Chebeague Island Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Chebeague Island vacation rentals

Living area

Vacation Home in West Point

Escape to Positive Outlook
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.
$192 nightly
The price is $202
Jan 25 - Jan 26
Total with taxes and fees
Escape to Positive Outlook
Interior

Apartment in Bath

Modern style in historic building in downtown 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.
$205 nightly
The price is $223
Jan 23 - Jan 24
Total with taxes and fees
Modern style in historic building in downtown Bath
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

Camping in Portland

Fortland Island Campground
1.0 star property
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
$23,275 nightly
The price is $25,370
Feb 2 - Feb 3
Total with taxes and fees
Fortland Island Campground
Exterior

Apartment in Brunswick

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
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.
$110 nightly
The price is $120
Jan 26 - Jan 27
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Interior

Apartment in Knightville

Sunny Spot with Private Parking.
2.0 star property
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
$183 nightly
The price is $199
Jan 25 - Jan 26
Total with taxes and fees
Sunny Spot with Private Parking.
Smart TV

Apartment in Blue Point

Pine Point Beach private, quaint, charming studio.
2.0 star property
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.
$192 nightly
The price is $209
Jan 23 - Jan 24
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
TV

Apartment in Brunswick

Brunswick Downtown Sugar Cube next to Bowdoin
8.4 out of 10, Very Good, (7 reviews)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
$232 nightly
The price is $253
Jan 25 - Jan 26
Total with taxes and fees
Brunswick Downtown Sugar Cube next to Bowdoin
3 bedrooms, WiFi

Vacation Home in West Point

Fantastic Waterfront Views
9.6 out of 10, Exceptional, (14 reviews)
"it's a beautiful property and the owner was very helpful in our times of need."
United States
ROSEMARY A.
$231 nightly
The price is $243
Jan 26 - Jan 27
Total with taxes and fees
Fantastic Waterfront Views
Interior

Apartment in Freeport

Studio Apartment in Freeport
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"I could not have ask for a better place to stay for my winter holiday trip in Freeport, Maine. This studio apartment went above my expectations. The entire space was much larger than I thought it would be. From the entry downstairs & throughout the entire apartment, it was clean & well-kept. Kitchen is fully equipped, has adequate space for meal prep, and there is plenty of room around the table & kitchen counter for dining. The living room is a welcoming pleasant area, and there is ample space...
United States
Di W.
$137 nightly
The price is $144
Jan 25 - Jan 26
Total with taxes and fees
Studio Apartment in Freeport
Interior

Cottage in Old Orchard Beach

Dog Friendly, Relaxing Cottage Stay • Steps Away from The 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.
$235 nightly
The price is $256
Feb 10 - Feb 11
Total with taxes and fees
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Interior

Vacation Home in Brunswick

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"This house was clean and just as described! Close to campus and downtown. Our host was responsive and very helpful!"
United States
Erin B.
$401 nightly
The price is $437
Jan 25 - Jan 26
Total with taxes and fees
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Outdoor dining

Cabin in Freeport

Modern, Luxurious, Cabin in the Woods - 17
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.
$272 nightly
The price is $296
Jan 25 - Jan 26
Total with taxes and fees
Modern, Luxurious, Cabin in the Woods - 17
Outdoor dining

Apartment in Knightville

Peaceful & minutes from the Old Port with private parking
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.
$195 nightly
The price is $213
Jan 25 - Jan 26
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
Property grounds

Cabin in Georgetown

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
2.0 star property
$340 nightly
The price is $361
Jan 27 - Jan 28
Total with taxes and fees
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Exterior detail

Apartment in Munjoy Hill

Adorable Portland getaway on the Eastern Promenade
9.6 out of 10, Exceptional, (128 reviews)
"Tidy place in a great location! "
United States
Mary M.
$181 nightly
The price is $197
Jan 23 - Jan 24
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
Beach nearby

Cottage in Old Orchard Beach

Cheerful 1 bedroom cottage only 50ft from beach
10.0 out of 10, Exceptional, (2 reviews)
"We loved the area. We loved the cottage feel. We only wished it had bigger fridge and a better cook top. Other then that it was great."
United States
Chris A.
$208 nightly
The price is $227
Jan 25 - Jan 26
Total with taxes and fees
Cheerful 1 bedroom cottage only 50ft from beach
1 bedroom, desk, free WiFi, bed sheets

Apartment in Windham

Spacious Studio Near Sebago Lake
2.0 star property
10.0 out of 10, Exceptional, (4 reviews)
"Host was very welcoming and check in was simple "
United States
Michael C.
$118 nightly
The price is $128
Jan 23 - Jan 24
Total with taxes and fees
Spacious Studio Near Sebago Lake
Beach

Condo in East Deering

City Amenities, Casco Bay Sunrises and Natural Beauty
9.8 out of 10, Exceptional, (124 reviews)
"Great location for an our trip; laundry in basement "
United States
maria h.
$275 nightly
The price is $300
Jan 25 - Jan 26
Total with taxes and fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Fridge, microwave, oven, stovetop

Cabin in Gray

Waterfront Access with Kayaks, Private Deck and a Firepit
2.0 star property
10.0 out of 10, Exceptional, (4 reviews)
" The place was wonderful!! Very peaceful and beautiful!! "
United States
Anonymous traveler
$643 nightly
The price is $708
Feb 16 - Feb 17
Total with taxes and fees
Waterfront Access with Kayaks, Private Deck and a Firepit
Interior

Cottage in Old Orchard Beach

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
8.0 out of 10, Very Good, (24 reviews)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
$198 nightly
The price is $216
Jan 26 - Jan 27
Total with taxes and fees
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
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

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

10/10 Excellent
"The perfect hotel if you’re looking for a cozy place for a quick stopover. The staff was very friendly and welcoming. "
Nicole 1-night trip
Posted 1 day ago
Tru by Hilton Portland Airport Area

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 $124 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.

Explore a world of travel with Expedia

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?

Oceanfront Cabin-Castle in Maine Woods: This vacation home rental near Chebeague Island is located by the ocean and has a fireplace, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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 Sand Beach 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.