Chebeague Island 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 Chebeague Island vacation rentals

A wooden deck with outdoor seating and string lights.

1. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (80 reviews)
"Great house! Enjoyed our stay very much. Comfortable, clean, and many nice extra touches i.e. games, books."
United States
Jill J.
The price is CA $282
CA $492 total
includes taxes & fees
Dec 1 - Dec 2
Full sized home
A cabin with two chairs facing a fire pit, surrounded by trees.

2. 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.
The price is CA $275
CA $445 total
includes taxes & fees
Nov 12 - Nov 13
Cabin w/ bath + kitchenette | Hot tub add-on - 03
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

3. 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.
The price is CA $244
CA $574 total
includes taxes & fees
Nov 16 - Nov 17
Orchid Harbor, Bailey Island 3BR
A geodesic dome structure in a forest setting with a visible interior space.

4. 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.
The price is CA $299
CA $490 total
includes taxes & fees
Nov 12 - Nov 13
Modern dome w/ full bath | Hot tub add-on - 04
A multi-story building with a stone facade, large windows, and a corner entrance.

5. 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
The price is CA $333
CA $575 total
includes taxes & fees
Dec 7 - Dec 8
Evalina Hotel
Living area

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
The price is CA $258
CA $388 total
includes taxes & fees
Dec 2 - Dec 3
The Weldon 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.

7. 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.
The price is CA $523
CA $1,204 total
includes taxes & fees
Nov 16 - Nov 17
Casco Bay Oceanfront Retreat by Everrow
A covered porch with a view of a lake and trees.

8. 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 $175
CA $495 total
includes taxes & fees
Nov 16 - Nov 17
Mere Point Sunrise Views at Eastern Shore!
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

9. 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.
The price is CA $176
CA $295 total
includes taxes & fees
Nov 16 - Nov 17
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A beach with clear water, people swimming, and houses in the background.

10. 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.
The price is CA $213
CA $594 total
includes taxes & fees
Nov 17 - Nov 18
Willard By the Sea - 30 ft to the beach- 2nd floor
A room with two wicker chairs, a potted plant, and a view of a body of water and buildings through large windows with blinds.

11. 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 !"
United States
Anonymous traveller
The price is CA $222
CA $576 total
includes taxes & fees
Nov 12 - Nov 13
2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

12. 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.
The price is CA $96
CA $101 total
includes taxes & fees
Nov 15 - Nov 16
Portland 1-bedroom with enclosed porch & parking
A brick wall with a logo and the text 'THE SEND BREWING CO.'

13. 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.
The price is CA $171
CA $332 total
includes taxes & fees
Nov 15 - Nov 16
Peaceful & minutes from Old Port w/private parking
A backyard with a wooden deck, a small staircase, and a wooden fence.

14. 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
The price is CA $92
CA $110 total
includes taxes & fees
Nov 12 - Nov 13
Great suburban location close to town!
A brick wall with a logo and the text 'THE SEND BREWING CO.'

15. 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.
The price is CA $142
CA $280 total
includes taxes & fees
Nov 15 - Nov 16
Sunny Spot with Private Parking
A cabin with a fire pit and outdoor seating.

16. Modern cabin w/ full bath | Hot tub add-on - 19

Modern cabin w/ full bath | Hot tub add-on - 19
Freeport
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!"
United States
Kim L.
The price is CA $275
CA $445 total
includes taxes & fees
Nov 12 - Nov 13
Modern cabin w/ full bath | Hot tub add-on - 19
A modern kitchen with a central island, stainless steel appliances, and contemporary artwork.

17. 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.
The price is CA $279
CA $498 total
includes taxes & fees
Nov 16 - Nov 17
A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
A modern living room with a wooden dining table, chairs, a TV, and a bookshelf.

18. East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (47 reviews)
"A great place to stay while exploring and visiting Portland! Great communication, easy process, and would definitely stay again if we visit Franklin"
United States
Jordan M.
The price is CA $301
CA $497 total
includes taxes & fees
Nov 22 - Nov 23
East end. Walk to food, beer and downtown fun.
A cabin with a fire pit and outdoor seating.

19. Glamping cabin w/ full bath | Hot tub add-on - 21

Glamping cabin w/ full bath | Hot tub add-on - 21
Freeport
10.0 out of 10, Exceptional, (1 review)
The price is CA $275
CA $445 total
includes taxes & fees
Nov 12 - Nov 13
Glamping cabin w/ full bath | Hot tub add-on - 21
A storefront with the sign 'OYSTERS' and a 'RAW BAR' sign above the entrance. There are outdoor seating areas with tables and chairs.

20. Modern & Sunny East End House.

Modern & Sunny East End House.
Munjoy Hill
10.0 out of 10, Exceptional, (51 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is CA $441
CA $741 total
includes taxes & fees
Nov 12 - Nov 13
Modern & Sunny East End House.
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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Find vacation rentals that suit your style

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Top Chebeague Island Hotel Reviews

A hotel reception area with a wooden reception desk, a colorful abstract wall art, and a view of the outdoor area through a window.
Spark by Hilton Freeport

Spark by Hilton Freeport

Spark by Hilton Freeport
Freeport

10/10 Excellent

Entièrement rénové. Très bonne insonorisation. Simple mais très bien
Canada
Sophie
Reviewed September 30, 2026
Spark by Hilton Freeport

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chebeague Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chebeague Island vacation rentals we have selected for you start as low as CA $83 per night. Entering your travel dates in the search wizard 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.

Frequently Asked Questions

Are there vacation rentals in Chebeague Island?

Yes, we have vacation rentals near popular attractions in Chebeague Island, or you can select a secluded option if you're looking for relaxation. Chebeague Island is known for its shopping and restaurants.

What's the top vacation rental in Chebeague Island?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This vacation home rental near Chebeague Island is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Chebeague Island?

Expedia has 4 vacation rentals for your stay in Chebeague Island.

What can I see and do in Chebeague Island?

Explore the area and family-friendly sights such as Portland Observatory, or get out into nature at a spot like Little John Island Preserve. Wolfe's Neck Woods State Park and Bailey Island Bridge are a couple of places you'll find in the larger area.

What are vacation rentals like in Chebeague Island?

Vacation rentals are private properties you can book for several days or more in Chebeague Island. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a small group gathering.