Downtown Portland Holidays

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Your Downtown Portland Holiday

Experience the best that Downtown Portland offers with a Downtown Portland holiday package. From its markets to every other thing that makes it stand out, this neighbourhood will delight you from beginning to end. Some top nearby attractions to visit during your trip to Downtown Portland include Portland Museum of Art, University of Southern Maine and Victoria Mansion. Stop daydreaming and start doing. When it's time to lock in your holiday to Downtown Portland, Expedia will help you get there.

Price found within the past 48 hours. Click for updated prices.
  • Standard Room, 1 King Bed | Desk, iron/ironing board, cots/infant beds, rollaway beds
    Aug 3 - Aug 7

    Super 8 by Wyndham Lewiston Auburn Area + Flight

    Lewiston
    4 nights
    2.0 star property
    5.8/10 - (517 reviews)
    Return • New York (LGA) - Boston (BOS)
    LGA - BOS • Direct BOS - EWR • Direct
    £376
    £319
    per traveller
    found 8 hours ago
    Super 8 by Wyndham Lewiston Auburn Area
  • Lobby sitting area
    Sep 4 - Sep 7

    Ogunquit River Inn & Suites + Flight

    Ogunquit
    3 nights
    3.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "Nice place!"
    Reviewed June 7, 2026
    Return • London (LHR) - Boston (BOS)
    LHR - BOS • 1 stop BOS - LHR • 1 stop
    £1,131
    £824
    per traveller
    found 1 day ago
    Ogunquit River Inn & Suites
  • Lobby
    Aug 3 - Aug 7

    Best Western Freeport Inn + Flight

    Freeport
    4 nights
    3.0 star property
    7.8/10 - Good (1,007 reviews)
    "We liked the location, some rooms have a very nice view (ours was not one of them. Very dark with a basement style window facing tire level of the parking lot). Plenty of parking and a very good breakfast/lunch restaurant on site. Road construction made it difficult to access/leave, but that is not the hotel's fault. There was trenching dug around the property, clearly pipe problems, and the hotel smelled "sewery." Our toilet was leaking at the base and would not stop running all day and night...."
    Reviewed June 8, 2026
    Return • New York (LGA) - Boston (BOS)
    LGA - BOS • Direct BOS - EWR • Direct
    £405
    £336
    per traveller
    found 8 hours ago
    Best Western Freeport Inn
  • Property amenity
    Aug 3 - Aug 7

    Best Western York Inn + Flight

    York
    4 nights
    2.5 star property
    8.4/10 - Very good (1,001 reviews)
    "Breakfast awesome, room clean as a whistle plenty parking Sign getting on and off RT 1 could be a little better"
    Reviewed June 4, 2026
    Return • New York (LGA) - Boston (BOS)
    LGA - BOS • Direct BOS - EWR • Direct
    £422
    £362
    per traveller
    found 8 hours ago
    Best Western York Inn
  • King Room | Egyptian cotton sheets, premium bedding, memory-foam beds
    Aug 3 - Aug 7

    USA Inn + Flight

    Wells
    4 nights
    2.5 star property
    8.0/10 - Very good (786 reviews)
    "L emplacement est parfait"
    Reviewed June 8, 2026
    Return • New York (LGA) - Boston (BOS)
    LGA - BOS • Direct BOS - EWR • Direct
    £418
    £361
    per traveller
    found 8 hours ago
    USA Inn

Where to stay in Downtown Portland

Find the best Downtown Portland areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Portland
Old Port

Old Port

5/5(5 area reviews)

Explore the cobblestone streets in Portland’s historic district, which combines a wealth of history with a thoroughly modern city experience.

Find hotels in Old Port

Top hotels in Downtown Portland

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
The price is £263 per night from 14 Jun to 15 Jun
£263
14 Jun - 15 Jun
includes taxes & fees
9.4/10 Exceptional! (1,780 reviews)
"The only thing I can complain about is the attitude of the bartender. Everyone else has pleasant helpful."

