Chebeague Island Holidays from £1,204
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Chebeague Island Holiday
Book a Chebeague Island holiday package that has only the things you need and nothing you don't. Good for festivals, markets and walking, consider staying in the neighbourhood of Parkside. If a sightseeing tour is part of the programme during your trip to Chebeague Island, check out major attractions like Eagle Island, Little John Island Preserve and Sturdivant Island. That dream Chebeague Island holiday is a couple of clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored to suit your style.
Top Chebeague Island Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Cambria Hotel Portland Downtown-Old Port
Downtown Portland
Price was £1,300, price is now £1,204 per person
£1,204
per person
12 Aug - 15 Aug
found 1 hour ago
Return direct flight included
London (LON) to Portland (PWM)
9.4/10 Exceptional! (1,241 reviews)
I loved staying at Cambria in Portland. The location was perfect; the rooms were spacious and clean. The pillows were really comfortable. The staff was excellent.
Reviewed on 20 Jun 2026
Canopy by Hilton Portland Waterfront
Downtown Portland
Price was £1,663, price is now £1,453 per person
£1,453
per person
12 Aug - 15 Aug
found 1 hour ago
Return direct flight included
London (LON) to Portland (PWM)
9.4/10 Exceptional! (1,006 reviews)
small problem with the ac of the room, but we got switched to another room and that worked perfectly
Reviewed on 16 Jun 2026
Hampton Inn Portland Downtown - Waterfront
Downtown Portland
Price was £1,391, price is now £1,235 per person
£1,235
per person
12 Aug - 15 Aug
found 1 hour ago
Return direct flight included
London (LON) to Portland (PWM)
8.8/10 Excellent! (1,007 reviews)
Friendly staff. Big, clean and bright room with excellent aircon. Gym and small pool were very nice bonus, plus the self -service laundry room. Great location minutes from the waterfront
Reviewed on 17 Jun 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
Price was £1,750, price is now £1,558 per person
£1,558
per person
12 Aug - 15 Aug
found 1 hour ago
Return direct flight included
London (LON) to Portland (PWM)
9.8/10 Exceptional! (32 reviews)
Loved the room, location and service!
Reviewed on 6 Jun 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was £1,663, price is now £1,523 per person
£1,523
per person
12 Aug - 15 Aug
found 1 hour ago
Return direct flight included
London (LON) to Portland (PWM)
9.6/10 Exceptional! (328 reviews)
Such a great, different, non-hotel feeling option to stumble upon when I was in Portland, Maine. GREAT location. Feels much more boutique hotel like, quaint, way more appeal than a big "chain" hotel. I would want to book for more than a week to be able to use kitchen and flexibility of apartment-like feel.
Reviewed on 12 Jun 2026
Chebeague Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 21ºC |
Top Sights | State Theatre, East End Beach and Portland Museum of Art |
Top hotels in Chebeague Island
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
The price is £116 per night from 29 Jun to 30 Jun
£116
29 Jun - 30 Jun
includes taxes & fees
8.6/10 Excellent! (2,198 reviews)
"The property was very clean and quiet. The outside parking was ample and the surface had just been re-paved. The room was clean and comfortable, the a/c worked great and we had plenty of hot water with adequate water pressure. Breakfast was simple (bagels, waffle, cereal, eggs/sausage)but adequate. ..."
Reviewed on 19 Jun 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is £245 per night from 28 Jun to 29 Jun
£245
28 Jun - 29 Jun
includes taxes & fees
9.4/10 Exceptional! (1,764 reviews)
"We didn't sleep! The AC unit banged and shuttered and roared every time it shut on throughout the night and literally made the room unsleepable. I mentioned it to the receptionist at the front desk the next morning and there was no follow up or response. It was an expensive room that we booked on ..."
Reviewed on 18 Jun 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is £261 per night from 30 Jun to 1 Jul
£261
30 Jun - 1 Jul
includes taxes & fees
9.4/10 Exceptional! (1,249 reviews)
"I loved staying at Cambria in Portland. The location was perfect; the rooms were spacious and clean. The pillows were really comfortable. The staff was excellent."
