Chebeague Island Vacation Rentals
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Our top choices for Chebeague Island vacation rentals
1. Portland 1-bedroom with enclosed porch & parking
Portland 1-bedroom with enclosed porch & parkingDeering Center
8.0 out of 10, Very good, (17 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
Cricket C.
$71 nightly
The price is $72
Nov 8 - Nov 9
Total with taxes and fees
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 :)"
Kaley
$77 nightly
The price is $78
Nov 9 - Nov 10
Total with taxes and fees
3. Orchid Harbor, Bailey Island 3BR
Orchid Harbor, Bailey Island 3BRHarpswell
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."
Jane D.
$352 nightly
The price is $354
Nov 10 - Nov 11
Total with taxes and fees
4. Full sized home
Full sized homeHarpswell
9.8 out of 10, Exceptional, (80 reviews)
"Wonderful stay!"
Erika T.
$319 nightly
The price is $348
Nov 30 - Dec 1
Total with taxes and fees
5. 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 "
Michelle S.
$357 nightly
The price is $360
Nov 16 - Nov 17
Total with taxes and fees
6. Cabin w/ bath + kitchenette | Hot tub add-on - 03
Cabin w/ bath + kitchenette | Hot tub add-on - 03Freeport
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!"
Kirt v.
$293 nightly
The price is $319
Nov 6 - Nov 7
Total with taxes and fees
7. Glamping cabin w/ full bath | Hot tub add-on - 21
Glamping cabin w/ full bath | Hot tub add-on - 21Freeport
10.0 out of 10, Exceptional, (1 review)
$305 nightly
The price is $332
Nov 10 - Nov 11
Total with taxes and fees
8. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming PortlandMunjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Had a wonderful stay. Very clean and great location."
Aimee S.
$192 nightly
The price is $209
Nov 8 - Nov 9
Total with taxes and fees
9. Evalina Hotel
Evalina HotelDowntown Portland
10.0 out of 10, Exceptional, (18 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
Rick
$358 nightly
The price is $390
Dec 6 - Dec 7
Total with taxes and fees
10. Mid Coast Getaway w/ water views
Mid Coast Getaway w/ water viewsWest 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!"
Rebecca
$194 nightly
The price is $205
Nov 8 - Nov 9
Total with taxes and fees
11. Studio Apartment near downtown Walkable!
Studio Apartment near downtown Walkable!West Bayside
8.2 out of 10, Very good, (26 reviews)
"Location was convenient to everything and building was super secure."
Rose
$121 nightly
The price is $122
Nov 12 - Nov 13
Total with taxes and fees
12. Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown FreeportFreeport
10.0 out of 10, Exceptional, (12 reviews)
"Our whole family was impressed by this house!"
Gary B.
$594 nightly
The price is $647
Nov 23 - Nov 24
Total with taxes and fees
13. The Weldon Hotel
The Weldon HotelDowntown Portland
9.8 out of 10, Exceptional, (130 reviews)
"Really nice room and location"
Victoria
$263 nightly
The price is $280
Nov 16 - Nov 17
Total with taxes and fees
14. Casco Bay Oceanfront Retreat by Everrow
Casco Bay Oceanfront Retreat by EverrowFreeport
10.0 out of 10, Exceptional, (13 reviews)
"What can I say about my stay; peaceful, beautiful views, and relaxing! Home was clean with modern finishes but super comfortable for my four guests. The downstairs area is very private from the main floor. The yard was a great space where we had our outdoor fire looking up at the stars at night. The deck was perfect for our family lunch and dinners. We took chairs down to the beach area to sit closer to the water which was perfect. It's super close to town, Wolfe's Neck and other amenities....
Lisa E.
$768 nightly
The price is $837
Nov 8 - Nov 9
Total with taxes and fees
15. Willard By the Sea - 30 ft to the beach- 2nd floor
Willard By the Sea - 30 ft to the beach- 2nd floorWillard
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."
Gerald B.
$472 nightly
The price is $495
Nov 17 - Nov 18
Total with taxes and fees
16. Sunny Spot with Private Parking
Sunny Spot with Private ParkingKnightville
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."
Greg Z.
$222 nightly
The price is $244
Nov 6 - Nov 7
Total with taxes and fees
17. Peaceful & minutes from Old Port w/private parking
Peaceful & minutes from Old Port w/private parkingKnightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
Kelly S.
$231 nightly
The price is $254
Nov 7 - Nov 8
Total with taxes and fees
18. Beautiful 1st Floor Apartment & Amazing Shower
Beautiful 1st Floor Apartment & Amazing ShowerParkside
8.6 out of 10, Excellent, (35 reviews)
"This was a clean and good location for our stay. "
Jocelyn R.
$142 nightly
The price is $155
Nov 8 - Nov 9
Total with taxes and fees
19. 2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!
2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!Munjoy Hill
10.0 out of 10, Exceptional, (6 reviews)
"Lovely clean property in a really great location. Walkable to town center! Perfect !"
Anonymous traveler
$378 nightly
The price is $411
Nov 9 - Nov 10
Total with taxes and fees
20. Modern cabin w/ full bath | Hot tub add-on - 19
Modern cabin w/ full bath | Hot tub add-on - 19Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Great place, the Desert of Maine campground. The entire cabin was spotless. Great communication from the host, Doug. So wonderful for pets also. Quiet, clean & perfect. 5 stars. What a wonderful stay! If you are looking for a beautiful and peaceful get away, this is the place for you! You will not be disappointed. Doug is an awesome host!"
Kim L.
$321 nightly
The price is $350
Nov 8 - Nov 9
Total with taxes and fees
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 Chebeague Island Hotel Reviews
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
8/10 Good
Find out more about Chebeague Island
Everything you need to know about Chebeague 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 Chebeague 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 Chebeague Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Chebeague Island vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Chebeague 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 Chebeague 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 $120 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 Chebeague Island rentals
At Expedia, we put the best Chebeague 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 Chebeague 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 Chebeague 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 Chebeague 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.
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