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Chebeague Island Vacation Rentals

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Our top choices for Chebeague Island vacation rentals

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, (153 reviews)
"The place was lovely, communications with the host were helpful and friendly. Dinner restaurant recommendations were great as well. "
United States
Jane T.
The price is CA $160
CA $206 total
includes taxes & fees
Jul 5 - Jul 6
Large suite/private bath/private entrance on quiet street near Thomas Bay

Captain's Guest Room. Authenticity. Value. Near everything. No fees.

Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Bath
8.2 out of 10, Very good, (22 reviews)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
The price is CA $162
CA $207 total
includes taxes & fees
Jun 29 - Jun 30
Captain's Guest Room. Authenticity. Value. Near everything. No fees.

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is CA $197
CA $442 total
includes taxes & fees
Jul 16 - Jul 17
1 Mi to Maine Street! Mcm-style Home in Brunswick

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.4 out of 10, Exceptional, (6 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is CA $224
CA $403 total
includes taxes & fees
Jul 2 - Jul 3
Mid Coast Getaway w/ water views

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (10 reviews)
"Clean comfortable and right downtown"
United States
stephen e.
The price is CA $167
CA $350 total
includes taxes & fees
Jun 29 - Jun 30
Modern style in historic building in downtown Bath

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 $298
CA $517 total
includes taxes & fees
Jun 27 - Jun 28
Camp Forever cottage

King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
10.0 out of 10, Exceptional, (15 reviews)
"Great location surroundings a little unkept but tis the spring cleanup season. Excellent accommodation and located near town shopping but quiet neighborhood"
United States
Douglas H.
The price is CA $333
CA $592 total
includes taxes & fees
Jul 1 - Jul 2
King Size Sun Rise Midcoast Lovely Stay

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (33 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
The price is CA $204
CA $394 total
includes taxes & fees
Jun 28 - Jun 29
Pine Point Beach private, quaint, charming studio.

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is CA $369
CA $607 total
includes taxes & fees
Jun 29 - Jun 30
Large, luxurious geodesic dome - 04

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is CA $321
CA $526 total
includes taxes & fees
Jun 28 - Jun 29
Modern, Luxurious Cabin in the Woods - 03

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Pine Point
9.6 out of 10, Exceptional, (42 reviews)
"Beautiful, clean place to stay and dogs welcome "
United States
Anonymous traveller
The price is CA $207
CA $524 total
includes taxes & fees
Jul 1 - Jul 2
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Downtown Brunswick New Look Old Charm Next to Bowdoin

Downtown Brunswick New Look Old Charm Next to Bowdoin
Brunswick
9.8 out of 10, Exceptional, (21 reviews)
"We really enjoyed our visit with family and friends and the location was perfect for what we needed. "
United States
Eliza
The price is CA $235
CA $506 total
includes taxes & fees
Jun 30 - Jul 1
Downtown Brunswick New Look Old Charm Next to Bowdoin

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (53 reviews)
"Wonderful stay!"
United States
Erika T.
The price is CA $287
CA $527 total
includes taxes & fees
Jul 1 - Jul 2
Full sized home

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (27 reviews)
The price is CA $365
CA $569 total
includes taxes & fees
Jul 7 - Jul 8
Sunny Spot with Private Parking.

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Apartment was very cute, clean, and just what I was looking for. Jennifer was very accommodating and understanding "
United States
Jolee S.
The price is CA $274
CA $475 total
includes taxes & fees
Jun 29 - Jun 30
Peaceful & minutes from the Old Port with private parking

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (62 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 $419
CA $674 total
includes taxes & fees
Jun 28 - Jun 29
Centerview cottage

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
The price is CA $537
CA $586 total
includes taxes & fees
Jul 21 - Jul 22
Fortland Island Campground

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, (74 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
The price is CA $275
CA $476 total
includes taxes & fees
Jul 1 - Jul 2
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

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, (38 reviews)
"Clean, great location, excellent communication with host, perfectly furnished for our group"
United States
Elizabeth P.
The price is CA $301
CA $524 total
includes taxes & fees
Jun 28 - Jun 29
East end. Walk to food, beer and downtown fun.

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

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.6 out of 10, Exceptional, (33 reviews)
"Wonderful location. It’s right next to Bowdoin. There is a great coffee shop a block away and a grocery store within easy walking distance. The place was spotless. "
United States
Mike S.
The price is CA $348
CA $696 total
includes taxes & fees
Jun 28 - Jun 29
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
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?

Cozy & Quiet Home in Portland Maine. One Bedroom, Private Bathroom “No Kitchen”: This vacation home rental near Chebeague Island is located on the beach and offers a fireplace, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and an electric kettle.

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 Wolfe's Neck Farm. 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.