Default HTG hotel image

Cliff Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cliff Island vacation 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 CA $399
CA $665 total
includes taxes & fees
Aug 3 - Aug 4
City Amenities, Casco Bay Sunrises and Natural Beauty

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (54 reviews)
"Wonderful stay!"
United States
Erika T.
The price is CA $285
CA $518 total
includes taxes & fees
Jul 29 - Jul 30
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 CA $457
CA $499 total
includes taxes & fees
Jul 26 - Jul 27
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 CA $821
CA $1,106 total
includes taxes & fees
Jul 27 - Jul 28
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.
The price is CA $1,971
CA $2,744 total
includes taxes & fees
Aug 7 - Aug 8
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 CA $588
CA $1,040 total
includes taxes & fees
Jul 23 - Jul 24
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 CA $654
CA $818 total
includes taxes & fees
Aug 17 - Aug 18
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 CA $333
CA $536 total
includes taxes & fees
Jul 23 - Jul 24
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 CA $809
CA $1,165 total
includes taxes & fees
Jul 27 - Jul 28
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 CA $422
CA $658 total
includes taxes & fees
Aug 2 - Aug 3
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 CA $704
CA $1,070 total
includes taxes & fees
Jul 26 - Jul 27
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.
The price is CA $524
CA $1,004 total
includes taxes & fees
Jul 22 - Jul 23
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 CA $344
CA $540 total
includes taxes & fees
Jul 26 - Jul 27
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 CA $1,033
CA $1,540 total
includes taxes & fees
Aug 11 - Aug 12
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 CA $536
CA $825 total
includes taxes & fees
Aug 13 - Aug 14
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 CA $802
CA $1,227 total
includes taxes & fees
Jul 23 - Jul 24
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 CA $469
CA $724 total
includes taxes & fees
Jul 28 - Jul 29
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 CA $376
CA $559 total
includes taxes & fees
Aug 3 - Aug 4
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 CA $699
CA $1,485 total
includes taxes & fees
Jul 28 - Jul 29
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 CA $567
CA $987 total
includes taxes & fees
Aug 18 - Aug 19
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cliff Island Hotel Reviews

Find out more about Cliff Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cliff Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Cliff Island?

Yes, there are vacation rentals close to top sights in Cliff Island, or you can choose a more remote option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Cliff Island?

New Listing. 2BR+Bonus Sleeping Room in OOB. Walk to Beach & Amusement Park.: This vacation 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 larger area, you’ll find Fifth Maine Museum and Umbrella Cover Museum.

What are vacation rentals like in Cliff Island?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Cliff Island. Vacation rentals offer extras like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip.