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Cliff Island Vacation Rentals

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Our top choices for Cliff Island vacation rentals

1. 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
$369 nightly
The price is $403
Sep 24 - Sep 25
Total with taxes and fees
Fortland Island Campground

2. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (117 reviews)
"Really nice room and location"
United States
Victoria
$384 nightly
The price is $418
Sep 8 - Sep 9
Total with taxes and fees
The Weldon Hotel

3. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (11 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
$630 nightly
The price is $687
Sep 8 - Sep 9
Total with taxes and fees
Evalina Hotel

4. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
10.0 out of 10, Exceptional, (111 reviews)
"Lovely home in a beautiful location and Dan is a fantastic host. Ask him about his hot sauce!"
United States
Elliott H.
$426 nightly
The price is $464
Sep 7 - Sep 8
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian

5. 'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
$579 nightly
The price is $614
Sep 30 - Oct 1
Total with taxes and fees
'osprey Cottage' South Freeport Home on Casco Bay!

6. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (183 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
$427 nightly
The price is $465
Sep 9 - Sep 10
Total with taxes and fees
Glorious getaway on Portland's Eastern Promenade.

7. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (146 reviews)
"Owner was so accommodating!"
United States
Kiernan
Adorable Portland getaway on the Eastern Promenade

8. 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, (80 reviews)
"Everything was very well stocked!"
United States
Sally O.
$1,181 nightly
The price is $1,287
Sep 10 - Sep 11
Total with taxes and fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

9. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (68 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
$340 nightly
The price is $370
Oct 7 - Oct 8
Total with taxes and fees
Full sized home

10. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

4br2ba House parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (18 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
$543 nightly
The price is $592
Oct 6 - Oct 7
Total with taxes and fees
4br2ba House parking A Peaceful Oasis on Munjoy Hill

11. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (43 reviews)
"Overall amazing experience! Property is beautifully maintained. Perfectly located, within walking distance from bakeries, pubs, and restraunts. Host was responsive and helpful."
United States
Jacqui B.
$469 nightly
The price is $512
Sep 8 - Sep 9
Total with taxes and fees
Modern & Sunny House Steps from the Promenade.

12. 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, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
$522 nightly
The price is $569
Sep 15 - Sep 16
Total with taxes and fees
The Globe House on Munjoy Hill - Walk to Breweries

13. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (8 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
$265 nightly
The price is $282
Sep 13 - Sep 14
Total with taxes and fees
Mid Coast Getaway w/ water views

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
$815 nightly
The price is $888
Oct 1 - Oct 2
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!

15. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (131 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
$394 nightly
The price is $429
Sep 15 - Sep 16
Total with taxes and fees
City Amenities, Casco Bay Sunrises and Natural Beauty

16. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (65 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
$333 nightly
The price is $363
Sep 10 - Sep 11
Total with taxes and fees
Camp Forever cottage

17. Island View House BnB Self Check-In # 4 / Free Off-Street Parking

Island View House BnB Self Check-In # 4 / Free Off-Street Parking
Munjoy Hill
9.6 out of 10, Exceptional, (17 reviews)
"Loved the place! Very eclectic. Easy walk to downtown. Definitely will be back!"
United States
Cameron H.
$494 nightly
The price is $538
Sep 7 - Sep 8
Total with taxes and fees
Island View House BnB Self Check-In # 4 / Free Off-Street Parking

18. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (70 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
$415 nightly
The price is $452
Sep 10 - Sep 11
Total with taxes and fees
Centerview cottage

19. 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, (166 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
$152 nightly
The price is $166
Sep 15 - Sep 16
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay

20. East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (42 reviews)
"Exactly as described and in one of the loveliest parts of Portland! Communication with owner was smooth and seamless. Perfect place to get to multiple places of interest in this charming city."
United States
Emily W.
$345 nightly
The price is $368
Sep 8 - Sep 9
Total with taxes and fees
East end. Walk to food, beer and downtown fun.
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cliff Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cliff Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cliff Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $178 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cliff Island rentals

At Expedia, we put the best Cliff Island vacation 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 vacation.

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 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?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This vacation home rental outside of Cliff Island is located on the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 Sand Beach. In the larger area, you’ll find Fifth Maine Museum and Casco Bay.

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.