Chebeague Island Vacation Rentals

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Our top choices for Chebeague Island vacation rentals

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3 reviews)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is CA $144
CA $293 total
includes taxes & fees
Mar 9 - Mar 10
Escape to Positive Outlook

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (8 reviews)
"Such a great location! We could easily walk all over the cute downtown."
United States
Keisha C.
The price is CA $137
CA $304 total
includes taxes & fees
Feb 13 - Feb 14
Modern style in historic building in downtown Bath

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (15 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is CA $151
CA $344 total
includes taxes & fees
Feb 9 - Feb 10
Fantastic Waterfront Views

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, (145 reviews)
"Great location to access the area especially route 1 n and s. Room totally met our needs and Susan and Jeff were super nice. This place will make our trip most memorable!"
United States
Don E.
The price is CA $123
CA $164 total
includes taxes & fees
Feb 24 - Feb 25
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.4 out of 10, Very good, (7 reviews)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is CA $116
CA $349 total
includes taxes & fees
Feb 9 - Feb 10
Brunswick Downtown Sugar Cube next to Bowdoin

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (26 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 $121
CA $284 total
includes taxes & fees
Feb 7 - Feb 8
Pine Point Beach private, quaint, charming studio.

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 $248
CA $306 total
includes taxes & fees
Mar 1 - Mar 2
Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Old Orchard Beach
9.8 out of 10, Exceptional, (65 reviews)
"Everything was nice & perfectly described. Great quiet neighborhood loved my stay & so did my Dogs thank you for a lovely stay"
United States
Teresa M.
The price is CA $181
CA $328 total
includes taxes & fees
Feb 10 - Feb 11
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is CA $133
CA $275 total
includes taxes & fees
Feb 8 - Feb 9
Sunny Spot with Private Parking.

Modern, Luxurious, Cabin in the Woods - 17

Modern, Luxurious, Cabin in the Woods - 17
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Awesome camping in a great, quiet campground. The staff is very responsive and all the little details make this place special."
United States
Miranda K.
The price is CA $211
CA $387 total
includes taxes & fees
Feb 8 - Feb 9
Modern, Luxurious, Cabin in the Woods - 17

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.2 out of 10, Wonderful, (15 reviews)
"Simon was very easy to communicate with, the place was clean, the bed was quite comfortable, and we were right by Main Street in Brunswick which made for easy access to food and things to do. Wonderful place to stay!"
United States
Jessica B.
The price is CA $108
CA $336 total
includes taxes & fees
Feb 8 - Feb 9
Little Lincoln beautiful home

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (7 reviews)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is CA $134
CA $291 total
includes taxes & fees
Mar 8 - Mar 9
Peaceful & minutes from the Old Port with private parking

Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (11 reviews)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is CA $154
CA $292 total
includes taxes & fees
Feb 7 - Feb 8
Charming Studio apartment with WiFi, AC in welcoming Portland

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.8 out of 10, Exceptional, (28 reviews)
"This property is newly renovated and is in a great location--right across from the Brunswick Hotel and next to campus. Parking is easy (in the driveway) and the apartment is really spacious!"
United States
Jill C.
The price is CA $164
CA $457 total
includes taxes & fees
Feb 9 - Feb 10
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

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 $157
CA $407 total
includes taxes & fees
Feb 9 - Feb 10
Vacation Creation Downtown Brunswick 2King Beds

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (124 reviews)
"Great location for an our trip; laundry in basement "
United States
maria h.
The price is CA $172
CA $381 total
includes taxes & fees
Feb 9 - Feb 10
City Amenities, Casco Bay Sunrises and Natural Beauty

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (50 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is CA $246
CA $466 total
includes taxes & fees
Feb 9 - Feb 10
Full sized home

Classic New England 1st Floor 3 BR Downtown Brunswick

Classic New England 1st Floor 3 BR Downtown Brunswick
Brunswick
9.6 out of 10, Exceptional, (9 reviews)
"We had a good time in Brunswick.... great location and jumping off point to explore."
United States
Karin S.
The price is CA $164
CA $457 total
includes taxes & fees
Feb 8 - Feb 9
Classic New England 1st Floor 3 BR Downtown Brunswick

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (128 reviews)
"Tidy place in a great location! "
United States
Mary M.
The price is CA $150
CA $277 total
includes taxes & fees
Mar 8 - Mar 9
Adorable Portland getaway on the Eastern Promenade

Warm Coastal Retreat: Your Maine Escape Awaits - 1 block from the beach!

Warm Coastal Retreat: Your Maine Escape Awaits - 1 block from the beach!
Pine Point
9.4 out of 10, Exceptional, (32 reviews)
"Cute place; clean and inviting. Would happily stay again!"
United States
Kelly M.
The price is CA $146
CA $434 total
includes taxes & fees
Feb 8 - Feb 9
Warm Coastal Retreat: Your Maine Escape Awaits - 1 block from the beach!
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

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?

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port: This vacation home rental near Chebeague Island is located on a river and has a fireplace, a furnished patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private yard, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.