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.
Oliver Plaza

Oliver Plaza

4 out of 5
London City Centre
per person
Jul. 19 - Jul. 26
Roundtrip flight included
Montreal (YUL) to London (LHR)
9/10 Wonderful! (827 reviews)
This is not a four star hotel. Our lower level room was so small that you can hardly open the door and walk inside at the same time. There was no room to open and store a suitcase. Don't be fooled by the pictures.

Reviewed on May 15, 2024

Baglioni Hotel London - The Leading Hotels of the World

Baglioni Hotel London - The Leading Hotels of the World

5 out of 5
London City Centre
Save 100% on your flight
per person
Jun. 21 - Jun. 25
Roundtrip non-stop flight included
Montreal (YUL) to London (LHR)
9/10 Wonderful! (348 reviews)
We stayed here for 8 days. The Baglioni is in a perfect area for exploring London while also quiet - it’s right next to Kensington Gardens/Hyde Park. The largest Whole Foods in London is 5 minutes away along with any other shop you might need on Kensington High Street. The included breakfast is a great value. The staff are excellent and helpful. Note that only suites have a park or street view - other rooms look into a courtyard which is very quiet. The spa and gym looked pretty good though we didn’t use them. Buses and underground stations are very close to get around easily. Plus several of the main museums are walking distance.

Reviewed on May 12, 2024

Tophams Hotel

Tophams Hotel

4 out of 5
London City Centre
per person
Jul. 29 - Aug. 5
Roundtrip flight included
Toronto (YYZ) to London (LHR)
8.4/10 Very Good! (365 reviews)
We purposely upgraded to the deluxe room category ( the hotel’s middle tier) and were disappointed with the quality of the room ( appointments, noisy between the floors, poor air circulation). The deluxe is more of a “ standard”. However, we were only in the room a few hours as there was an issue with the bathroom, which the hotel’s manager and night desk staff dealt with in a very professional fashion. The hotel then upgraded us to a different room ( a junior suite) which was much more in keeping with our expectations. The breakfast was good value and a good variety. The front desk staff (day staff) seemed untrained and overall unhelpful. The night staff were excellent. The hotel is very conveniently located to Victoria Station and tube, the theatre, and Buckingham palace. It is in a lovely neighborhood. Worth staying at, but upgrade to the highest level of offering.

Reviewed on May 15, 2024

Dao By Dorsett West London

Dao By Dorsett West London

4 out of 5
Hammersmith and Fulham
per person
Jul. 29 - Aug. 5
Roundtrip flight included
Toronto (YYZ) to London (LHR)
8.4/10 Very Good! (170 reviews)
Great value for money. The area has quite an urban edge with an incredible selection of places to eat. Best shopping with Westfield on the doorstep!

Reviewed on May 2, 2024

Hotel Riu Plaza London Victoria

Hotel Riu Plaza London Victoria

4 out of 5
London City Centre
per person
Jul. 5 - Jul. 12
Roundtrip flight included
Hamilton (YHM) to London (LHR)
8.6/10 Excellent! (812 reviews)
Close to the theatre (Wicked) and to Victoria station

Reviewed on May 15, 2024

Portland Beach Vacation

Whether you're traveling solo or with the family, it'll be easy to find rest and relaxation on your Portland vacation. Look for pretty seashells or sit by the water's edge and listen to the soothing sound of the surf. Whatever you decide to do, your trip to Portland is sure to be a blast. Church Ope Cove, located 2 kilometres from the city center, is a top choice for those looking for convenience. Many people also lock in Portland vacation deals closer to Portland Beach, another excellent option.

Things You Should Know About Portland

  • If fresh sea air and water views are your idea of a dreamy escape, why not think about one of our Portland beach hotels? Staying near the water is the perfect antidote to life's little stresses.
  • Cottages are another top choice for those planning a vacation in Portland. Some great options are Chesil View House and Seapinks Cottage.
  • There are plenty of activities that keep the 12,700 or so residents of Portland busy. Browsing our Portland things to do page will let you in on what this place has to offer.
  • Portland vacation deals are a superb way to save on experiences. Some ideas, such as Portland Bill Lighthouse, Portland Castle and Portland Museum, should be at the very top of your sightseeing list.

Portland Hotel Deals

Heights Hotel
Heights Hotel
3 out of 5
Yeates Road, Portland, England
The price is CA $178 per night from Jun. 2 to Jun. 3
CA $178
CA $213 total
includes taxes & fees
Jun 2 - Jun 3
8.2/10 Very Good! (510 reviews)
"Tne property is clean and the staff are very welcoming and friendly. The views from the bar are amazing."

