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Casco Bay Islands Vacation Rentals

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Check prices for these dates

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

Our top choices for Casco Bay Islands vacation rentals

A covered porch with a view of a lake and trees.

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.
$469 nightly
The price is $474
Oct 25 - Oct 26
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

2. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (126 reviews)
"Really nice room and location"
United States
Victoria
$289 nightly
The price is $308
Nov 2 - Nov 3
Total with taxes and fees
The Weldon Hotel
A multi-story building with a stone facade, large windows, and a corner entrance.

3. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (15 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
$420 nightly
The price is $458
Nov 11 - Nov 12
Total with taxes and fees
Evalina Hotel
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

4. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"All we could say was wow! Words cannot express the view from this house! It looked like a picture! Beautiful view, fully loaded kitchen, spacious, comfortable beds, everything was perfect. I have the worst cell service and I couldn’t get the app to work but David answered my call right away and helped us get in. I’d highly recommend this property and we can’t wait to come back!"
United States
Michael L.
$826 nightly
The price is $900
Nov 4 - Nov 5
Total with taxes and fees
Three bedroom in United States of America, Freeport
A beach with a wooden chair and a small building in the background.

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, (71 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
$475 nightly
The price is $518
Nov 9 - Nov 10
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
A cabin with two chairs facing a fire pit, surrounded by trees.

6. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
9.8 out of 10, Exceptional, (10 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
$363 nightly
The price is $395
Oct 28 - Oct 29
Total with taxes and fees
Modern cabin w/ full bath & kitchenette - 03
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

7. 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, (82 reviews)
"Very nice houseLots of roomKitchen well appointed"
United States
george f.
$1,020 nightly
The price is $1,111
Oct 19 - Oct 20
Total with taxes and fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A wooden deck with outdoor seating and string lights.

8. 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.
$339 nightly
The price is $369
Oct 27 - Oct 28
Total with taxes and fees
Full sized home
A street lined with buildings, one with a red door and a sign that reads "MINATO".

9. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (189 reviews)
"The property is well equipped for a long weekend. Parking was convenient. The location offered a quiet place to stay just minutes from Portland’s bustling commercial corridors. Will definitely look to book again on our next visit."
United States
William
$406 nightly
The price is $443
Oct 18 - Oct 19
Total with taxes and fees
Glorious getaway on Portland's Eastern Promenade.
Exterior

10. 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, (114 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.
$426 nightly
The price is $464
Oct 18 - Oct 19
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian
A deck with wicker furniture and a view of the water.

11. 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, (33 reviews)
"Truly wonderful view. Lovely apartment. Nice walks along the shore. Nice Munjoy Hill neighborhood."
United States
M Therese F.
Portland’s Best Ocean Views from a 40-Foot Private Deck
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

12. 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.
$211 nightly
The price is $230
Nov 1 - Nov 2
Total with taxes and fees
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A geodesic dome structure in a forest setting with a visible interior space.

13. 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.
$395 nightly
The price is $430
Oct 21 - Oct 22
Total with taxes and fees
Modern dome w/ full bath + spa access - 04
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

14. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (37 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.
$298 nightly
The price is $325
Oct 18 - Oct 19
Total with taxes and fees
Sunny Spot with Private Parking.
A two-story house with a covered porch, a garage, and a front yard with potted plants.

15. 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
$115 nightly
The price is $125
Nov 3 - Nov 4
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
A street lined with buildings, one with a red door and a sign that reads "MINATO".

16. 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
$265 nightly
The price is $289
Oct 26 - Oct 27
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
A black console table with a mirror above it, a lamp, and a potted plant beside it.

17. 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.
$306 nightly
The price is $334
Nov 1 - Nov 2
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
A building with a brick facade, large windows, and a covered outdoor seating area.

18. Spacious 3 BR in Portland's Libbytown!

Spacious 3 BR in Portland's Libbytown!
Portland
9.4 out of 10, Exceptional, (62 reviews)
"Nice host, great location & property."
United States
Brittney C.
$450 nightly
The price is $491
Oct 15 - Oct 16
Total with taxes and fees
Spacious 3 BR in Portland's Libbytown!
A wooden deck with a view of a lake, surrounded by trees and shrubs.

19. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (74 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
$437 nightly
The price is $476
Oct 15 - Oct 16
Total with taxes and fees
Centerview cottage
A storefront with the sign "OYSTERS" and a "RAW BAR" sign above the entrance.

20. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (47 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
$467 nightly
The price is $509
Nov 1 - Nov 2
Total with taxes and fees
Modern & Sunny House Steps from the Promenade.
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

8/10 Good
"Breakfast was very good. Free parking. But no elevator -- and steep stairs."
Peter 1-night trip
Posted 2 hours ago
Inn at St John Portland In-Town

Find out more about Casco Bay Islands

Everything you need to know about Casco Bay Islands 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 Casco Bay Islands 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 Casco Bay Islands vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Casco Bay Islands vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Casco Bay Islands. 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 Casco Bay Islands 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 $147 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 Casco Bay Islands rentals

At Expedia, we put the best Casco Bay Islands 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 Casco Bay Islands 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 Casco Bay Islands 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 Casco Bay Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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