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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)
"This little spot was an ideal getaway for our family’s summer trip to Maine. We very much enjoyed the porch with a view of the water and felt right at home here."
United States
James C.
$346 nightly
The price is $348
Nov 16 - Nov 17
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!
A backyard with a wooden deck, a small staircase, and a wooden fence.

2. 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
$68 nightly
The price is $68
Nov 16 - Nov 17
Total with taxes and fees
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.

3. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
7.8 out of 10, Good, (19 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.
$71 nightly
The price is $72
Nov 15 - Nov 16
Total with taxes and fees
Portland 1-bedroom with enclosed porch & parking
A brick wall with a logo and the text 'THE SEND BREWING CO.'

4. 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.
$181 nightly
The price is $198
Nov 15 - Nov 16
Total with taxes and fees
Sunny Spot with Private Parking
A gym with treadmills, elliptical machines, and exercise balls.

5. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
9.4 out of 10, Exceptional, (23 reviews)
"We really appreciated our stay!"
United States
Anonymous traveler
$102 nightly
The price is $111
Nov 16 - Nov 17
Total with taxes and fees
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

6. 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
$252 nightly
The price is $268
Dec 1 - Dec 2
Total with taxes and fees
The Weldon Hotel
A two-story house with a covered porch, a garage, and a front yard with potted plants.

7. 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
$107 nightly
The price is $117
Nov 22 - Nov 23
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

8. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (27 reviews)
"Location was convenient to everything and building was super secure."
United States
Rose
$121 nightly
The price is $122
Nov 19 - Nov 20
Total with taxes and fees
Studio Apartment near downtown Walkable!
A kitchen with wooden cabinets, a stainless steel sink, and a potted plant.

9. 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.
$126 nightly
The price is $137
Nov 17 - Nov 18
Total with taxes and fees
Bright & Spacious Apartment with Amazing Shower
A multi-story building with a stone facade, large windows, and a corner entrance.

10. 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
$358 nightly
The price is $390
Dec 14 - Dec 15
Total with taxes and fees
Evalina Hotel
A brick wall with a logo and the text 'THE SEND BREWING CO.'

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

Peaceful & minutes from Old Port w/private parking
Knightville
9.8 out of 10, Exceptional, (14 reviews)
"Cute, convenient spot!"
United States
Kelly S.
$215 nightly
The price is $235
Nov 15 - Nov 16
Total with taxes and fees
Peaceful & minutes from Old Port w/private parking
A living room with a sofa, armchairs, a coffee table, and a potted plant.

12. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (35 reviews)
"Good price, decent location, clean, and affordable"
United States
Chloe C.
$128 nightly
The price is $139
Nov 18 - Nov 19
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
A cabin with two chairs facing a fire pit, surrounded by trees.

13. 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.
$235 nightly
The price is $256
Nov 15 - Nov 16
Total with taxes and fees
Cabin w/ bath + kitchenette | Hot tub add-on - 03
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

14. 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
$190 nightly
The price is $200
Nov 16 - Nov 17
Total with taxes and fees
Mid Coast Getaway w/ water views
A modern kitchen with white cabinets, a wooden dining table, and a vase with green leaves.

15. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (19 reviews)
"The place was clean, bright, and exactly as shown in the pictures. There were fresh towels (4), toiletries, dishsoap/dishwasher tablets, and an in window AC. The table and bed are both lovely and roomy for two people. Plenty of places to plug in devices. The Seadog brewery was walking distance and would recommend for dinner and a pint. Also enjoyed Dutchman's bagels and Baked on Main (marginally longer walk). We were really happy with our stay!"
United States
Stefanie M.
$210 nightly
The price is $212
Nov 15 - Nov 16
Total with taxes and fees
King Size Sun Rise Midcoast Lovely Stay
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

16. 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.
$393 nightly
The price is $395
Dec 13 - Dec 14
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.

17. 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.
$192 nightly
The price is $209
Nov 16 - Nov 17
Total with taxes and fees
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A spacious kitchen with a large island, bar stools, and a dining area with a sofa.

18. King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer

King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
Topsham
9.6 out of 10, Exceptional, (8 reviews)
"Perfect place and location for visiting Bowdoin."
United States
Kristen S.
$237 nightly
The price is $239
Nov 16 - Nov 17
Total with taxes and fees
King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

19. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
$306 nightly
The price is $333
Nov 16 - Nov 17
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
A beach with clear water, people swimming, and houses in the background.

20. 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.
$389 nightly
The price is $409
Nov 17 - Nov 18
Total with taxes and fees
Willard By the Sea - 30 ft to the beach- 2nd floor
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

The Westin Portland Harborview

The Westin Portland Harborview

10/10 Excellent
"Great place"
Loretta 1-night trip
Posted 4 hours ago
The Westin Portland Harborview

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 $111 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

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