Portland Vacations from $812

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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!

The Latest Portland vacation packages

Price found within the past 48 hours. Click for updated prices.
The Hanbury Townhouse

The Hanbury Townhouse

3 out of 5
Islington
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to London (LHR)
9.4/10 Exceptional! (46 reviews)
Very charming small hotel

Reviewed on Jun 25, 2025

Grange Portland

Grange Portland

4 out of 5
London City Centre
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to London (LHR)
8.2/10 Very Good! (270 reviews)
Hotel was very nice with very large rooms. Everything was good, rooms just need alttle TLC and refreshing. Hotel close to a few Underground Stations and basically around the corner to the British Museum.

Reviewed on Jun 10, 2025

Leicester Square Studios

Leicester Square Studios

2 out of 5
London City Centre
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to London (LHR)
9.2/10 Wonderful! (24 reviews)
Great location! Nice little apartment in a bustling area. Highly recommend

Reviewed on May 8, 2025

Kings Cross- 2 Bedroom Apartment

Kings Cross- 2 Bedroom Apartment

2 out of 5
London City Centre
Save 100% on your flight
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to London (LHR)
No reviews
The Zetter Clerkenwell

The Zetter Clerkenwell

4 out of 5
London City Centre
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to London (LHR)
9.2/10 Wonderful! (138 reviews)
Nice old moldings and paneling, cozy lobby with plush old chairs, very friendly, helpful staff

Reviewed on Jun 29, 2025

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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

5/5(4 reviews)

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
Beautiful quiet beach Very big pebbles, rocks so probably don't attempt to go barefoot.

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

Portland Harbour

Explore the waterfront in Portland with a trip to Portland Harbour. Stroll along the area's seaside, or simply savor its lively bars.

Portland Harbour

What to do in Portland

Portland Shore Excursion to Jurassic Coast Highlights

Portland Shore Excursion to Jurassic Coast Highlights

$107
per adult
Portland Shore Excursion to Jurassic Coast Highlights
Half-Day Guided E-Bike Tour Portland with Brunch

Half-Day Guided E-Bike Tour Portland with Brunch

$174
per adult
Half-Day Guided E-Bike Tour Portland with Brunch
Pauls Walking Tour - Sat & Sundays at 10:00am - or Group book on 07851934735

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

$13
per adult
Pauls Walking Tour - Sundays at 10:00am - or Group book on 07851934735
See all activities in Portland

Portland Hotel Deals

Heights Hotel
Heights Hotel
3 out of 5
Yeates Road, Portland, England
8.4/10 Very Good! (656 reviews)
"Fabulous position. Views amazing. Some of the friendliest and happiest staff we've come across. The rooms and dining area were spotless. Very impressed"

Reviewed on Jun 27, 2025

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Heights Hotel
The Aqua
The Aqua
3 out of 5
Castletown, Portland, England
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $174 total per night from Jul 3 to Jul 4
$174 total
Jul 3 - Jul 4
Total includes taxes and fees
7.8/10 Good! (188 reviews)
"Good location for Portland Harbour watersports and good value for money given a full breakfast was included in the price"

Reviewed on Jun 14, 2025

The Aqua
Fairhaven Hotel
Fairhaven Hotel
2.5 out of 5
Fairhaven Hotel, 37 Esplanade, Weymouth, England
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $119 total per night from Jul 6 to Jul 7
$119 total
Jul 6 - Jul 7
Total includes taxes and fees
8.4/10 Very Good! (610 reviews)
"We were very happy with the hotel, staff were very friendly and we got a lovely room - much better than expected! Thanks for a lovely stay!"

Reviewed on Jun 24, 2025

Fairhaven Hotel
See all 1,883 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.

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 0.6 miles 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 Essential Information

Language
English
Currency
British pounds sterling
Population
12,700
Max Temp Winter
50ºF
Max Temp Summer
65ºF
Top Sights
Weymouth Beach, Chesil Beach and Lulworth Cove Beach

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Frequently asked questions

How much does a Portland vacation package cost?
You'll find cheap prices from $812 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?
If you're hoping to snag a cheap Portland vacation package, consider planning a trip in March, April and December. You're likely to find better prices on hotels and airfares during these months --- ideal for travelers wishing to save money.
How many days is enough for Portland?
With a well-organized schedule, you can easily tick off the main Portland sights in a few days. But if you'd like to explore off the beaten track or take day trips, think about booking your Portland vacation for longer.
Is it worth booking a vacation package to Portland?
Popular for its history, views and watersports, a Portland vacation is a hit with all kinds of travelers. Be sure to check out major sights like Portland Bill Lighthouse and Weymouth and Portland National Sailing Academy, and consider renting a set of wheels for day trips to experience 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. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Portland.
  2. Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Portland.
  3. Organize your Portland getaway with Expedia's trip planning tool: Search for and book stays and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Portland together.
  4. Set the duration of your trip: 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, including any travel time.
  5. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find a Portland vacation package that brings all your bookings together.
  6. Add on excursions and experiences: Take a look at our travel guide to find some exciting things to do in Portland. Book tickets or make reservations in advance to save time and avoid the stress of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Portland vacation packages?
If you're like us, you love going away but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Portland vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.