Reviewed on 20 Jun 2026
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.
Explore a world of travel with Expedia
- 3 Star Hotels in Cousins Island
- Gay-Friendly Hotels in Bailey Island
- Bailey Island Hotels
- Condo Rentals in Casco Bay Islands
- Hotels with Parking in Casco Bay Islands
- Luxury Hotels in Casco Bay Islands
- Casco Bay Islands Hotels
- Villas in Casco Bay Islands
- Apartments in Cousins Island
- Best Western Hotels in Cousins Island
- Independent Hotels in Cousins Island
- Luxury Hotels in Cousins Island
- Cumberland Foreside Hotels
- Hotels near Eartha
- Falmouth Foreside Hotels
- Serviced Apartments in Great Diamond Island
- B&B in Great Diamond Island
- Caravan Parks in Great Diamond Island
- Hostels in Great Diamond Island
- Resorts in Great Diamond Island
- Beach Resorts & in Great Diamond Island
- Cheap Hotels in Great Diamond Island
- Business Hotels in Great Diamond Island
- Family-Friendly Hotels in Great Diamond Island
- Hotels with Gym in Great Diamond Island
- Luxury Hotels in Great Diamond Island
- Pet-Friendly Hotels in Great Diamond Island
- Romantic Hotels in Great Diamond Island
- Spa Hotels in Great Diamond Island
- Great Diamond Island Hotels
- Inns in Great Diamond Island
- Hotels near Land's End Gift Shop
- Holiday Homes in Littlejohn Island
- Caravan Parks in Long Island
- Long Island Hotels
- Peaks Island Hotels
- B&B in Yarmouth
- Yarmouth Hotels
- Bailey Island Bridge
- Bailey Island Holidays
- Visit Bailey Island
- Brunswick Holidays
- Cannon Rock
- Casco Bay Islands Holidays
- Visit Casco Bay Islands
- Casco Bay Lines Ferry Terminal
- Chocolate Church
- Cliff Walk
- Visit Cumberland Foreside
- Downtown Portland Holidays
- East End Beach
- Falmouth Holidays
- Fort Williams Park
- Gorham Holidays
- Great Diamond Island Holidays
- Visit Great Diamond Island
- Hermit Island Holidays
- Higgins Beach
- International Cryptozoology Museum
- Little John Island Preserve
- Maine Narrow Gauge Railroad Company and Museum
- Mclellan-Sweat Mansion
- Visit Peaks Island
- Portland Exposition Building
- Portland Head Light
- Portland Holidays
- Prouts Neck
- Scarborough Beach State Park
- Scarborough Holidays
- Sewell Pond Conservation Area
- Topsham Holidays
- Waterfront Park
- Windham Holidays
- All inclusive Holiday Packages Casco Bay Islands
- Beach Holiday Packages Cousins Island
- Golf Holiday Packages Cousins Island
- Romantic Holiday Packages Cousins Island
- Alamo Rent A Car Rental Cars in Cousins Island
- Apex Car Rentals Rental Cars in Great Diamond Island
- Avis Rental Cars in Casco Bay Islands
- Avis Rental Cars in Cousins Island
- Budget Rental Cars in Cousins Island
- Centauro Rental Cars in Cousins Island
- Car hire Yarmouth
- Firefly EU Rental Cars in Cousins Island
- Firefly Portugal Rental Cars in Cousins Island
- First Car Rental Rental Cars in Cousins Island
- Hertz Rental Cars in Cousins Island
- Interrent Rental Cars in Casco Bay Islands
- Midsize Car Hire in Cousins Island
- Mini Car Hire in Cousins Island
- Minivan Car Hire in Cousins Island
- Owners Rental Cars in Cousins Island
- Priceless Car Rental Rental Cars in Cousins Island
- Sicily By Car Rental Cars in Cousins Island
- Thai Cars Rental Cars in Great Diamond Island
- Thrifty Car Rental Rental Cars in Cousins Island
- People Carrier Car Hire in Great Diamond Island
* 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.
