Cliff Island Holiday Rentals

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Holiday Rentals in Cliff Island

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (87)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is AU$422
includes taxes & fees
7 Dec - 8 Dec
The Weldon Hotel

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island
10.0 out of 10, Exceptional, (232)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Old Orchard Beach
9.8 out of 10, Exceptional, (45)
"Excellent family stay. Backyard is nice and shaded, you can see the ocean from the house and amenities are great. "
United States
Danielle N.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Old Orchard Beach
9.6 out of 10, Exceptional, (67)
"In one word AMAZING! We rented this property to gather our immediate family, adult children and grandchildren. We had a tragedy in our family as my oldest son was killed, this made our once close family, split apart. This property was so beautiful and such a happy place to be that my prayers were answered my family began the healing process. The location and the views one could not be unhappy. Thank you Jason for helping to make the stay amazing!"
United States
Helen F.
The price is AU$1,893
includes taxes & fees
18 Nov - 19 Nov
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Old Orchard Beach
9.8 out of 10, Exceptional, (97)
"The location was perfect and the house was exceptional. The host and property manager were very responsive and helpful. Would definitely recommend a stay!"
United States
Kathleen C.
The price is AU$1,732
includes taxes & fees
3 Dec - 4 Dec
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Studio Unit Walkable Everywhere

West Bayside
5.8 out of 10, (6)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
The price is AU$217
includes taxes & fees
18 Nov - 19 Nov
Studio Unit Walkable Everywhere

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Old Orchard Beach
9.8 out of 10, Exceptional, (12)
"Walking distance to the board walk. Clean and just enough space for 4 of us. Had everything we needed plus plenty of towels! "
United States
Natalia R.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

In-town no frills 2 bedroom apt

West Bayside
8.4 out of 10, Very good, (15)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
The price is AU$233
includes taxes & fees
18 Nov - 19 Nov
In-town no frills 2 bedroom apt

The Dollhouse

Old Orchard Beach
9.2 out of 10, Wonderful, (5)
"Wonderful stay for a small bachelorette party! Right squeeze with 7 girls but great to have the place already decorated. Very close to the pier and lots of stores, restaurants, and places to go around. Host was very friendly and accommodating, answered questions and was flexible with any of our needs!"
United States
Margaret D.
The price is AU$1,157
includes taxes & fees
18 Nov - 19 Nov
The Dollhouse

Gorgeous ocean-front home with stunning beach views

Old Orchard Beach
9.4 out of 10, Exceptional, (126)
"Loved the area. Close to shops and dining. Beach is absolutely beautiful. Perfect place for families."
United States
Victoria H.
Gorgeous ocean-front home with stunning beach views

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2.0 star property
Grand Beach
9.0 out of 10, Wonderful, (17)
"Great location. Beautiful view. Peaceful part of the beach. "
United States
Kristi N.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Old Orchard Beach
9.8 out of 10, Exceptional, (64)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Private Entrance Residential Portland

Deering Center
9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
United States
Michelle S.
Private Entrance Residential Portland

Sunny Modern Oasis in Portland’s Trendy East End

Munjoy Hill
10.0 out of 10, Exceptional, (62)
"Cozy, clean and quiet, within short walking distance to restaurants, coffee shops, breweries, distilleries and shopping. "
United States
Jane
Sunny Modern Oasis in Portland’s Trendy East End

Updated Long Island Maine Cottage

Long Island
10.0 out of 10, Exceptional, (7)
"Great island house! Loved how stocked the kitchen was, we had comfortable beds and even beach chairs and cooler. We would definitely stay here again. "
United States
Serra C.
Updated Long Island Maine Cottage

Fantastic Waterfront Views

West Point
9.6 out of 10, Exceptional, (14)
"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "
United States
Heather S.
The price is AU$416
includes taxes & fees
30 Nov - 1 Dec
Fantastic Waterfront Views

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Old Orchard Beach
9.8 out of 10, Exceptional, (224)
"The view off the deck was breathtaking "
United States
Raymond
The price is AU$522
includes taxes & fees
18 Nov - 19 Nov
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Beautiful Oceanfront House- Stunning Water Views

Harpswell
9.4 out of 10, Exceptional, (23)
"We loved our stay! Gorgeous view, lots of thoughtful little amenities. The home was extremely clean and the host was just lovely. "
United States
Catherine O.
Beautiful Oceanfront House- Stunning Water Views

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island
9.8 out of 10, Exceptional, (36)
"Lovely home with comfortable porch and bonfire area to enjoy outside. "
United States
Patti M.
Large, light filled 4 bedroom house - walk to ocean and ferry

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Falmouth
8.8 out of 10, Excellent, (6)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
United States
Darcie B.
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
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 favourite 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 depend 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 AU$217 per night. Entering your travel dates in the search wizard might find you 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 Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This holiday home rental outside of Cliff Island is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Cliff Island?

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

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.