Portland Vacations from ￥254,852

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Portland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Leicester House Hotel

Leicester House Hotel

3 out of 5
London City Centre
per person
Sep 4 - Sep 9
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to London (LHR)
8.4/10 Very Good! (31 reviews)
Quiet, clean, and modern. Excellent location for going anywhere.

Reviewed on Aug 3, 2025

The Savoy

The Savoy

5 out of 5
London City Centre
Save 100% on your flight
per person
Sep 10 - Sep 15
found 15 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to London (LHR)
9.6/10 Exceptional! (1,001 reviews)
The property itself is nice but the rooms are not; the junior suite I stayed in was dingy with no view which made it feel dark, dreary and dilapidated.

Reviewed on Jul 31, 2025

1 Hotel Mayfair

1 Hotel Mayfair

5 out of 5
London City Centre
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) 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

Mayfair Darley House by Viridian Apartments

Mayfair Darley House by Viridian Apartments

4 out of 5
London City Centre
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to London (LHR)
10/10 Exceptional! (3 reviews)
An absolutely fabulous place to stay, we loved it. So much so we are returning today to stay again. Robert the guest service/concierge manager is so lovely. The apartment truly is everything you need for a home from home experience staying central to everything around. Absolutely recommend!

Reviewed on Feb 5, 2025

Mowbray Court Hotel

Mowbray Court Hotel

3.5 out of 5
London City Centre
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to London (LHR)
7.8/10 Good! (1,007 reviews)
The manager gave me a complimentary breakfast on my last morning and on my first morning I was able to go to my room as soon as I checked in - at 8 a.m.!

Reviewed on Jul 29, 2025

Find the Best Portland Vacation Packages

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 kilometers from the center of town, Church Ope Cove is the place to be for many travelers. 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

Heights Hotel

3 out of 5
Yeates Road, Portland, England
8.2/10 Very Good! (661 reviews)
"Gorgeous view of Lyme Bay. The perfect end point for this leg of our SW Coastal hike."

Reviewed on Jul 24, 2025

Get rates
Heights Hotel
Fairhaven Hotel

Fairhaven Hotel

2.5 out of 5
Fairhaven Hotel, 37 Esplanade, Weymouth, England
Fully refundableReserve now, pay when you stay
The price is ￥13,665 per night from Aug 4 to Aug 5
￥13,665
￥16,398 total
Aug 4 - Aug 5
includes taxes & fees
8.4/10 Very Good! (634 reviews)
"The staff were friendly and helpful. They have food and a selection of alcoholic, non alcoholic and te and coffee. The food is amazing, my favourite was the truffle and parmesan cheese chips."

Reviewed on Jul 29, 2025

Fairhaven Hotel
Best Western Weymouth Hotel Rembrandt

Best Western Weymouth Hotel Rembrandt

3 out of 5
12-18 Dorchester Road, Weymouth, England
Fully refundableReserve now, pay when you stay
The price is ￥19,819 per night from Aug 17 to Aug 18
￥19,819
￥23,783 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Brilliant stay, the staff were all so friendly and helpful. Great location. Lovely sized room, comfortable, large bed"

Reviewed on Jul 28, 2025

Best Western Weymouth Hotel Rembrandt
See all 1,846 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.

Discover the most popular places to visit in Portland

Portland Bill Lighthouse is a functioning lighthouse at Portland Bill, on the Isle of Portland, Dorset, England. One of the many beautiful places to see around the Jurassic Coast, down south in England. #jurassicCoast #PortlandBill #lighthouse #trulyBritish

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 charming coffeehouses.

Portland Bill Lighthouse

What to do in Portland

Portland Shore Excursion to Jurassic Coast Highlights

Portland Shore Excursion to Jurassic Coast Highlights

￥14,539
per adult
Portland Shore Excursion to Jurassic Coast Highlights
See all activities in Portland

Frequently asked questions

How much does a Portland vacation package cost?
You'll find cheap prices from ￥254,852 on Expedia for your Portland escape. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Portland costs.
What are the cheapest months to go to Portland?
Plan your trip for the low season and you're likely to score cheap Portland vacation packages. Keep in mind that public holidays and local festivals and events can impact prices, so do a little research before you go.
How many days is enough for Portland?
With a well-organized itinerary, you can easily tick off the top Portland sights in a few days. But if you'd like to discover hidden spots or go on day trips, think about booking your Portland vacation for longer.
Is it worth booking a vacation package to Portland?
Popular for its walking trails, camping and watersports, a Portland vacation is a hit with all kinds of visitors. Be sure to visit major sights like Weymouth and Portland National Sailing Academy and Portland Castle, and consider renting some wheels for day trips to discover even more.
How to find the best Portland package deals?
Landing a cheap Portland package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Portland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Portland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations individually. Better still, you can personalize your Portland getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Portland?
Secure incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Portland vacation.
How to plan a trip to Portland?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Portland.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Portland. Then, pick a property that fits your budget, whether that's an economical stay or a lavish retreat.
  3. Decide how many days away: Start by compiling a list of the activities and sights you want to experience in Portland. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your airfare and accommodations: Once you've nailed down your trip 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.