Chebeague Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chebeague Island vacation rentals

Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!

Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!
Bath
8.6 out of 10, Excellent, (10 reviews)
"Clean rooms. Quiet location walkable to much of downtown Bath "
United States
randy k.
The price is CA $254
CA $315 total
includes taxes & fees
May 13 - May 14
Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Lovely location "
United States
Michelle S.
The price is CA $386
CA $763 total
includes taxes & fees
May 18 - May 19
Mere Point Sunrise Views at Eastern Shore!

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (59 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is CA $403
CA $653 total
includes taxes & fees
May 13 - May 14
Centerview cottage

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is CA $259
CA $465 total
includes taxes & fees
May 13 - May 14
Camp Forever cottage

Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
Bath
10.0 out of 10, Exceptional, (9 reviews)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is CA $581
CA $893 total
includes taxes & fees
May 13 - May 14
Award Winning Luxury Carriage House a short stroll from town!

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
The price is CA $259
CA $459 total
includes taxes & fees
May 17 - May 18
Large, luxurious geodesic dome - 04

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is CA $523
CA $570 total
includes taxes & fees
Jun 11 - Jun 12
Fortland Island Campground

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (1 review)
"Beautiful new boutique hotel in Portland! Easy access to the Old Port and everything Portland has to offer. Very quiet, clean and well appointed rooms. The kitchen makes all the difference, even for a short stay! We loved our visit so much that we've booked a second trip!"
United States
Allison
The price is CA $259
CA $488 total
includes taxes & fees
May 17 - May 18
Evalina Hotel

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is CA $251
CA $443 total
includes taxes & fees
May 14 - May 15
Fantastic Waterfront Views

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (29 reviews)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is CA $222
CA $411 total
includes taxes & fees
May 13 - May 14
Pine Point Beach private, quaint, charming studio.

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (64 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is CA $269
CA $563 total
includes taxes & fees
May 13 - May 14
Arlie`s Digs! - One Block To Willard Beach!

Modern Getaway by the Sea

Modern Getaway by the Sea
Ligonia
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our girls weekend catching up and relaxing in this lovely space, with plenty of room and everything we needed! Host was very responsive. Would definitely stay again!"
United States
Kelley F.
The price is CA $445
CA $740 total
includes taxes & fees
May 13 - May 14
Modern Getaway by the Sea

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, (73 reviews)
"Had a really nice stay. "
United States
John F.
The price is CA $1,151
CA $1,688 total
includes taxes & fees
May 13 - May 14
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (5 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is CA $172
CA $332 total
includes taxes & fees
May 18 - May 19
Mid Coast Getaway w/ water views

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (174 reviews)
"Very cute and comfy. We would definitely stay here again. "
United States
Marie s.
The price is CA $447
CA $693 total
includes taxes & fees
Jun 1 - Jun 2
Glorious getaway on Portland's Eastern Promenade.

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is CA $308
CA $543 total
includes taxes & fees
May 14 - May 15
Full sized home

Vacation Creation Downtown Brunswick 2King Beds

Vacation Creation Downtown Brunswick 2King Beds
Brunswick
9.6 out of 10, Exceptional, (19 reviews)
"Stayed here while visiting Bowdoin. Great place!"
United States
Deborah B.
The price is CA $212
CA $543 total
includes taxes & fees
May 13 - May 14
Vacation Creation Downtown Brunswick 2King Beds

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (41 reviews)
"Great home, great location, very accommodating, clear communication."
United States
Kristi H.
The price is CA $324
CA $589 total
includes taxes & fees
May 13 - May 14
Modern & Sunny House Steps from the Promenade. Private Parking!

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (149 reviews)
"Such a fabulous stay. The space was bright, clean, and comfortable, and the special touches made it feel even more welcoming. It was larger than expected, and we loved having a mini fridge and coffee machine, perfect for slow mornings or a little wine and cheese at the end of the day. We’d return in a heartbeat."
Canada
Coral
The price is CA $123
CA $164 total
includes taxes & fees
May 18 - May 19
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (95 reviews)
"Cozy and clean great location "
United States
Michele F.
The Globe House on Munjoy Hill - Walk to Breweries
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chebeague Island Hotel Reviews

Find out more about Chebeague Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chebeague Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Cute House -2 Blocks from Beach: This vacation home rental near Chebeague Island offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

How many vacation rentals are there in Chebeague Island?

Expedia has 3 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 Casco Bay. 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.