How much does a Portland vacation package cost?

You'll find cheap prices from $697 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.

Portland Vacation Packages 2025/2026 from $662

Things to do in and around Portland

Portland, England, is a fantastic destination for outdoor enthusiasts, offering a range of activities like water sports, family-friendly outings, and scenic day trips. Visitors can enjoy beach vacations, explore fishing resorts, and partake in adventures at private country clubs. Whether you're looking for thrilling experiences or relaxing days by the sea, Portland has something for everyone to enjoy.

Shopping

For unique gifts, visit the Broadwindsor Craft and Design Centre, located 24 miles away from Portland. If you're up for a drive, this store offers a charming selection of handcrafted items and local artwork, perfect for souvenirs to remember your trip.

Recreation

At Greenhill Beach, enjoy tranquil walks along the shore and rejuvenating yoga sessions with breathtaking views. Weymouth Pavilion offers a cultural experience with vibrant performances, perfect for a romantic evening. For family fun, catch the latest films at Cineworld Weymouth while indulging in popcorn and comfy seating.

Adventure

At the Weymouth and Portland National Sailing Academy, immerse yourself in thrilling water sports surrounded by stunning coastal views. For hiking enthusiasts, the South West Coast Path Section 49 offers scenic trails 3 miles away, while the Osmington Roman Walk, located 6 miles away, provides breathtaking vistas and rich history.

Nightlife

Portland's nightlife is vibrant and inviting, with a mix of cozy pubs and lively bars. Visit The Royal Portland for a great selection of local ales, or head to The Cove for a unique cocktail experience. Enjoy live music at The Portland Arms for a fun night out.

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

Find the best attractions near Portland

Portland, England is perfect for outdoor enthusiasts and adventure seekers, offering stunning beaches, historic castles, and a charming harbor. Visitors can immerse themselves in local culture while enjoying a variety of activities tailored for those seeking beach fun and outdoor experiences. Don’t miss the chance to tour Portland, explore its attractions, and consider staying at one of the lovely resorts in the area for a memorable vacation.

Chesil Beach: Stretching for 18 miles, Chesil Beach offers stunning coastal views and a pebbly shoreline perfect for beachcombing. Enjoy the tranquil atmosphere and unique wildlife, making it an ideal spot for a peaceful day by the sea.
Weymouth Harbour: This picturesque harbor is a vibrant hub of activity, featuring charming shops and eateries. Enjoy scenic boat rides or simply relax by the water, soaking in the beautiful views of the surrounding cliffs and boats.
Weymouth Bay: Offering a stunning backdrop for outdoor activities, Weymouth Bay boasts golden sands and clear waters. Whether swimming, sunbathing, or exploring the coastal path, this bay is perfect for enjoying the great outdoors.

Best time to go to Portland

The best time to visit Portland is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. February is its coolest month on average. At this time, visitor numbers are average and weather is mostly with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	44.6°F (7.0°C)	Light Rain	Mostly	Low	Slightly Low
February	44.4°F (6.9°C)	Light Rain	Mostly	Average	Slightly Low
March	46.0°F (7.8°C)	Light Rain	Mostly	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	High	Slightly Low
November	50.9°F (10.5°C)	Light Rain	Mostly	Low	Average
December	47.3°F (8.5°C)	Light Rain	Mostly	Low	Average

Tips to save on your trip to Portland

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Portland.
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.