A cityscape with a prominent church steeple, various buildings, and lush green trees.

Portland Vacations from $514

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Your Portland Vacation

When a break in the city is calling, answer it with a vacation package to Portland. The neighborhood of Parkside, which is great for festivals, markets and walking, makes a fantastic base for your adventures. Fill your free time with tours of Portland Head Light, University of Southern Maine and Portland Museum of Art, some of the top attractions you just have to see during your trip to Portland. Don't put off your visit to this destination any longer. Your perfect Portland vacation is just a few clicks away with Expedia.

The Latest Portland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 29 - Jan 3

    Dormir + Flight

    Windham
    5 nights
    3.0 star property
    9.0/10 - Wonderful (1,004 reviews)
    "I love this place. This is the 2nd time I've stayed here. It's clean, quiet, well located. The staff is friendly and helpful. I would recommend it to anyone."
    Reviewed November 3, 2026
    Roundtrip • Philadelphia (PHL) - Portland (PWM)
    PHL - BOS • Nonstop BOS - PHL • Nonstop
    $644
    $514
    per traveler
    found 1 day ago
    Dormir
  • Jan 22 - Jan 25

    Admiral Peary Inn + Flight

    Fryeburg
    3 nights
    3.0 star property
    8.8/10 - Excellent (70 reviews)
    "Very unique and fun history."
    Reviewed October 27, 2026
    Roundtrip • Houston (IAH) - Portland (PWM)
    IAH - MHT • 1 stop MHT - IAH • 1 stop
    $665
    $539
    per traveler
    found 1 day ago
    Admiral Peary Inn
  • Jan 15 - Jan 17

    Evalina Hotel + Flight

    Downtown Portland
    2 nights
    2.5 star property
    10/10 - Exceptional (18 reviews)
    "Fabulous rental! The location was great could walk to restaurants, shopping, sightseeing. Place was very clean, beds comfortable and stocked with everything you need. Thank you for a wonderful stay in Portland."
    Reviewed November 3, 2026
    Roundtrip • Dallas (DFW) - Portland (PWM)
    DAL - PWM • 1 stop PWM - DFW • 1 stop
    $988
    $820
    per traveler
    found 1 day ago
    Evalina Hotel
  • Jan 4 - Jan 7

    Waldo Emerson Inn + Flight

    Kennebunk
    3 nights
    3.0 star property
    9.4/10 - Exceptional (357 reviews)
    "Our stay at the Waldo Emerson was nothing short of exceptional! From the moment we arrived, Amelia welcomed us with warm hospitality, and every detail of this charming property made us feel right at home. The accommodations were comfortable and full of character, and the property itself is absolutely beautiful. Each morning, we looked forward to a delicious, fresh, and thoughtfully prepared breakfast that was the perfect start to our day. What truly made our experience special were the..."
    Reviewed October 18, 2026
    Roundtrip • Philadelphia (PHL) - Portland (PWM)
    PHL - BOS • Nonstop BOS - PHL • 1 stop
    $660
    $549
    per traveler
    found 22 hours ago
    Waldo Emerson Inn
  • Jan 4 - Jan 7

    Inn By The Sea + Flight

    Cape Elizabeth
    3 nights
    4.0 star property
    9.6/10 - Exceptional (345 reviews)
    Roundtrip • Philadelphia (PHL) - Portland (PWM)
    PHL - BOS • Nonstop BOS - PHL • 1 stop
    $699
    $589
    per traveler
    found 22 hours ago
    Inn By The Sea

Where to stay in and around Portland

Experience the charm of Portland, where outdoor adventures and waterfront attractions await. Explore vibrant neighborhoods west of downtown, perfect for family-friendly outings or a romantic getaway. For business travelers, finding the best stay near Portland ensures easy access to both urban vibes and scenic beauty.

South Portland

Discover South Portland, a welcoming destination perfectly suited for outdoor enthusiasts and families looking for a blend of relaxation and city excitement. With attractions like the historic Portland Head Light and opportunities for shopping and recreation, visitors can enjoy both leisure and culture. Located about 2 miles by car from Portland, South Portland makes for an ideal base to explore the region's vibrant offerings, ensuring a memorable stay for every traveler.

