Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Portland

Heights Hotel

Heights Hotel

3 out of 5
Yeates Road Portland England
The price is 4.364.377 ₫ per night from 19 Jul to 20 Jul
4.364.377 ₫
5.237.253 ₫ total
19 Jul - 20 Jul
includes taxes & fees
8.4/10 Very good! (710 reviews)
"We've rarely felt less welcome. Desk staff were surly and seemed to resent our intrusion into their day by, you know, checking in. The breakfast staff next morning were also surly, though the woman serving in the Café in the evening was cheery and pleasant. The advertised EV charging is a myth. There's ..."

Reviewed on 9 Jul 2026

Heights Hotel
The Aqua

The Aqua

3 out of 5
Castletown Portland England
Fully refundableReserve now, pay when you stay
The price is 3.726.107 ₫ per night from 13 Jul to 14 Jul
3.726.107 ₫
4.471.469 ₫ total
13 Jul - 14 Jul
includes taxes & fees
The Aqua
Fairhaven Hotel

Fairhaven Hotel

3 out of 5
Fairhaven Hotel, 37 Esplanade Weymouth England
Fully refundableReserve now, pay when you stay
The price is 2.931.101 ₫ per night from 19 Jul to 20 Jul
2.931.101 ₫
3.517.321 ₫ total
19 Jul - 20 Jul
includes taxes & fees
8.4/10 Very good! (824 reviews)
"It was clean staff great had a lovely time"

Reviewed on 7 Jul 2026

Fairhaven Hotel
See all 1,993 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 top-notch restaurants.
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Frequently asked questions

How much does a Portland holiday package cost?
You'll find cheap prices 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 holiday 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 holiday 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-organised 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 holiday for longer.
Is it worth booking a holiday package to Portland?
Popular for its walking trails, camping and watersports, a Portland holiday 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 customise 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 holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking flights and accommodation individually. Better still, you can personalise 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 holiday 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 holiday.
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 accommodation: Once you've nailed down your trip dates and duration, book the ideal Portland holiday package for you.

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