Town Landing Holidays

Photo by Ed Gaffny

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    Save up to S$1,300 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Price found within the past 48 hours. Click for updated prices.
  • 50-inch flat-screen TV with cable channels
    Jul 13 - Jul 16

    The Docent's Collection at 178 Middle Street + Flight

    Downtown Portland
    3 nights
    2.0 star property
    10/10 - Exceptional (25 reviews)
    "Beautiful, clean, modern room with modern amenities. Had everything you could need in an apartment even, and was so close to old for, everything was walking distance Staff with beyond friendly, helpful, assisting, and courteous. If I could give 6/5 stars instead I would have"
    Reviewed May 29, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    Save 100% on your flight
    S$1,217
    S$919
    per traveller
    found 1 day ago
    The Docent's Collection at 178 Middle Street
  • Restaurant
    Jul 13 - Jul 16

    Portland Harbor Hotel + Flight

    Downtown Portland
    3 nights
    4.0 star property
    9.4/10 - Exceptional (1,759 reviews)
    "Staff was extremely gracious and helpful. From the valet to the front desk to the restaurant."
    Reviewed May 30, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    Save 100% on your flight
    S$1,344
    S$1,029
    per traveller
    found 1 day ago
    Portland Harbor Hotel
  • Premium bedding, individually decorated, individually furnished
    Jul 13 - Jul 16

    Blind Tiger Portland - Danforth Street. + Flight

    West End
    3 nights
    3.5 star property
    9.6/10 - Exceptional (184 reviews)
    "The only real issue was the distance from all of the attractions and restaurants. "
    Reviewed May 15, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    Save 100% on your flight
    S$2,308
    S$1,787
    per traveller
    found 1 day ago
    Blind Tiger Portland - Danforth Street.
  • Children’s activities
    Jul 13 - Jul 16

    Inn By The Sea + Flight

    Cape Elizabeth
    3 nights
    4.0 star property
    9.6/10 - Exceptional (317 reviews)
    "Very nice place, very cclean and friendly."
    Reviewed May 30, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    Save 100% on your flight
    S$2,119
    S$1,659
    per traveller
    found 1 day ago
    Inn By The Sea
  • Living area
    Jul 13 - Jul 16

    The Docent's Collection at 121 Middle Street + Flight

    Downtown Portland
    3 nights
    3.5 star property
    9.6/10 - Exceptional (326 reviews)
    "The property is great. The amenities are quality- nothing is cheap… kitchen is stocked & utensils are not flimsy- bedding is nice. Some good touches like under mount lighting in the bathroom that comes on as you walk in- the temperature is easy to keep constant (which is rare in units) it’s very walkable and the parking is easy ($60 per night). Lots of good. The unit itself is very nice. My only complaint is that the furniture is stained and filthy… one chair had caked food and hair (a good..."
    Reviewed May 27, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    S$1,223
    S$991
    per traveller
    found 1 day ago
    The Docent's Collection at 121 Middle Street

Top hotels in Town Landing

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is S$167 per night from 15 Jun to 16 Jun
S$167
15 Jun - 16 Jun
includes taxes & fees
8/10 Very Good! (1,472 reviews)
"This hotel was bad from the minute we arrived. I called early in week to see if there was a possibility to check in early because we had a long ride & had to catch a ferry for a memorial for a boss in Peaks Island, ME. When we arrived the 2 at front desk kind of laugh at me & looked at me like I ..."

Reviewed on 1 Jun, 2026

Clarion Hotel Portland Airport ME
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 S$402 per night from 7 Jun to 8 Jun
S$402
7 Jun - 8 Jun
includes taxes & fees
9.4/10 Exceptional! (1,759 reviews)
"Staff was extremely gracious and helpful. From the valet to the front desk to the restaurant."

Reviewed on 30 May, 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 S$391 per night from 7 Jun to 8 Jun
S$391
7 Jun - 8 Jun
includes taxes & fees
9.4/10 Exceptional! (1,224 reviews)
"Convenient and dog friendly."

Reviewed on 31 May, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,308 properties in Town Landing
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 Town Landing holiday package cost?
Custom build your Town Landing package from as low as . Choose from any combination of flights, hotels and rental cars to put together the getaway you've been dreaming about for ages. Don't forget to add on a few activities!
How do I get a cheap travel package to Town Landing?
Track down flights that suit your busy schedule, add a hotel room to your booking and watch how much you save with a Town Landing holiday package. It's that simple! From flights and hotels to tours and rental cars, Expedia makes travelling cheap and easy. And with over 550 air carriers and 1,000,000 hotel options around the world to select from, you won't be short of choice.
Where should I stay in Town Landing?
There's loads to do in Town Landing, so stay close to its top sights and treat yourself to more time sightseeing. Gilsland Farm Audubon Centre is one place to put on your to-do list.
How far in advance should I book my Town Landing holiday?
While not all air carriers advertise tickets early, you can usually start comparing international fares on Expedia up to 12 months in advance. This is when you can score some fantastic deals. If you're booking last minute, you might get lucky. Low prices occasionally become available only weeks prior to departure.
What does an Expedia Town Landing travel package include?
That depends on what you're looking for. If you're travelling alone, you might decide to bundle hotels and flights. Taking the whole family to Town Landing? A travel package including hotels, flights and rental cars might be a better fit. Expedia gives you the flexibility and freedom to customize your travel package.
What should I know before booking a Town Landing travel package?
Bundling your bookings into a Town Landing holiday package is the easiest way to organise your trip. Not only that, you'll save when you combine your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Town Landing Expedia holiday package?
Yes — that's one of the best things about an Expedia holiday package. You get to choose. We have access to more than 550 airline partners around the world, so you have options galore when arranging your Town Landing adventure.
If I'm not able to travel, can I cancel my Town Landing holiday package?
Yes, you can cancel your Town Landing booking if your plans have been upended. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

Things to do

Harbor Lights and Sights Cruise

Harbor Lights and Sights Cruise

S$68
per adult
90% of travellers recommend
Harbor Lights and Sights Cruise
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

S$19
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
See all activities in Falmouth

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.