Old Port Holidays from £1,506

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Your Old Port Holiday

Your next great adventure is calling with a holiday package to Old Port. Entertainment, food and great times — you're bound to find it in this neighbourhood. Wondering where to go during your trip to Old Port? Nearby attractions such as Portland Museum of Art, University of Southern Maine and Victoria Mansion are excellent places to start. Expedia will help you turn your ideal Old Port holiday into reality, no matter your budget or travel plans.

Price found within the past 48 hours. Click for updated prices.
Breakwater Inn

Breakwater Inn

4.5 out of 5
Price was £1,754, price is now £1,506 per person
£1,506
per person
4 May - 11 May
found 4 hours ago
Return flight included
London (LHR) to Portland (PWM)
8.4/10 Very Good! (53 reviews)
Room was wonderful,perfect. Staff could not have been nicer

Reviewed on 19 Dec 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was £2,183, price is now £1,742 per person
£1,742
per person
4 May - 11 May
found 4 hours ago
Return flight included
London (LHR) to Portland (PWM)
9.4/10 Exceptional! (686 reviews)
Historic, cozy, and charming mansions and rooms...our stay was amazing.

Reviewed on 15 Mar 2026

Grasshopper Inn

Grasshopper Inn

4 out of 5
Price was £2,600, price is now £2,138 per person
£2,138
per person
4 May - 11 May
found 4 hours ago
Return flight included
London (LHR) to Portland (PWM)
9.8/10 Exceptional! (71 reviews)
We had a fantastic stay at Grasshopper Inn and will definitely return when back in the area. Clean, friendly staff and brilliant location.

Reviewed on 22 Oct 2025

Stage Neck Inn

Stage Neck Inn

4 out of 5
Price was £2,233, price is now £1,918 per person
£1,918
per person
4 May - 11 May
found 4 hours ago
Return flight included
London (LHR) to Portland (PWM)
9.4/10 Exceptional! (522 reviews)
We loved our stay it was just perfect

Reviewed on 2 Jan 2026

Serenity by the Sea 180 Steps to the Beach!

Serenity by the Sea 180 Steps to the Beach!

4 out of 5
Wells Beach
Price was £1,780, price is now £1,540 per person
£1,540
per person
4 May - 11 May
found 4 hours ago
Return flight included
London (LHR) to Portland (PWM)
No reviews

Where to stay in Old Port

Find the best Old Port areas and neighborhoods for the activities you enjoy most. Learn more about Old Port
State Street Church

Downtown Portland

5 out of top 10 points of interest in this area
3.5/5(2 area reviews)

A noteworthy feature of Downtown Portland is its captivating waterfront views. While you're in town, be sure to stop and check out Cross Insurance Arena and Merrill Auditorium.

Find hotels in Downtown Portland

Top hotels in Old Port

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is £123 per night from 5 Apr to 6 Apr
£123
5 Apr - 6 Apr
includes taxes & fees
9.2/10 Wonderful! (1,772 reviews)
A very nice and unique hotel in a great location. Would definitely stay again.

Reviewed on 21 Mar 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (1,608 reviews)
We booked the Regency Hotel for a girls weekend, and it was awesome! The location is perfect! We booked two rooms, and both were spotless. The staff was friendly and accommodating. My niece had a spa treatment that she said was heavenly. We spent time at the Armory Lounge, and the bartender was as ...

Reviewed on 22 Mar 2026

Get rates
Portland Regency Hotel & Spa
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
433 Fore St Portland ME
Fully refundableReserve now, pay when you stay
The price is £82 per night from 25 Mar to 26 Mar
£82
25 Mar - 26 Mar
includes taxes & fees
9/10 Wonderful! (1,317 reviews)
Location is walkable to shops and restaurants. From the valet to the front desk the experience was great!

Reviewed on 23 Mar 2026

Hyatt Place Portland Downtown - Old Port Square
See all 2,316 properties in Old Port
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 an Old Port travel package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Old Port from just £1,506. And the more you bundle, the more dollars you save. The getaway of your dreams has never been so affordable.
If I'm not able to travel, can I cancel my Old Port travel package?
Because we understand life can be unpredictable, the answer is yes. For more information, visit our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to cancel or change it for free. Your airline, hotel or car rental company may charge a fee if your booking is older than that.
How do I get a cheap travel package to Old Port?
Combine your hotel and flight bookings, throw in extras such as activities or a rental car, and save with an Old Port travel package. You won't just walk away with awesome discounts on your escape — you'll have plenty of choice too. When you book through Expedia, you'll have your pick of over 550 airlines and 1,000,000 hotels around the world. Your affordable holiday begins right here, right now!
Does Expedia offer Book Now, Pay Later Old Port holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has devised a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book your dream getaway without draining your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that fit all budgets, so you can book that well-deserved holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your holiday in multiple transactions.
  • Low deposit holidays: Hitting the "book now" button is easier with this option. Just put down a small deposit on your holiday and then start packing your suitcase.

Where should I stay in Old Port?
Most people who travel to Old Port include University of Southern Maine and Portland Museum of Art on their bucket lists. Why not book a hotel near these fantastic attractions?
What are the top hotels in Old Port?
If it's your first time in Old Port, lock in a room at The Westin Portland Harborview or Embassy Suites by Hilton Portland Maine. Both offer comfortable beds and are top options with many savvy travellers.
How far in advance should I book my Old Port holiday?
Travellers are usually able to compare international flights on Expedia within 12 months of the departure date. Booking late? With a bit of luck, it's still possible to nab a cheap ticket just weeks before your journey.
What does an Expedia Old Port travel package include?
You can select from any combination of hotels, flights and rental cars. Once you've made your booking, you can also add on activities and tours. Want to pick your airfare class? That's possible too. The choice is yours when it comes to putting together your ideal Old Port trip.
What should I know before booking an Old Port travel package?
Whether it's adventure or relaxation you're craving, an Old Port travel package lets you plan your escape your way. Plus, you'll score great discounts when you combine your accommodation with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with an Old Port Expedia travel package?
Yes — that's the beauty of an Expedia package. You can pick and choose your flights, hotels and more. We have access to more than 550 airline partners throughout the world, so you have lots of choice when planning your Old Port trip.

Popular places to visit

Casco Bay Lines Ferry Terminal

Explore the waterfront in Portland with a trip to Casco Bay Lines Ferry Terminal. Discover the top-notch restaurants and great live music in this family-friendly area.

Casco Bay Lines Ferry Terminal

Things to do

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

£7
per traveller
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

£13
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
Portland Maine App-Based Driving & Walking Audio Tour Bundle

Portland Maine App-Based Driving & Walking Audio Tour Bundle

£19
per traveller
Portland Maine App-Based Driving & Walking Audio Tour Bundle
See all activities in Portland

* 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.