Portland Vacation Packages 2026 from $1,450

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.

Residence Inn by Marriott London Bridge

London City Centre

$1,450

per person

Dec 12 - Dec 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to London (LHR)

9/10 Wonderful! (791 reviews)

I spent 26 days here. It was good value and very convenient location. The staff were nice. Unfortunately, I had my backpack with my work laptop stolen from the breakfast space. I was away from the table for less than 4 minutes. cctv shows the man walking in the lobby, walking through the restaurant, picking up my bag and walking out. while I was there someone else had their mobile phone taken out of their hand while standing in front of the hotel. This unfortunately is common in London. I was not happy with the security (and told the front desk). Anyone can get to a guest floor. You don’t need your room key to get into the ground floor stairwell or through the doors on guest floors. And there is no security downstairs.while the front desk is immediately in front of the doors, many times they are not watching and often I walked in without anyone seeing me. Housekeeping wasn’t the greatest. As this had a kitchen they provide you with a kitchen towel (same as a bath and hand towel for the bathroom). When the kitchen towel needed replacing I put it on the floor, they put it back on the counter. The next time I put it with more towels. They took it and didn’t replace. I also came home to the rubbish bin perched on my line of shoes which I had along the wall. I use my own silk pillowcase to sleep on, every time they made the bed (I didn’t choose housekeeping every day) they put that pillowcase (the obvious one I use) behind. All this to say it was convenient.

Reviewed on Oct 4, 2026

Residence Inn by Marriott London Kensington

London City Centre

Save 100% on your flight

$1,550

per person

Dec 12 - Dec 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to London (LHR)

8.6/10 Excellent! (1,360 reviews)

Hotel Riu Plaza London Victoria

London City Centre

Save 100% on your flight

$1,633

per person

Dec 13 - Dec 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to London (LHR)

9/10 Wonderful! (4,106 reviews)

Our room was spotlessly clean with a great bed! The location to shopping, restaurants and Victoria station was perfect for us!

Reviewed on Oct 12, 2026

Hotel Riu Plaza London The Westminster

London City Centre

$1,653

per person

Dec 13 - Dec 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to London (LHR)

9/10 Wonderful! (2,099 reviews)

Great staff...Vjay and Amelia stood out!

Reviewed on Oct 12, 2026

Residence Inn by Marriott London Tower Bridge

London City Centre

$1,621

per person

Nov 22 - Nov 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to London (LHR)

8.6/10 Excellent! (1,000 reviews)

Great location and very quiet

Reviewed on Sep 23, 2026

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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 lively bars.

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A rocky coastline with waves crashing against the rocks.

Portland Bill

9.0/10 (88 reviews)

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

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A rocky beach with waves crashing onto the shore and a cliff in the background.

Church Ope Cove

8.4/10 (32 reviews)

Why not spend a carefree afternoon at Church Ope Cove during your travels in Portland? While you're here, you can savor the top-notch restaurants.

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Portland Harbour

9.0/10 (10 reviews)

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

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Weymouth and Portland National Sailing Academy

9.2/10 (5 reviews)

Enjoy the collegiate vibe when you visit Weymouth and Portland National Sailing Academy, during your travels in Portland. Wander the area's beautiful beaches or simply enjoy one of its lively bars.

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Portland Castle

8.4/10 (7 reviews)

Portland Castle is just one of the places to see in Portland, so why not enjoy the other things to explore during your travels? Wander the area's beautiful beaches or simply enjoy one of its lively bars.

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Royal Manor Theatre

10.0/10 (1 review)

You can make plans for a show at Royal Manor Theatre during your trip to Portland. Wander the beautiful beaches and seaside in the area.

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The Olympic Rings Stone Sculpture

7.4/10 (6 reviews)

You can find out about the history of Portland with a visit to The Olympic Rings Stone Sculpture. While you're here, you can savor the top-notch restaurants.

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What to do in Portland

SEA LIFE Weymouth

$23

per adult

Portland Jurassic Coast Guided Mini Bus Excursions

JURASSIC COAST ADVENTURE - Guided Mini Bus Excursion-Small Groups

$214

per adult

Half-Day Guided E-Bike Tour Portland with Brunch

Guided E-Bike Tour of the Isle of Portland, Dorset

$173

per adult

See all activities in Portland

Portland Hotel Deals

Heights Hotel

Yeates Road Portland England

$121 nightly

$145 total

Nov 1 - Nov 2

Total with taxes and fees

8.4/10 Very Good! (728 reviews)

"Very friendly and welcoming staff on arrival. Nice Reception area, but once you get beyond the reception the corridors and our room (203) were somewhat austere. Nice breakfast, but a wider selection of fresh fruit salad would be very welcome. The red berries were still frozen but the cooked breakfast ..."

Reviewed on Oct 11, 2026

Coastal bungalow retreat on the Jurassic Coast at Portland, Dorset.

Portland Dorset

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Beautiful, family friendly Cottage with sea views of Chesil Beach

Fortuneswell ENG

9.2/10 Wonderful! (34 reviews)

"All good and nice spot. Parking is sometimes a bit challenging but manageable. A dishwasher would had been better than a washing machine in the kitchen but obviously that depends on personal preferences.The ice machine was great to have."

