unfortunately is common in London. I was not happy with the security (and told the front desk). Anyone can get to a guest floor. You don’t need your room key to get into the ground floor stairwell or through the doors on guest floors. And there is no security downstairs.while the front desk is immediately in front of the doors, many times they are not watching and often I walked in without anyone seeing me. Housekeeping wasn’t the greatest. As this had a kitchen they provide you with a kitchen towel (same as a bath and hand towel for the bathroom). When the kitchen towel needed replacing I put it on the floor, they put it back on the counter. The next time I put it with more towels. They took it and didn’t replace. I also came home to the rubbish bin perched on my line of shoes which I had along the wall. I use my own silk pillowcase to sleep on, every time they made the bed (I didn’t choose housekeeping every day) they put that pillowcase (the obvious one I use) behind. All this to say it was convenient.

Reviewed on Oct 4, 2026

Residence Inn by Marriott London Tower Bridge

Residence Inn by Marriott London Tower Bridge

London City Centre
CA $2,664
per person
Dec 18 - Dec 24
found 21 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to London (LHR)
8.6/10 Excellent! (1,000 reviews)
Great location and very quiet

Reviewed on Sep 23, 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

Yeates Road Portland England
CA $180
CA $216 total
Nov 8 - Nov 9
includes taxes & fees
8.4/10 Very good! (728 reviews)
"Very friendly and welcoming staff on arrival. Nice Reception area, but once you get beyond the reception the corridors and our room (203) were somewhat austere. Nice breakfast, but a wider selection of fresh fruit salad would be very welcome. The red berries were still frozen but the cooked breakfast ..."

Reviewed on Oct 11, 2026

Heights Hotel
Coastal bungalow retreat on the Jurassic Coast at Portland, Dorset.

Coastal bungalow retreat on the Jurassic Coast at Portland, Dorset.

Portland Dorset
Coastal bungalow retreat on the Jurassic Coast at Portland, Dorset.
 Beautiful, family friendly Cottage with sea views of Chesil Beach

Beautiful, family friendly Cottage with sea views of Chesil Beach

Fortuneswell ENG
9.2/10 Wonderful! (34 reviews)
"All good and nice spot. Parking is sometimes a bit challenging but manageable. A dishwasher would had been better than a washing machine in the kitchen but obviously that depends on personal preferences.The ice machine was great to have."

Reviewed on Sep 8, 2026

Get rates
Beautiful, family friendly Cottage with sea views of Chesil Beach
See all 2,179 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.

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 lively bars.
See properties
A rocky coastline with waves crashing against the rocks.
Photo by Dan Weston

Portland Bill

9.0/10 (88 reviews)
Commune with nature and explore the great outdoors at Portland Bill during your travels in Portland. Stroll along the area's beautiful beaches, or simply savor its charming coffeehouses.
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A rocky beach with waves crashing onto the shore and a cliff in the background.
Photo by Kye Carter

Church Ope Cove

8.4/10 (32 reviews)
Why not spend a carefree afternoon at Church Ope Cove during your travels in Portland? While you're here, you can savor the top-notch restaurants.
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Portland Harbour

9.0/10 (10 reviews)
Explore the waterfront in Portland with a trip to Portland Harbour. Stroll along the area's waterfront, or simply savor its lively bars.
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Weymouth and Portland National Sailing Academy

9.2/10 (5 reviews)
Enjoy the collegiate vibe when you visit Weymouth and Portland National Sailing Academy, during your travels in Portland. Wander the area's beautiful beaches or simply enjoy one of its lively bars.
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Portland Castle

8.4/10 (7 reviews)
Portland Castle is just one of the places to see in Portland, so why not enjoy the other things to explore during your travels? Wander the area's beautiful beaches or simply enjoy one of its lively bars.
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The Olympic Rings Stone Sculpture

7.4/10 (6 reviews)
You can find out about the history of Portland with a visit to The Olympic Rings Stone Sculpture. While you're here, you can savor the top-notch restaurants.
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Verne High Angle Battery

8.6/10 (7 reviews)
You can learn about the history of Portland with a visit to Verne High Angle Battery. Stroll along the area's seaside, or simply savor its lively bars.
See properties

What to do in Portland

SEA LIFE Weymouth

SEA LIFE Weymouth

CA $32
per adult
SEA LIFE Weymouth
Portland Jurassic Coast Guided Mini Bus Excursions

JURASSIC COAST ADVENTURE - Guided Mini Bus Excursion-Small Groups

CA $298
per adult
JURASSIC COAST ADVENTURE - Guided Mini Bus Excursion-Small Groups
Half-Day Guided E-Bike Tour Portland with Brunch

Guided E-Bike Tour of the Isle of Portland, Dorset

CA $242
per adult
Guided E-Bike Tour of the Isle of Portland, Dorset
See all activities in Portland

Frequently asked questions

How much does a Portland vacation package cost?
You'll find cheap prices from CA $1,786 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.