Downtown Portland

Experience the charm of Downtown Portland, an excellent hub for travelers who want to immerse themselves in the vibrant local culture and culinary scene. With attractions like the Cross Insurance Arena for thrilling events, the Portland Museum of Art showcasing stunning exhibits, and the picturesque East End Beach for relaxation, there’s something for everyone. Located around Portland, this area offers easy access to both urban excitement and scenic beauty, making Downtown Portland a smart choice for your stay.

Old Port

If you are a foodie or culture enthusiast, look no further than Old Port, a charming neighborhood in Portland, Maine, known for its vibrant arts scene and delicious dining options. You can explore the Portland Museum of Art, catch a show at the Cross Insurance Arena, or relax at East End Beach, all just a short stroll away. Located around Portland, Old Port offers easy access to scenic views and family-friendly activities. It’s a smart choice for your stay, blending convenience with rich local experiences.

Back Cove

Immerse yourself in Back Cove, where outdoor enthusiasts and families can easily access stunning scenery and recreational areas. This charming neighborhood around Portland offers delightful experiences, from exploring the beautiful lake and beach to enjoying events at the Cross Insurance Arena and the Portland Museum of Art. With its seasonal appeal, especially from July to September, Back Cove is a smart choice for travelers seeking a memorable vacation. Enjoy the perfect blend of nature and culture in this picturesque locale.

West End

Looking for the perfect spot? West End is ideal for travelers seeking a blend of culture, cuisine, and leisure during their stay in Portland, Maine. This vibrant neighborhood offers easy access to attractions like the Portland Museum of Art and the Cross Insurance Arena, along with scenic parks and family-friendly beaches. Located around Portland, West End provides a great base for exploring the city's artistic and outdoor offerings, making it a smart choice for your hotel booking.

Discover the most popular places to visit in Portland

What to do in Portland

Portland Hotel Deals

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.

Frequently Asked Questions

How much does a Portland vacation package cost?

You'll find cheap prices from $514 on Expedia for your Portland break. However, factors like your choice of hotel, the season 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 looking to score a cheap Portland vacation package, consider visiting in September, October and December. You'll usually find lower rates on airfares and hotels during these months — perfect for budget-conscious travelers.

How many days is enough for Portland?

Allow around 2 days for your Portland vacation if you want to discover all that makes this place special. Explore popular areas, including Nasons Corner and East Bayside. Then check out top attractions like East End Beach and Sand Beach. With a clever itinerary, you'll be kept busy with room for some downtime too. Want to go beyond Portland? Consider squeezing in an excursion or two.

Is it worth booking a vacation package to Portland?

Known for its walking trails, culture and plenty of other highlights, you can be certain Portland is a good vacation destination. Some of the top attractions to add to your itinerary? Don't miss Portland Museum of Art and Victoria Mansion during your Portland vacation.

How to find the best Portland package deals?

Start your search for a Portland package deal by entering your destination and travel dates under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Portland package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Portland escape off to a flying start.

Is it cheaper to book a Portland vacation as a package?

You can enjoy significant savings on your Portland retreat by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to browse the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.

When to book a vacation package to Portland?

Secure fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Portland escape.

How to plan a trip to Portland?

  1. Choose when to get away: Check your calendar and get packing. Your favorite time of year and the type of activities on offer will also help you decide when to visit Portland.
  2. Set a budget: Factor in costs such as flights, food and transportation when working out how much to save for your trip to Portland. Then, select a property that works with your budget, whether that's a wallet-friendly option or a high-end getaway.
  3. Explore Portland with our trip planning tool: Gain insights into the top attractions and best hotels for your trip to Portland. You can also save your must-visit places, collaborate with friends and family and organize your plans in one place.
  4. Decide your trip length: Consider how much time you want to spend discovering Portland. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  5. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Portland vacation package.
  6. Book any activities or day trips: Now to the fun part — organizing everything you want to see and do. Explore some of the best things to do in Portland and reserve your tickets in advance to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Portland vacation packages?

Jet off on your dream escape to Portland with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until the next payday — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up bargains while they last.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.