Reviewed on May 12, 2024

Heights Hotel
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
Weymouth
10/10 Exceptional! (1 review)
Yacht "No Way"
"Had a wonderful stay on this beautiful boat, extremely clean and tidy with all the amenities you could hope for. Excellent location and lovely marina to enjoy with great facilities. Will definitely be returning again very soon. Very highly recommended."

Reviewed on Sep. 6, 2022

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Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
The Aqua
The Aqua
3 out of 5
Castletown, Portland, England
The price is CA $165 per night from May 27 to May 28
CA $165
CA $199 total
includes taxes & fees
May 27 - May 28
7.8/10 Good! (174 reviews)
"Basic hotel, Clean, welcoming, but sadly the restaurant was closed due to staff shortages. Breakfast good staff helpful. Very well located for access to the dockyard/port. Parking easy."

Reviewed on Oct. 13, 2023

The Aqua
See all 1,753 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Portland vacation package cost?
Say yes to new adventures with our Portland vacation packages, which start from only CA $1,869. Choose the flights and hotels that suit your plans. Then, add on a couple of tours or activities for a one-of-a-kind escape.
How do I get a cheap travel package to Portland?
Search for flights that fit your busy schedule, add a hotel to your booking and watch how much you save with a Portland vacation package. It’s that easy! From flights and hotels to rental cars and tours, Expedia makes traveling cheap and easy. And with over 550 partner airlines and 1,000,000 hotel options around the world to choose from, you’ll never be short of choice.
Where should I stay in Portland?
A getaway to Portland isn’t complete without seeing Chesil Beach, Portland Bill Lighthouse and Portland Harbour. Spend your evenings near these top attractions and make sightseeing simple.
What are the top hotels in Portland?
Book a stay at Boatswain’s Watch. It’s one of this neighborhood’s most popular properties. Another top option in Portland is Cove Cottage Hideaway.
How far in advance should I book my Portland vacation?
To land discount prices, book early. Air carriers typically advertise flights, along with some of the lowest fares, nearly a year prior to departure. Hotels, experiences and car rental should also be booked early so you can have the pick of the bunch. If you were hoping for a last-minute getaway to Portland, there are always lots of great deals to be had on Expedia. Check them out now!
What does an Expedia Portland travel package include?
Hotels, flights and a cool set of wheels for all your fun road trip adventures. Simply pick and choose your favorite bundle and get access to great discounts. Once you’ve made your booking, add on some experiences and tours and watch your savings stack up. When it comes to crafting your Portland getaway, you’re in charge!
What should I know before booking a Portland travel package?
Bundling your bookings into a Portland vacation package is the easiest way to organize your trip. Not only that, you’ll get great discounts when you combine your flights, hotels and car rentals. Once you’ve booked, why not add on a day tour or an activity?
Can I choose my airline with a Portland Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you certainly can. Simply pick your preferred carrier and create the perfect Portland getaway.
If I'm not able to travel, can I cancel my Portland vacation package?
Your situation can change in the blink of an eye, so yes, you can. You may be able to cancel or amend your Portland vacation package for free if you’ve booked in the last 24 hours. For older bookings, you can still make the necessary changes, but your car rental company, airline or hotel may charge a fee. Need more information? Check out our Customer Service Portal. We’re here to help make sure your trip goes off without a hitch.

Discover the most popular places to visit in Portland

Image for Portland Bill Lighthouse

Portland Bill Lighthouse

Find out about the history of Southwell when you spend time at Portland Bill Lighthouse. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

Portland Bill Lighthouse
Image for Portland Bill

Portland Bill

Commune with nature and explore the great outdoors at Portland Bill during your travels in Southwell. Stroll along the area's waterfront, or simply savor its charming coffeehouses.

Portland Bill
Image for Church Ope Cove

Church Ope Cove

Why not spend a carefree afternoon at Church Ope Cove during your travels in Southwell? Amble around the area's seaside or visit its spas.

Church Ope Cove

What to do in Portland

Image for Private 4x4 Dorset Safari. 6 Hour Cruise Ship Jeep Safari Special

Private 4x4 Dorset Safari. 6 Hour Cruise Ship Jeep Safari Special

CA $1,452
Per adult
Private 4x4 Dorset Safari. 6 Hour Cruise Ship Jeep Safari Special
Image for Half-Day Guided E-Bike Tour Portland with Brunch

Half-Day Guided E-Bike Tour Portland with Brunch

CA $221
Per adult
Half-Day Guided E-Bike Tour Portland with Brunch
Image for Pauls Walking Tour - Sundays at 10:00am - or Group book on 07851934735

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

CA $17
Per adult
Pauls Walking Tour - Sundays at 10:00am - or Group book on 07851934735
See all activities in Portland

Other vacations you might like

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