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Chebeague Island Vacation Rentals

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chebeague Island vacation rentals

Terrace/patio

1. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (63 reviews)
"Wonderful stay!"
United States
Erika T.
The price is AED 744
AED 1,363 total
includes taxes & fees
22 Sep - 23 Sep
Full sized home
Property grounds

2. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (12 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 AED 749
AED 1,715 total
includes taxes & fees
16 Sep - 17 Sep
Orchid Harbor, Bailey Island 3BR
House (2 Bedrooms) | Interior

3. 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 AED 375
AED 996 total
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Maine Street! Mcm-style Home in Brunswick
TV

4. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is AED 579
AED 1,042 total
includes taxes & fees
1 Sep - 2 Sep
Mid Coast Getaway w/ water views
Terrace/patio

5. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (65 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AED 771
AED 1,345 total
includes taxes & fees
25 Aug - 26 Aug
Camp Forever cottage
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

6. 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 AED 972
AED 1,660 total
includes taxes & fees
25 Aug - 26 Aug
Fortland Island Campground
Exterior

7. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (164 reviews)
"Susan and Jeff were amazing hosts! There were so kind, thoughtful and welcoming. The suite was extremely spacious, well decorated and very comfortable. We were very close to the Air Show which was the reason for our trip. They gave us great instructions for a short cut to the airfield and amazing dinner recommendations. We could not have chosen a better place to stay. We highly recommend this place!"
United States
Asha
The price is AED 474
AED 597 total
includes taxes & fees
3 Sep - 4 Sep
Large suite/private bath/private entrance on quiet street near Thomas Bay
TV

8. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.6 out of 10, Excellent, (9 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is AED 386
AED 466 total
includes taxes & fees
25 Aug - 26 Aug
Private Entrance Residential Portland
Interior

9. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (11 reviews)
"Great location! We spent very little time in the room, but it was a great place to come back and crash! "
United States
Kristina M.
The price is AED 371
AED 829 total
includes taxes & fees
22 Sep - 23 Sep
Modern style in historic building in downtown Bath
Outdoor dining

10. Captain's Guest Room. Authenticity. Great Value. Large yard. Walk to everything.

Captain's Guest Room. Authenticity. Great Value. Large yard. Walk to everything.
Bath
8.4 out of 10, Very Good, (27 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is AED 419
AED 657 total
includes taxes & fees
30 Aug - 31 Aug
Captain's Guest Room. Authenticity. Great Value. Large yard. Walk to everything.
Property grounds

11. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (8 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 AED 1,002
AED 1,584 total
includes taxes & fees
26 Aug - 27 Aug
Modern cabin w/ full bath & kitchenette - 03
Dining

12. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (18 reviews)
"Great location surroundings a little unkept but tis the spring cleanup season. Excellent accommodation and located near town shopping but quiet neighborhood"
United States
Douglas H.
The price is AED 533
AED 1,039 total
includes taxes & fees
7 Sep - 8 Sep
King Size Sun Rise Midcoast Lovely Stay
1 bedroom, WiFi, bed sheets

13. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very Good, (15 reviews)
"I will admit the location and surrounding areas are a bit sketchy, but, once inside, we felt super secure. There are multiple doors and gates with locks to ensure safety. Place was clean and had everything we needed for a quick stay."
United States
Krysta
The price is AED 405
AED 681 total
includes taxes & fees
1 Sep - 2 Sep
Studio Apartment near downtown Walkable!
Interior

14. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Excellent in every way."
United States
Robert B.
The price is AED 638
AED 1,336 total
includes taxes & fees
16 Sep - 17 Sep
Willard Beach–Apartment Near Portland & Parks
Interior

15. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (31 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 AED 724
AED 1,201 total
includes taxes & fees
22 Sep - 23 Sep
Sunny Spot with Private Parking.
Exterior detail

16. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (143 reviews)
"Owner was so accommodating!"
United States
Kiernan
Adorable Portland getaway on the Eastern Promenade
Property grounds

17. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (39 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is AED 513
AED 1,736 total
includes taxes & fees
31 Aug - 1 Sep
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Property grounds

18. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (68 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 AED 1,084
AED 1,762 total
includes taxes & fees
29 Aug - 30 Aug
Centerview cottage
Smart TV, fireplace, foosball, books

19. Cozy and charming coastal retreat

Cozy and charming coastal retreat
West Point
9.8 out of 10, Exceptional, (33 reviews)
"My family and I had an amazing time at the schoolhouse. It is much bigger than the pictures show! Great beds, the couches will force you to nap, and we had so much fun exploring the area. They had everything you need for fun at the beach, and lots of options for kids to keep busy. Highly recommend!"
United Kingdom
Byrony S.
Cozy and charming coastal retreat
Dining

20. Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (83 reviews)
"It was nice if you like being right in town. There is no view and it's a bit noisy."
United States
Nancy S.
The price is AED 617
AED 1,884 total
includes taxes & fees
25 Aug - 26 Aug
Elegant condo - walk to Portland's best restaurants & Old Port
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

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Location of the hotel is one block from the Old Port with numerous stores and restaurants. Hotel has its own parking garage with unlimited access. Parking fee for hotel guests is $45 per day."
john 3-night trip
Posted 9 hours ago
Portland Harbor Hotel

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?

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This vacation home rental near Chebeague Island is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Chebeague Island?

Expedia has 5 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 Winslow Memorial Park. Wolfe's Neck Woods State Park and Bailey Island Bridge 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.