Lodging Image

Chebeague Island Holiday 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 holiday rentals

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is AU$895
includes taxes & fees
17 June - 18 June
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

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, (72 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
The price is AU$461
includes taxes & fees
18 June - 19 June
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Adorable 1 bedroom cabin only 50 ft from beach#1

Adorable 1 bedroom cabin only 50 ft from beach#1
Old Orchard Beach
10.0 out of 10, Exceptional, (5 reviews)
"It was the perfect little place to stay for our anniversary!"
United States
Haley W.
The price is AU$543
includes taxes & fees
17 June - 18 June
Adorable 1 bedroom cabin only 50 ft from beach#1

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (31 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
The price is AU$393
includes taxes & fees
28 June - 29 June
Pine Point Beach private, quaint, charming studio.

Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (103 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is AU$649
includes taxes & fees
28 June - 29 June
Ocean View East End Studio in a Historic Victorian

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 AU$514
includes taxes & fees
17 June - 18 June
Camp Forever cottage

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, (152 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 AU$217
includes taxes & fees
17 June - 18 June
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

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 AU$1,042
includes taxes & fees
18 June - 19 June
Award Winning Luxury Carriage House a short stroll from town!

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 AU$549
includes taxes & fees
17 June - 18 June
Modern, Luxurious Cabin in the Woods - 03

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 AU$489
includes taxes & fees
16 July - 17 July
1 Mi to Maine Street! Mcm-style Home in Brunswick

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (61 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 AU$663
includes taxes & fees
20 June - 21 June
Centerview cottage

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (3 reviews)
"Spacious, clean, and in the perfect location in Old Port."
United States
Celine
The price is AU$1,008
includes taxes & fees
17 June - 18 June
Evalina Hotel

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is AU$795
includes taxes & fees
21 June - 22 June
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

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 AU$352
includes taxes & fees
20 June - 21 June
Mid Coast Getaway w/ water views

The Links Lodge - Modern Golf and Beach Retreat

The Links Lodge - Modern Golf and Beach Retreat
Old Orchard Beach
10.0 out of 10, Exceptional, (10 reviews)
"Great home for family!"
United States
Christie B.
The price is AU$1,312
includes taxes & fees
17 June - 18 June
The Links Lodge - Modern Golf and Beach Retreat

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (10 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is AU$1,249
includes taxes & fees
28 June - 29 June
Willard Square Family Home

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 AU$584
includes taxes & fees
18 June - 19 June
Fortland Island Campground

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 AU$656
includes taxes & fees
21 June - 22 June
Large, luxurious geodesic dome - 04

Captain's 2BR Apt. Best value, Near everything, large yard, treehouse. No fees.

Captain's 2BR Apt. Best value, Near everything, large yard, treehouse. No fees.
Bath
8.8 out of 10, Excellent, (11 reviews)
"Clean rooms. Quiet location walkable to much of downtown Bath "
United States
randy k.
The price is AU$359
includes taxes & fees
17 June - 18 June
Captain's 2BR Apt. Best value, Near everything, large yard, treehouse. No fees.

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 AU$497
includes taxes & fees
30 June - 1 July
Downtown Brunswick New Look Old Charm Next to Bowdoin
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

Everything you need to know about Chebeague Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chebeague Island holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chebeague Island holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chebeague Island holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chebeague Island holiday rentals we have selected for you start as low as AU$209 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chebeague Island rentals

At Expedia, we put the best Chebeague Island holiday 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 holiday.

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 holiday rentals in Chebeague Island?

Yes, there are holiday rentals close to the most popular sights in Chebeague Island, or you can select a more secluded option if you're looking for a relaxing stay. Chebeague Island is known for its shopping and restaurants.

What are some of the best holiday rentals that Chebeague Island has to offer?

Modern, Spacious Guest Suite Near the Ocean: This holiday home rental outside of Chebeague Island is located on the beach, and has a patio, a garden and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and an electric kettle. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Chebeague Island?

Expedia has 3 holiday 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 wider area.

What are holiday rentals like in Chebeague Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chebeague Island. Holiday rentals offer amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family trips.