Chebeague Island Holiday Rentals

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Our top choices for Chebeague Island holiday rentals

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is NZ$346
includes taxes & fees
11 Jan - 12 Jan
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)
"Such a great location! We could easily walk all over the cute downtown."
United States
Keisha C.
The price is NZ$383
includes taxes & fees
8 Jan - 9 Jan
Modern style in historic building in downtown Bath

Near Reid State Park Beach+FirePit+Pond+Heat/AC+Fast WiFi+S'mores

Near Reid State Park Beach+FirePit+Pond+Heat/AC+Fast WiFi+S'mores
2.0 star property
Georgetown
The price is NZ$531
includes taxes & fees
8 Jan - 9 Jan
Near Reid State Park Beach+FirePit+Pond+Heat/AC+Fast WiFi+S'mores

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)
"Nice, clean, cosy, conveniently located and easy enough to find. Great communication with host, comfortable beds and plenty of hot water. very responsive and would definitely consider using again. "
United States
A M.
The price is NZ$336
includes taxes & fees
8 Jan - 9 Jan
Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (14)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
The price is NZ$463
includes taxes & fees
8 Jan - 9 Jan
Fantastic Waterfront Views

The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace
Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable, clean, with a spacious bathroom and within walking distance of downtown Freeport and Bow Street Market"
United States
Deanna S.
The Outlet Studio, Rustic Comfort w Fireplace

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)
"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 NZ$207
includes taxes & fees
18 Jan - 19 Jan
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Modern, Luxurious, Cabin in the Woods - 17

Modern, Luxurious, Cabin in the Woods - 17
Freeport
10.0 out of 10, Exceptional, (3)
"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 NZ$511
includes taxes & fees
11 Jan - 12 Jan
Modern, Luxurious, Cabin in the Woods - 17

Studio Apartment in Freeport

Studio Apartment in Freeport
2.0 star property
Freeport
10.0 out of 10, Exceptional, (1)
"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 NZ$262
includes taxes & fees
1 Feb - 2 Feb
Studio Apartment in Freeport

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
2.0 star property
Knightville
9.8 out of 10, Exceptional, (25)
"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 NZ$347
includes taxes & fees
14 Jan - 15 Jan
Sunny Spot with Private Parking.

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.4 out of 10, Very good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is NZ$454
includes taxes & fees
11 Jan - 12 Jan
Brunswick Downtown Sugar Cube next to Bowdoin

Private Sauna+Near Beach+FirePit+Forest View+Pond

Private Sauna+Near Beach+FirePit+Forest View+Pond
2.0 star property
Georgetown
The price is NZ$637
includes taxes & fees
20 Jan - 21 Jan
Private Sauna+Near Beach+FirePit+Forest View+Pond

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (91)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is NZ$464
includes taxes & fees
16 Jan - 17 Jan
The Weldon Hotel

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
2.0 star property
Blue Point
10.0 out of 10, Exceptional, (25)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is NZ$354
includes taxes & fees
8 Jan - 9 Jan
Pine Point Beach private, quaint, charming studio.

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)
"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 NZ$364
includes taxes & fees
19 Jan - 20 Jan
Peaceful & minutes from the Old Port with private parking

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)
"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 NZ$406
includes taxes & fees
8 Jan - 9 Jan
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Old Orchard Beach
8.0 out of 10, Very good, (24)
"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 NZ$369
includes taxes & fees
8 Jan - 9 Jan
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

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)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is NZ$365
includes taxes & fees
8 Jan - 9 Jan
Charming Studio apartment with WiFi, AC in welcoming Portland

In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt
West Bayside
8.6 out of 10, Excellent, (17)
"Good place to stay in. Safe. However, it would be good to know about the steep and narrow spiral staircase, in case you have lots of heavy luggage."
United States
Omar S.
The price is NZ$156
includes taxes & fees
8 Jan - 9 Jan
In-town no frills 2 bedroom apt

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)
"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 NZ$601
includes taxes & fees
11 Jan - 12 Jan
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

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 favorite 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 depends 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 NZ$233 per night. Entering your travel dates in the search wizard you might find 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?

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 Maine Narrow Gauge Railroad Company and Museum, 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.