Chebeague Island Holiday Rentals

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Check prices for these dates

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

Our top choices for Chebeague Island holiday rentals

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.
The price is HK$780
HK$1,725 total
includes taxes & fees
20 Jan - 21 Jan
Modern style in historic building in downtown Bath
Smart TV

Apartment in Blue Point

Pine Point Beach private, quaint, charming studio.
2.0 star property
10.0 out of 10, Exceptional, (25 reviews)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is HK$686
HK$1,632 total
includes taxes & fees
20 Jan - 21 Jan
Pine Point Beach private, quaint, charming studio.
Living area

Holiday 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.
The price is HK$737
HK$1,575 total
includes taxes & fees
20 Jan - 21 Jan
Escape to Positive Outlook
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.
The price is HK$702
HK$935 total
includes taxes & fees
20 Jan - 21 Jan
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
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.
The price is HK$663
HK$1,972 total
includes taxes & fees
25 Jan - 26 Jan
Brunswick Downtown Sugar Cube next to Bowdoin
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.
The price is HK$1,032
HK$1,872 total
includes taxes & fees
20 Jan - 21 Jan
Dog Friendly, Relaxing Cottage Stay • Steps Away from The 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
The price is HK$643
HK$1,432 total
includes taxes & fees
20 Jan - 21 Jan
Sunny Spot with Private Parking.
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.
The price is HK$491
HK$1,173 total
includes taxes & fees
3 Feb - 4 Feb
Studio Apartment in Freeport
Interior

Holiday 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.
The price is HK$1,209
HK$3,399 total
includes taxes & fees
20 Jan - 21 Jan
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Egyptian cotton sheets, premium bedding, down duvets, 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
Fortland Island Campground
3 bedrooms, WiFi

Holiday Home in West Point

Fantastic Waterfront Views
9.6 out of 10, Exceptional, (14 reviews)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
The price is HK$982
HK$2,088 total
includes taxes & fees
20 Jan - 21 Jan
Fantastic Waterfront Views
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.
The price is HK$649
HK$1,524 total
includes taxes & fees
20 Jan - 21 Jan
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
The price is HK$1,474
HK$2,749 total
includes taxes & fees
27 Jan - 28 Jan
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Interior

Holiday Home in Cape Elizabeth

Entire ideally located home in Cape Elizabeth’s coveted seaside community
10.0 out of 10, Exceptional, (4 reviews)
"The host was welcoming and it was an easy and smooth check in and check out process. Place was a great spot for my friends and I during our stay for a pond hockey tournament."
United States
Kerry W.
The price is HK$1,266
HK$3,037 total
includes taxes & fees
25 Jan - 26 Jan
Entire ideally located home in Cape Elizabeth’s coveted seaside community
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.
The price is HK$1,310
HK$2,303 total
includes taxes & fees
20 Jan - 21 Jan
Modern, Luxurious, Cabin in the Woods - 17
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 traveller
The price is HK$1,084
HK$5,580 total
includes taxes & fees
16 Feb - 17 Feb
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.
The price is HK$780
HK$1,691 total
includes taxes & fees
20 Jan - 21 Jan
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Property grounds

Holiday Home in Georgetown

Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi
2.0 star property
The price is HK$1,162
HK$2,418 total
includes taxes & fees
20 Jan - 21 Jan
Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi
Fridge, microwave, oven, stovetop

Apartment in Brunswick

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
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 HK$1,053
HK$2,728 total
includes taxes & fees
20 Jan - 21 Jan
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Terrace/patio

Holiday Home in Harpswell

Full sized home
9.8 out of 10, Exceptional, (50 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is HK$1,403
HK$2,592 total
includes taxes & fees
26 Jan - 27 Jan
Full sized home
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

Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

10/10 Excellent
"Super friendly staff!!! Felt genuinely welcomed. Clean room. Quiet. "
Heidi 1-night trip
Posted 1 day ago
Hyatt Place Portland Downtown - Old Port Square

Find out more about Chebeague Island

Search for holiday rentals in Chebeague Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Chebeague Island using one of the methods below:

  • View our selection of featured holiday rentals in Chebeague Island
  • Use the map to find apartments and other holiday homes in the Chebeague Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chebeague Island while they last

Look no further and take a look at our great range of rental properties in Chebeague Island!

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?

Oceanfront Cabin-Castle in Maine Woods: This holiday home rental outside of Chebeague Island is located by the ocean, and has a fireplace, a selection of games and a BBQ 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 that you can cook with friends or family.

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 Sand Beach 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.