Reviewed on Sep 8, 2026

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See all 2,179 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

Things to do in and around Portland

Portland, England offers a variety of outdoor and adventure activities perfect for your vacation. Enjoy thrilling water sports, relax at a country private club, and explore educational attractions. Ideal for families, the area features exciting day trips, family-friendly tours, beach vacations, and fishing resorts, ensuring a memorable experience for everyone.

Shopping

For a unique shopping experience, explore local treasures at the Portland Market, where you can find handmade crafts and local produce. If you're up for a drive, visit the Broadwindsor Craft and Design Centre, 24 miles away, for a wider selection of artisanal gifts and souvenirs.

Recreation

Experience tranquility at Greenhill Beach, just 5 miles from Portland, where you can unwind on the sandy shores and soak in the soothing ocean vibes. For family-friendly entertainment, catch a show at Weymouth Pavilion, located 4 miles away, or enjoy a movie at Cineworld Weymouth, also 5 miles from Portland.

Adventure

Experience the Osmington Roman Walk, a stunning 6-mile hiking trail with breathtaking scenery. Head to the Weymouth and Portland National Sailing Academy for thrilling water sports right in Portland. Don’t miss the South West Coast Path Section 49 Trailhead, a scenic 3-mile hike perfect for outdoor enthusiasts.

Nightlife

Portland's nightlife offers a vibrant mix of pubs and live music. Check out the Boat Café for a relaxed drink by the water, or head to the Royal George for a lively atmosphere and local brews. For a dance scene, try the Portland Club, where DJs keep the energy high.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Portland

Portland, England, is perfect for outdoor and adventure vacations, offering stunning scenery and a blend of culture. Explore local attractions like beautiful beaches, historic castles, and bustling harbors. Whether you're seeking a relaxing beach day or a cultural experience, Portland has something for everyone. Don't miss out on guided tours and local resorts to enhance your visit and make the most of your time in this charming coastal town.

Chesil Beach: Experience the stunning beauty of Chesil Beach, a unique pebble beach stretching along the coast. Perfect for a leisurely stroll, this spot offers breathtaking views and a serene atmosphere, making it ideal for relaxation and beach vibes.
Weymouth Harbour: Just a short distance away, Weymouth Harbour is a picturesque spot where you can enjoy beautiful scenery and vibrant local life. Explore the charming waterfront, indulge in fresh seafood, or take a boat tour to soak in the coastal views.
Portland Bill Lighthouse: Visit the historic Portland Bill Lighthouse, a symbol of maritime history. Climb to the top for panoramic views of the coastline and learn about its fascinating past and cultural significance in the region.

Best time to go to Portland

The best time to visit Portland can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Portland falls in August, when visitor numbers are high and weather is mostly sunny with light rain. The coolest average temperature in Portland falls in February, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	44.6°F (7.0°C)	Light Rain	Mostly Cloudy	Low	Slightly Low
February	44.4°F (6.9°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
March	46.0°F (7.8°C)	Light Rain	Mostly Cloudy	Average	Average
April	49.1°F (9.5°C)	Light Rain	Mostly Sunny	Average	Average
May	53.8°F (12.1°C)	Light Rain	Mostly Sunny	Average	Average
June	58.8°F (14.9°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	62.2°F (16.8°C)	Light Rain	Mostly Sunny	High	Slightly High
August	62.4°F (16.9°C)	Light Rain	Mostly Sunny	High	Slightly High
September	60.3°F (15.7°C)	Light Rain	Mostly Sunny	Average	Average
October	56.5°F (13.6°C)	Light Rain	Mostly Cloudy	High	Slightly Low
November	50.9°F (10.5°C)	Light Rain	Mostly Cloudy	Low	Average
December	47.3°F (8.5°C)	Light Rain	Mostly Cloudy	Low	Average

Tips to save on your trip to Portland

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling during the off-peak season (typically January to February and October) for more affordable package holidays to Portland.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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 $1,450 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?

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.
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.
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.
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.
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.
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.

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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.

Portland Vacations from $1,450

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Your Portland Vacation

The Latest Portland vacation packages

Residence Inn by Marriott London Bridge

Residence Inn by Marriott London Kensington

Hotel Riu Plaza London Victoria

Hotel Riu Plaza London The Westminster

Residence Inn by Marriott London Tower Bridge

Stay near popular Portland attractions

Portland Bill Lighthouse

Portland Bill

Church Ope Cove

Portland Harbour

Weymouth and Portland National Sailing Academy

Portland Castle

Royal Manor Theatre

The Olympic Rings Stone Sculpture

What to do in Portland

SEA LIFE Weymouth

JURASSIC COAST ADVENTURE - Guided Mini Bus Excursion-Small Groups

Guided E-Bike Tour of the Isle of Portland, Dorset

Portland Hotel Deals

Heights Hotel

Coastal bungalow retreat on the Jurassic Coast at Portland, Dorset.

Beautiful, family friendly Cottage with sea views of Chesil Beach

Find the Best Portland Vacation Packages

Things to do in and around Portland

Find the best attractions in and around Portland

Best time to go to Portland

Tips to save on your trip to Portland

Portland Beach Vacation

Things You Should Know About Portland

Portland Essential Information

More vacations you might like

Frequently asked questions

Explore a world of travel with Expedia