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Cliff Island Holiday Rentals

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Our top choices for Cliff Island holiday rentals

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (130 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
The price is NZ$817
includes taxes & fees
4 Aug - 5 Aug
City Amenities, Casco Bay Sunrises and Natural Beauty

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (56 reviews)
"Wonderful stay!"
United States
Erika T.
The price is NZ$620
includes taxes & fees
29 July - 30 July
Full sized home

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is NZ$760
includes taxes & fees
26 July - 27 July
Fortland Island Campground

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (5 reviews)
"Spacious, clean, and in the perfect location in Old Port."
United States
Celine
The price is NZ$1,373
includes taxes & fees
27 July - 28 July
Evalina Hotel

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (76 reviews)
"This is such a great house and it was perfect for our group! We would definitely stay there again "
United States
Catherine T.
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (66 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is NZ$1,238
includes taxes & fees
23 July - 24 July
Arlie`s Digs! - One Block To Willard Beach!

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (102 reviews)
"Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district."
United States
Kara
The price is NZ$950
includes taxes & fees
17 Aug - 18 Aug
The Weldon Hotel

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Jennifer’s VRBO is exactly as cute, clean and cozy as the listing’s photos depict. It is so well maintained that she has living house plants that are thriving 10/10. I can’t wait to stay again!"
United States
Liz P.
The price is NZ$750
includes taxes & fees
2 Aug - 3 Aug
Peaceful & minutes from the Old Port with private parking

Portland’s Best Ocean Views from a 40-Foot Private Deck

Portland’s Best Ocean Views from a 40-Foot Private Deck
Munjoy Hill
9.6 out of 10, Exceptional, (27 reviews)
"Beautiful location with easy walk to downtown. "
United States
Megan T.
The price is NZ$1,396
includes taxes & fees
4 Aug - 5 Aug
Portland’s Best Ocean Views from a 40-Foot Private Deck

Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (104 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is NZ$796
includes taxes & fees
2 Aug - 3 Aug
Ocean View East End Studio in a Historic Victorian

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (42 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$1,278
includes taxes & fees
20 Aug - 21 Aug
Modern & Sunny House Steps from the Promenade. Private Parking!

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Munjoy Hill
9.8 out of 10, Exceptional, (132 reviews)
"Home is in an excellent location, and as described. Easy communication with zero issues during stay. Great experience overall and will return! "
United States
Christina A.
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (30 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is NZ$651
includes taxes & fees
26 July - 27 July
Sunny Spot with Private Parking.

Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood
Munjoy Hill
9.8 out of 10, Exceptional, (39 reviews)
"We were four couples who enjoyed our weekend stay. Easy walk to downtown to delicious restaurants and shopping. "
United States
Kristin M.
The price is NZ$1,911
includes taxes & fees
11 Aug - 12 Aug
Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

Vintage Maine & Modern Convenience in Portlands Exclusive East End

Vintage Maine & Modern Convenience in Portlands Exclusive East End
Munjoy Hill
9.8 out of 10, Exceptional, (54 reviews)
"Great location. Short walk to Old Port and shops restaurants. Host was great"
United States
Jeff P.
The price is NZ$969
includes taxes & fees
13 Aug - 14 Aug
Vintage Maine & Modern Convenience in Portlands Exclusive East End

Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (12 reviews)
"It was a beautiful property with everything you could need available. There were a lot of little touches that made it really nice! "
United States
Jeannette B.
The price is NZ$1,448
includes taxes & fees
23 July - 24 July
Harborview - Curated East End Escape w/ Parking

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (180 reviews)
"Location was great. We walked to most places, kids love the trail and playground down the street. Parking on the street was easy. Beautiful front room with lots of natural light!"
United States
Gina F.
The price is NZ$878
includes taxes & fees
28 July - 29 July
Glorious getaway on Portland's Eastern Promenade.

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (138 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is NZ$684
includes taxes & fees
10 Aug - 11 Aug
Adorable Portland getaway on the Eastern Promenade

Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"What can I say about my stay; peaceful, beautiful views, and relaxing! Home was clean with modern finishes but super comfortable for my four guests. The downstairs area is very private from the main floor. The yard was a great space where we had our outdoor fire looking up at the stars at night. The deck was perfect for our family lunch and dinners. We took chairs down to the beach area to sit closer to the water which was perfect. It's super close to town, Wolfe's Neck and other amenities....
United States
Lisa E.
The price is NZ$1,805
includes taxes & fees
28 July - 29 July
Three bedroom in United States of America, Freeport

The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (100 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is NZ$1,166
includes taxes & fees
18 Aug - 19 Aug
The Globe House on Munjoy Hill - Walk to Breweries
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.
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Top Cliff Island Hotel Reviews

Find out more about Cliff Island

Everything you need to know about Cliff Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cliff Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cliff Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cliff Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cliff Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cliff Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cliff Island holiday rentals we have selected for you start as low as NZ$311 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cliff Island rentals

At Expedia, we put the best Cliff Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cliff Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cliff Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cliff Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Cliff Island?

Yes, there are holiday rentals close to the most popular sights in Cliff Island, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cliff Island has to offer?

New Listing. 2BR+Bonus Sleeping Room in OOB. Walk to Beach & Amusement Park.: This holiday home rental outside of Cliff Island is near the beach, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Cliff Island?

Explore the area and family-friendly sights such as Maine Narrow Gauge Railroad, or get out into nature at a spot like Sand Beach. In the wider area, you’ll find Fifth Maine Museum and Umbrella Cover Museum.

What are holiday rentals like in Cliff Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cliff Island. Holiday rentals provide amenities such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for small groups.