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Cliff Island Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Cliff Island holiday rentals

A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

1. Great suburban location close to town!

Great suburban location close to town!
Deering Center
10.0 out of 10, Exceptional, (2 reviews)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
The price is HK$589
HK$760 total
includes taxes & fees
25 Oct - 26 Oct
Great suburban location close to town!
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

2. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.2 out of 10, Very good, (15 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
The price is HK$700
HK$871 total
includes taxes & fees
27 Oct - 28 Oct
Portland 1-bedroom with enclosed porch & parking
A dining table with chairs, a potted plant, and decorative items.

3. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (9 reviews)
"Location and parking were perfect for our first visit to Portland"
United States
Linda
The price is HK$1,122
HK$2,464 total
includes taxes & fees
25 Oct - 26 Oct
Willard Beach–Apartment Near Portland & Parks
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

4. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (21 reviews)
"We had a great stay in Portland! The place was just as described and the hosts were easy to communicate with. A good place for a couple nights within walking distance of all Portland has to offer."
United States
Lucy T.
The price is HK$618
HK$1,181 total
includes taxes & fees
3 Nov - 4 Nov
Studio Apartment near downtown Walkable!
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

5. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is HK$1,411
HK$3,426 total
includes taxes & fees
27 Oct - 28 Oct
Orchid Harbor, Bailey Island 3BR
A living room with a sofa, armchairs, a coffee table, and a potted plant.

6. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.8 out of 10, Excellent, (33 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is HK$726
HK$1,433 total
includes taxes & fees
9 Nov - 10 Nov
Beautiful 1st Floor Apartment & Amazing Shower
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

7. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is HK$824
HK$1,701 total
includes taxes & fees
8 Nov - 9 Nov
Mid Coast Getaway w/ water views
A kitchen with wooden cabinets, a stainless steel sink, and a potted plant.

8. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (29 reviews)
"Lovely apartment, in a pristine location. Very spacious and comfortable all around. Highly recommended this place for your next stay in Portland, Maine!"
United States
Gintare V.
The price is HK$762
HK$1,472 total
includes taxes & fees
3 Nov - 4 Nov
Bright & Spacious Apartment with Amazing Shower
A two-story house with a covered porch, a garage, and a front yard with potted plants.

9. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (174 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
The price is HK$746
HK$984 total
includes taxes & fees
3 Nov - 4 Nov
Large suite/private bath/private entrance on quiet street near Thomas Bay
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

10. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
The price is HK$981
HK$1,813 total
includes taxes & fees
10 Nov - 11 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A street lined with buildings, one with a red door and a sign that reads "MINATO".

11. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (153 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is HK$1,389
HK$2,267 total
includes taxes & fees
26 Oct - 27 Oct
Adorable Portland getaway on the Eastern Promenade
A covered porch with a view of a lake and trees.

12. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is HK$1,668
HK$3,717 total
includes taxes & fees
25 Oct - 26 Oct
Mere Point Sunrise Views at Eastern Shore!
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

13. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (125 reviews)
"Really nice room and location"
United States
Victoria
The price is HK$1,523
HK$2,249 total
includes taxes & fees
2 Nov - 3 Nov
The Weldon Hotel
A stone fireplace with a TV mounted above it, a wooden mantel, and a hanging light fixture.

14. The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace
Freeport
10.0 out of 10, Exceptional, (15 reviews)
"Cottage is just as described. Great place to stay for a few nights to explore the area.Easy walk to Outlets and Restaurants."
United States
Joanne H.
The Outlet Studio, Rustic Comfort w Fireplace
A spacious living room with large windows, a sofa, a chair, and a small table.

15. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (12 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
The price is HK$863
HK$2,592 total
includes taxes & fees
20 Oct - 21 Oct
1 Mi to Maine Street! MCM-Style Home in Brunswick
A modern house with a wooden exterior, a small garden, and a visible window.

16. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (40 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is HK$1,096
HK$3,691 total
includes taxes & fees
20 Oct - 21 Oct
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

17. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (62 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is HK$890
HK$3,049 total
includes taxes & fees
20 Oct - 21 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A house with a wooden staircase leading to a door marked with the number 50.

18. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (107 reviews)
"Very nice place, clean, good location. On-street parking was available. Second floor kitchen & bath, so not for those with issues with stairs, but fine for us. Would stay again!"
United States
Gary
The price is HK$890
HK$2,116 total
includes taxes & fees
3 Nov - 4 Nov
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
A beach with a wooden chair and a small building in the background.

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (71 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is HK$1,492
HK$3,568 total
includes taxes & fees
2 Nov - 3 Nov
Arlie`s Digs! - One Block To Willard Beach!
A wooden deck with outdoor seating and string lights.

20. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (74 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is HK$1,589
HK$2,895 total
includes taxes & fees
14 Oct - 15 Oct
Full sized home
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

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

10/10 Excellent
"No complaints - friendly staff and good property for a one night stay!"
Sam 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Find out more about Cliff Island

Search for holiday rentals in Cliff Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Cliff Island using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in Cliff Island while they last

Look no further and take a look at our great range of rental properties in Cliff Island!

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?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This holiday home rental outside of Cliff Island is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 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, or get out into nature at a spot like Little John Island Preserve. In the wider area, you’ll find Sand Beach 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.