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Casco Bay Islands Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 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.
$342 nightly
The price is $343
Nov 16 - Nov 17
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, (131 reviews)
"It was so spacious, kitchen area was well kept and they have QR codes to help travels understand how to use certain things"
United States
Branden
$264 nightly
The price is $281
Nov 30 - Dec 1
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, (19 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
$361 nightly
The price is $393
Dec 7 - Dec 8
Total with taxes and fees
Evalina Hotel
A spacious living room with a large window overlooking a lake, a flat-screen TV mounted on the wall, and a round wooden coffee table.

4. Casco Bay Oceanfront Retreat by Everrow

Casco Bay Oceanfront Retreat by Everrow
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"The house was amazing. We would recommend this property to anyone. The view, stars at night and accessibility to where we wanted to visit, was perfect."
United States
Vanessa K.
$679 nightly
The price is $740
Nov 10 - Nov 11
Total with taxes and fees
Casco Bay Oceanfront Retreat by Everrow
A cabin with two chairs facing a fire pit, surrounded by trees.

5. Cabin w/ bath + kitchenette | Hot tub add-on - 03

Cabin w/ bath + kitchenette | Hot tub add-on - 03
Freeport
9.8 out of 10, Exceptional, (10 reviews)
"A lovely glamping facility with several different types of structure in a quiet, wooded area just a couple miles from downtown Freeport. They've built a beautiful spa with sauna, cold plunge, hot tub, and soaking pool, the unit we stayed in was bright and airy, had an outdoor fire pit. We stayed three nights, will definitely stop here again!"
United States
Kirt v.
$225 nightly
The price is $245
Nov 10 - Nov 11
Total with taxes and fees
Cabin w/ bath + kitchenette | Hot tub add-on - 03
A wooden deck with outdoor seating and string lights.

6. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (80 reviews)
"Wonderful stay!"
United States
Erika T.
$306 nightly
The price is $334
Nov 30 - Dec 1
Total with taxes and fees
Full sized home
A beach with a wooden chair and a small building in the background.

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (73 reviews)
"Great stay!"
United States
Jason M.
$375 nightly
The price is $409
Nov 30 - Dec 1
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

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, (85 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
$947 nightly
The price is $1,032
Nov 12 - Nov 13
Total with taxes and fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A brick wall with a logo and the text 'THE SEND BREWING CO.'

9. Sunny Spot with Private Parking

Sunny Spot with Private Parking
Knightville
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
$183 nightly
The price is $200
Nov 10 - Nov 11
Total with taxes and fees
Sunny Spot with Private Parking
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

10. 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.
$340 nightly
The price is $341
Nov 10 - Nov 11
Total with taxes and fees
Orchid Harbor, Bailey Island 3BR
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

11. 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)
"Everything you need, very clean, close to the water and easily walkable to many things. Would definitely stay again!"
United States
Ryan B.
$194 nightly
The price is $211
Nov 10 - Nov 11
Total with taxes and fees
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A beach with clear water, people swimming, and houses in the background.

12. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard By the Sea - 30 ft to the beach- 2nd floor
Willard
10.0 out of 10, Exceptional, (16 reviews)
"Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach."
United States
Gerald B.
$387 nightly
The price is $406
Nov 16 - Nov 17
Total with taxes and fees
Willard By the Sea - 30 ft to the beach- 2nd floor
A backyard with a wooden deck, a small staircase, and a wooden fence.

13. Great suburban location close to town!

Great suburban location close to town!
Deering Center
9.4 out of 10, Exceptional, (6 reviews)
"We were staying here for the sake of being able to see a show at Good Theater. The theater itself ended up being within walking distance, and same for a few different places to eat! This worked out great for our plans :)"
United States
Kaley
$76 nightly
The price is $77
Nov 11 - Nov 12
Total with taxes and fees
Great suburban location close to town!
A two-story house with a covered porch, a garage, and a front yard with potted plants.

14. 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, (176 reviews)
"This is a really lovely place to stay. Clean and very comfortable with lovely hosts."
United Kingdom
Lucinda
$105 nightly
The price is $114
Dec 1 - Dec 2
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
A brick wall with a logo and the text 'THE SEND BREWING CO.'

15. Peaceful & minutes from Old Port w/private parking

Peaceful & minutes from Old Port w/private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
$217 nightly
The price is $237
Nov 10 - Nov 11
Total with taxes and fees
Peaceful & minutes from Old Port w/private parking
A geodesic dome structure in a forest setting with a visible interior space.

16. Modern dome w/ full bath | Hot tub add-on - 04

Modern dome w/ full bath | Hot tub add-on - 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.
$263 nightly
The price is $287
Nov 10 - Nov 11
Total with taxes and fees
Modern dome w/ full bath | Hot tub add-on - 04
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

17. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (17 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
$743 nightly
The price is $747
Nov 22 - Nov 23
Total with taxes and fees
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

18. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
7.8 out of 10, Good, (18 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.
$78 nightly
The price is $79
Nov 10 - Nov 11
Total with taxes and fees
Portland 1-bedroom with enclosed porch & parking
A gray house with a black front door, white trim, and a number 70 sign.

19. Vintage Maine & Modern Convenience in Portlands Exclusive East End

Vintage Maine & Modern Convenience in Portlands Exclusive East End
Munjoy Hill
9.8 out of 10, Exceptional, (64 reviews)
"The apartment is very comfortable with everything we needed We loved the quiet neighborhood and the location was really great within walking distance to both the beach area and downtown shops & restaurants."
United States
maureen
$419 nightly
The price is $457
Nov 22 - Nov 23
Total with taxes and fees
Vintage Maine & Modern Convenience in Portlands Exclusive East End
A modern kitchen with a central island, stainless steel appliances, and contemporary artwork.

20. A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
Munjoy Hill
10.0 out of 10, Exceptional, (11 reviews)
"Great spot. Roomy. Close to shops and ferries. It had everything we needed to see Portland."
United States
Benton M.
$328 nightly
The price is $357
Nov 10 - Nov 11
Total with taxes and fees
A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
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

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"It was a wonderful and best hotel bed ever"
Cevin 1-night trip
Posted less than an hour ago
Portland Harbor Hotel

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 $117 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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