Parkside Holidays from £898

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Your Parkside Holiday

Festivals, markets and walking are just the start of the things to look forward to when you lock in a holiday package to Parkside. Whether you're seeking relaxation or adventure, this small neighbourhood has it all. Not sure where to go during your trip to Parkside? Nearby attractions such as Portland Museum of Art, University of Southern Maine and Victoria Mansion are excellent places to start. Stop dreaming and start doing. When you're ready to lock in your holiday to Parkside, Expedia is here to help.

Price found within the past 48 hours. Click for updated prices.
84 Main

84 Main

4 out of 5
Price was £1,113, price is now £898 per person
£898
per person
13 Mar - 20 Mar
found 1 day ago
Return direct flight included
London (LHR) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.

Reviewed on 29 Dec 2025

The McKernan Inn

The McKernan Inn

3 out of 5
Price was £1,292, price is now £1,002 per person
£1,002
per person
13 Mar - 20 Mar
found 1 day ago
Return direct flight included
London (LHR) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on 27 Dec 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Price was £1,873, price is now £1,505 per person
£1,505
per person
13 Mar - 20 Mar
found 1 day ago
Return direct flight included
London (LHR) to Portland (PWM)
9.4/10 Exceptional! (288 reviews)
Room was ready early friendly staff and room is better than expected

Reviewed on 16 Nov 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was £1,180, price is now £966 per person
£966
per person
13 Mar - 20 Mar
found 1 day ago
Return direct flight included
London (LHR) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Nice and clean hotel with a nice restaurant.

Reviewed on 1 Feb 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was £1,705, price is now £1,400 per person
£1,400
per person
13 Mar - 20 Mar
found 1 day ago
Return direct flight included
London (LHR) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The whole was cozy! Well curated style and knowledgeable staff.

Reviewed on 5 Jan 2026

Where to stay in Parkside

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

Downtown Portland

4 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 Wadsworth-Longfellow House.

Find hotels in Downtown Portland

Top hotels in Parkside

Longfellow Hotel

Longfellow Hotel

4 out of 5
754 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is £122 per night from 8 Feb to 9 Feb
£122
8 Feb - 9 Feb
includes taxes & fees
9.4/10 Exceptional! (142 reviews)
We loved our stay. Great staff, room was nice, cafe very good and the Town Car service for rides, so convenient!

Reviewed on 5 Jan 2026

Longfellow Hotel
The Francis

The Francis

3.5 out of 5
747 Congress Street Portland ME
Fully refundableReserve now, pay when you stay
The price is £109 per night from 9 Feb to 10 Feb
£109
9 Feb - 10 Feb
includes taxes & fees
9.4/10 Exceptional! (374 reviews)
Clean and great location

Reviewed on 11 Jan 2026

The Francis
Knock on Wood | Airy Charm in Heart of Downtown

Knock on Wood | Airy Charm in Heart of Downtown

Portland ME
The price is £259 per night from 5 Mar to 6 Mar
£259
5 Mar - 6 Mar
includes taxes & fees
8.8/10 Excellent! (25 reviews)
Easy in and out. Beds were super comfortable

Reviewed on 25 Oct 2025

Knock on Wood | Airy Charm in Heart of Downtown
See all 2,304 properties in Parkside
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 Parkside travel package cost?
Our Parkside packages, which begin at just £898, are an easy way to save big bucks. All you have to do is choose your preferred hotels, flights and more to create your dream escape.
If I'm not able to travel, can I cancel my Parkside travel package?
It's impossible to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Parkside travel package. If your booking was made in the last 24 hours, you may be eligible for a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal for more information.
How do I get a cheap travel package to Parkside?
Book everything all in one place with our Parkside travel packages. We have deals on hotels, flights and more that'll keep your pocketbook happy and your adventurous spirit busy. And, with more than 550 airlines and 1,000,000 hotels around the world to choose from, you have countless opportunities to mix and match as you want.
Does Expedia offer Book Now, Pay Later Parkside holidays?
We sure do. Expedia has partnered with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply pick the payment plan that suits you best during the checkout process and take away the stress of budgeting for your next trip. Don't forget to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that fit all budgets, so you can jet away on that well-earned holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your holiday across multiple transactions.
  • Low deposit holidays: Clicking the "book now" button is easier with this plan. Simply put down a small deposit on your holiday and then start packing your bags.

Where should I stay in Parkside?
Take the hassle out of sightseeing by staying someplace just a stone's throw away from Parkside's biggest attractions. University of Southern Maine and Portland Museum of Art are two of the best in this neighbourhood.
What are the top hotels in Parkside?
The Westin Portland Harborview and Embassy Suites by Hilton Portland Maine are two of the most popular properties in Parkside. Why not have a look at the amenities and rates at each and then make up your mind?
How far in advance should I book my Parkside holiday?
Travellers are usually able to browse international flights on Expedia within 12 months of the departure date. Booking late? With a bit of luck, it's still possible to purchase a cheap ticket just weeks before your flight.
What does an Expedia Parkside travel package include?
With Expedia, you can choose a combination of car rentals, flights and hotels to build your ideal Parkside package. Once you've made your booking, you can add on the fun stuff like day tours and activities. Don't forget, the more you bundle, the more discounts you'll get!
What should I know before booking a Parkside travel package?
Tailor deals to suit your budget with an Expedia package. Hotels, airfares, rental cars — we've got everything you need to plan your getaway. You'll save a packet just by bundling your bookings. Whether you're heading away on a ski trip or venturing someplace warm, your perfect holiday is just a few clicks away.
Can I choose my airline with a Parkside Expedia travel package?
Expedia has access to more than 550 partner airlines globally, so you sure can! Just select the carrier that suits you and craft the perfect Parkside trip.

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

£12
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

£18
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.