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Casco Bay Islands Vacation Rentals

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Our top choices for Casco Bay Islands vacation rentals

1. 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 CA $223
CA $579 total
includes taxes & fees
Oct 5 - Oct 6
Mere Point Sunrise Views at Eastern Shore!

2. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (122 reviews)
"Really nice room and location"
United States
Victoria
The price is CA $493
CA $643 total
includes taxes & fees
Oct 25 - Oct 26
The Weldon Hotel

3. 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, (113 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
The price is CA $425
CA $657 total
includes taxes & fees
Oct 19 - Oct 20
Ocean View East End Studio in a Historic Victorian

4. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (149 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is CA $251
CA $406 total
includes taxes & fees
Oct 20 - Oct 21
Adorable Portland getaway on the Eastern Promenade

5. 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.
The price is CA $295
CA $671 total
includes taxes & fees
Oct 26 - Oct 27
Arlie`s Digs! - One Block To Willard Beach!

6. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (13 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is CA $707
CA $984 total
includes taxes & fees
Oct 28 - Oct 29
Evalina Hotel

7. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (185 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is CA $358
CA $577 total
includes taxes & fees
Oct 1 - Oct 2
Glorious getaway on Portland's Eastern Promenade.

8. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (29 reviews)
"Loved this spot and would stay again. Had everything you needed and a great location. Cute little attic spot but nice and cool."
United States
Emily N.
The price is CA $209
CA $359 total
includes taxes & fees
Oct 31 - Nov 1
Charming Studio apartment with WiFi, AC in welcoming Portland

9. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is CA $350
CA $564 total
includes taxes & fees
Oct 5 - Oct 6
Peaceful & minutes from the Old Port with private parking

10. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (44 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is CA $488
CA $794 total
includes taxes & fees
Oct 5 - Oct 6
Modern & Sunny House Steps from the Promenade.

11. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (71 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is CA $287
CA $520 total
includes taxes & fees
Oct 5 - Oct 6
Full sized home

12. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (34 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
The price is CA $279
CA $459 total
includes taxes & fees
Oct 5 - Oct 6
Sunny Spot with Private Parking.

13. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
9.2 out of 10, Wonderful, (19 reviews)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is CA $204
CA $253 total
includes taxes & fees
Oct 4 - Oct 5
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

14. Spacious 3 BR in Portland's Libbytown!

Spacious 3 BR in Portland's Libbytown!
Portland
9.4 out of 10, Exceptional, (62 reviews)
"Very clean and has a lot of amenities"
United States
Philip
Spacious 3 BR in Portland's Libbytown!

15. 2 Bedroom Apartment on Top Floor in Portland's West End

2 Bedroom Apartment on Top Floor in Portland's West End
West End
10.0 out of 10, Exceptional, (88 reviews)
"The rooftop deck makes the climb worth it. Everything was clean neat and organized. Great beds. Communication was fast and friendly. Thanks for a great stay. "
United States
TODD H.
The price is CA $353
CA $681 total
includes taxes & fees
Oct 19 - Oct 20
2 Bedroom Apartment on Top Floor in Portland's West End

16. Modern dome w/ full bath + spa access - 04

Modern dome w/ full bath + spa access - 04
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is CA $322
CA $546 total
includes taxes & fees
Oct 1 - Oct 2
Modern dome w/ full bath + spa access - 04

17. 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, (20 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
The price is CA $538
CA $906 total
includes taxes & fees
Oct 29 - Oct 30
4br2ba House parking A Peaceful Oasis on Munjoy Hill

18. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (8 reviews)
"Excellent in every way."
United States
Robert B.
The price is CA $221
CA $478 total
includes taxes & fees
Oct 27 - Oct 28
Willard Beach–Apartment Near Portland & Parks

19. Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (44 reviews)
"Great vacation rental. Convenient to all we wanted to do in the area. Very clean and very livable property!"
United States
Thomas M.
The price is CA $269
CA $474 total
includes taxes & fees
Oct 1 - Oct 2
Pine Point Beach private, quaint, charming studio.

20. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (11 reviews)
The price is CA $1,027
CA $1,897 total
includes taxes & fees
Oct 12 - Oct 13
Three bedroom in United States of America, Freeport
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 Casco Bay Islands Hotel Reviews

Find out more about Casco Bay Islands

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 Casco Bay Islands. 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.

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