Reviewed on 9 Jun 2026

Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
The price is £236 per night from 14 Jun to 15 Jun
£236
14 Jun - 15 Jun
includes taxes & fees
9.4/10 Exceptional! (1,241 reviews)
"This is such a nice property and a great location. We’ve stayed here twice and I wouldn’t hesitate to book again. Clean and comfortable."

Reviewed on 8 Jun 2026

Cambria Hotel Portland Downtown-Old Port
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
The price is £207 per night from 11 Jun to 12 Jun
£207
11 Jun - 12 Jun
includes taxes & fees
9.4/10 Exceptional! (1,684 reviews)
"We had a great stay at the Regency. Our room was very comfortable and the location is ideal, right in the Old Port with many excellent restaurants, fun stores, and the waterfront steps away. Very friendly and helpful staff. We appreciated the airport shuttle. Our only disappointment was that the ..."

Reviewed on 9 Jun 2026

Portland Regency Hotel & Spa
See all 2,421 properties in Downtown 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Downtown Portland travel package cost?
Be ready to book, because a trip to Downtown Portland starts from a tempting . When you combine your hotels, flights and car rentals into a package, you'll score the best prices.
If I'm not able to travel, can I cancel my Downtown Portland travel package?
You can. We get that life happens, so we're happy to help if you have to make changes to your Downtown Portland travel package. It may be possible to change or cancel your itinerary at no cost if you've booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if your booking was made more than 24 hours ago. Visit our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Downtown Portland?
If you love getting an amazing deal, combine your bookings into a Downtown Portland travel package. Whether you're looking for flights, hotels, activities or rental cars, you can browse and book them all in one place. You'll have ample choice at your fingertips as well. Expedia has more than 550 partner airlines and 1,000,000 hotel options throughout the world to choose from. Fly with who you want, stay wherever you like and save precious dollars — now that's the ideal getaway!
Does Expedia offer Book Now, Pay Later Downtown Portland holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has devised a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a dream getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that work for all types of budgets, so you can book that well-deserved holiday sooner.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan from Klarna.

Where should I stay in Downtown Portland?
Most who travel to Downtown Portland include University of Southern Maine and Portland Museum of Art on their bucket lists. Why not choose a hotel as close as possible to these great attractions?
What are the top hotels in Downtown Portland?
The Westin Portland Harborview and Embassy Suites by Hilton Portland Maine are two of the most well-known properties in Downtown Portland. Why not look up the amenities and rates at each and then make up your mind?
How far in advance should I book my Downtown Portland holiday?
It can be hard to know when is the perfect time to book your trip to Downtown Portland. But typically the earlier you book, the better the prices. In some cases, you can lock in your flights and hotels nearly a year prior to your departure date. If you're eager to escape on a last-minute getaway, no need to panic! There are incredible bargains popping up on Expedia every single day.
What does an Expedia Downtown Portland travel package include?
Hotels, flights and rental cars — we've got them well covered. With Expedia, you can shape your Downtown Portland travel package the way you like it. All you have to do is decide exactly what you need. Once you've made your booking, you can add on fun things like activities and tours. The more you bundle, the bigger the savings!
What should I know before booking a Downtown Portland travel package?
Bundling your bookings into a Downtown Portland travel package is the most convenient way to organise your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Downtown Portland Expedia travel package?
Yes, and with more than 550 airlines to choose from all over the world, you've got lots of choice. Scroll through the available options and find out which airline best suits your needs and budget.

Popular places to visit

East End Beach

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach

International Cryptozoology Museum

You can spend time studying the exhibits at International Cryptozoology Museum during your trip to Portland. Stroll along the area's waterfront or experience its entertainment choices.

International Cryptozoology Museum

Maine Narrow Gauge Railroad

You can spend an afternoon studying the exhibits at Maine Narrow Gauge Railroad in Portland. Experience the area's great live music and acclaimed theatre scene.

Maine Narrow Gauge Railroad

Things to do

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

£11
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
Small Group Afternoon Lighthouse Boat Cruise With Local Drinks

Small Group Afternoon Lighthouse Boat Cruise With Local Drinks

£64
per adult
Small Group Afternoon Lighthouse Boat Cruise With Local Drinks
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

£13
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
See all activities in Portland

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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. Flight-inclusive packages are ATOL protected.