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.
Cleveland Residences Kensington
London City Centre
Price was CA $2,411, price is now CA $1,705 per person
CA $1,705
per person
Jun 18 - Jun 24
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
8.8/10 Excellent! (237 reviews)
Kitchen well equiped. Bed very Small and not so confortable. Very well situated
Reviewed on Apr 28, 2026
Hotel Riu Plaza London Victoria
London City Centre
Price was CA $3,736, price is now CA $2,374 per person
CA $2,374
per person
Jun 20 - Jun 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to London (LHR)
9/10 Wonderful! (3,555 reviews)
Room was great with a view over the city . Very clean and had simple things like a mirror above the desk to do make up etc . Breakfast was lovely , staff were really helpful . Great location across from Victoria station
Reviewed on Apr 28, 2026
The Savoy
London City Centre
Price was CA $7,516, price is now CA $5,218 per person
CA $5,218
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to London (LHR)
9.6/10 Exceptional! (1,001 reviews)
Attention to detail and high levels of service made this a stay to remember! Took excellent care of me and my family all week-cannot recommend enough! If Expedia had a 10 star system, I’d give them an 11!
Reviewed on Apr 18, 2026
1 Hotel Mayfair
London City Centre
Price was CA $6,638, price is now CA $4,659 per person
CA $4,659
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to London (LHR)
9.6/10 Exceptional! (388 reviews)
Stunning hotel. Rooms are spacious. Staff is top notch. Bar is a blast on the weekend!
Reviewed on Apr 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.
Portland Hotel Deals
Heights Hotel
Yeates Road Portland England
The price is CA $229 per night from May 17 to May 18
CA $229
CA $274 total
May 17 - May 18
includes taxes & fees
8.4/10 Very Good! (693 reviews)
The view from the hotel is spectacular. Inside the room and corridors the decor is dated and shabby. The bathroom taps were grubby with grime and difficult to turn. No bottled water in the room and next to no soundproofing between rooms, especially bathrooms. The fire doors in the corridor banged ...
Reviewed on Apr 26, 2026
The Aqua
Castletown Portland England
The price is CA $195 per night from May 6 to May 7
CA $195
CA $234 total
May 6 - May 7
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
One bed apartment next to Chesil Beach Dorset
Portland England
9.6/10 Exceptional! (12 reviews)
A nice spot opposite the beach, very convenient for the port. Plenty of parking around the apartment.
Reviewed on Apr 28, 2026
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
Half-Day Guided E-Bike Tour Portland with Brunch
CA $240
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
