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Holiday Rentals in Chebeague Island

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Our top choices for Chebeague Island holiday rentals

1. Great suburban location close to town!

Great suburban location close to town!
Deering Center
9.6 out of 10, Exceptional, (4 reviews)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
The price is €95
includes taxes & fees
1 Nov - 2 Nov
Great suburban location close to town!

2. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is €393
includes taxes & fees
16 Nov - 17 Nov
Orchid Harbor, Bailey Island 3BR

3. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (11 reviews)
"Location and parking were perfect for our first visit to Portland"
United States
Linda
Willard Beach–Apartment Near Portland & Parks

4. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.0 out of 10, Very good, (17 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
Portland 1-bedroom with enclosed porch & parking

5. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (24 reviews)
"Location was convenient to everything and building was super secure."
United States
Rose
The price is €121
includes taxes & fees
19 Nov - 20 Nov
Studio Apartment near downtown Walkable!

6. Cabin w/ bath + kitchenette | Hot tub add-on - 03

Cabin w/ bath + kitchenette | Hot tub add-on - 03
Freeport
9.8 out of 10, Exceptional, (10 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
The price is €328
includes taxes & fees
29 Oct - 30 Oct
Cabin w/ bath + kitchenette | Hot tub add-on - 03

7. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is €347
includes taxes & fees
17 Nov - 18 Nov
Mere Point Sunrise Views at Eastern Shore!

8. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (34 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is €138
includes taxes & fees
1 Nov - 2 Nov
Beautiful 1st Floor Apartment & Amazing Shower

9. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (80 reviews)
"Wonderful stay!"
United States
Erika T.
The price is €332
includes taxes & fees
2 Nov - 3 Nov
Full sized home

10. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (29 reviews)
"Lovely apartment, in a pristine location. Very spacious and comfortable all around. Highly recommended this place for your next stay in Portland, Maine!"
United States
Gintare V.
Bright & Spacious Apartment with Amazing Shower

11. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (157 reviews)
"Owner was so accommodating!"
United States
Kiernan
Adorable Portland getaway on the Eastern Promenade

12. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
The price is €211
includes taxes & fees
3 Nov - 4 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

13. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (63 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is €326
includes taxes & fees
22 Nov - 23 Nov
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

14. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (127 reviews)
"Really nice room and location"
United States
Victoria
The price is €255
includes taxes & fees
18 Nov - 19 Nov
The Weldon Hotel

15. Casco Bay Oceanfront Retreat by Everrow

Casco Bay Oceanfront Retreat by Everrow
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"What can I say about my stay; peaceful, beautiful views, and relaxing! Home was clean with modern finishes but super comfortable for my four guests. The downstairs area is very private from the main floor. The yard was a great space where we had our outdoor fire looking up at the stars at night. The deck was perfect for our family lunch and dinners. We took chairs down to the beach area to sit closer to the water which was perfect. It's super close to town, Wolfe's Neck and other amenities....
United States
Lisa E.
The price is €809
includes taxes & fees
4 Nov - 5 Nov
Casco Bay Oceanfront Retreat by Everrow

16. Modern dome w/ full bath | Hot tub add-on - 04

Modern dome w/ full bath | Hot tub add-on - 04
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is €307
includes taxes & fees
29 Oct - 30 Oct
Modern dome w/ full bath | Hot tub add-on - 04

17. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
Sunny Spot with Private Parking.

18. Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.4 out of 10, Exceptional, (95 reviews)
"Excellent property in Portland. Clean with amenities needed for any stay. Easy access to downtown. Hosts communicate exceptionally well and property is everything it promotes!"
United States
Adam Y.
The price is €323
includes taxes & fees
1 Nov - 2 Nov
Walk to Old Port ♦ West End Condo ♦ Parking

19. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is €177
includes taxes & fees
29 Oct - 30 Oct
Mid Coast Getaway w/ water views

20. The Bow Street Abode / Charming 2 BR Retreat

The Bow Street Abode / Charming 2 BR Retreat
Freeport
10.0 out of 10, Exceptional, (28 reviews)
"Great location and super clean apartment!"
United States
Jo B.
The price is €393
includes taxes & fees
2 Nov - 3 Nov
The Bow Street Abode / Charming 2 BR Retreat
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, apart-hotels, 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 €119 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?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This holiday home rental outside of Chebeague Island is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Chebeague Island?

Expedia has 4 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 Little John Island Preserve. 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.