Chebeague Island Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Chebeague Island vacation rentals

Property grounds

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 reviews)
"Clean rooms. Quiet location walkable to much of downtown Bath "
United States
randy k.
The price is ￥29,142
￥35,693 total
includes taxes & fees
May 13 - May 14
Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!
Outdoor dining

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Lovely location "
United States
Michelle S.
The price is ￥44,232
￥86,156 total
includes taxes & fees
May 18 - May 19
Mere Point Sunrise Views at Eastern Shore!
Property grounds

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (59 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 ￥46,221
￥73,949 total
includes taxes & fees
May 12 - May 13
Centerview cottage
Terrace/patio

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 ￥29,613
￥52,772 total
includes taxes & fees
May 12 - May 13
Camp Forever cottage
Fridge, microwave, oven, stovetop

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 ￥66,589
￥100,932 total
includes taxes & fees
May 12 - May 13
Award Winning Luxury Carriage House a short stroll from town!
2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
The price is ￥29,613
￥52,943 total
includes taxes & fees
May 17 - May 18
Large, luxurious geodesic dome - 04
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

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 ￥59,312
￥64,650 total
includes taxes & fees
Jun 7 - Jun 8
Fortland Island Campground
Living area

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
The price is ￥26,079
￥51,928 total
includes taxes & fees
May 12 - May 13
Evalina Hotel
3 bedrooms, WiFi, bed sheets

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is ￥28,790
￥50,606 total
includes taxes & fees
May 13 - May 14
Fantastic Waterfront Views
Smart TV

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (29 reviews)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is ￥25,382
￥47,135 total
includes taxes & fees
May 13 - May 14
Pine Point Beach private, quaint, charming studio.
Beach nearby

Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (64 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is ￥31,305
￥65,034 total
includes taxes & fees
May 13 - May 14
Arlie`s Digs! - One Block To Willard Beach!
Interior

Modern Getaway by the Sea

Modern Getaway by the Sea
Ligonia
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our girls weekend catching up and relaxing in this lovely space, with plenty of room and everything we needed! Host was very responsive. Would definitely stay again!"
United States
Kelley F.
The price is ￥50,921
￥84,894 total
includes taxes & fees
May 12 - May 13
Modern Getaway by the Sea
Exterior detail

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (73 reviews)
"Had a really nice stay. "
United States
John F.
The price is ￥130,436
￥191,703 total
includes taxes & fees
May 12 - May 13
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
TV

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (5 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is ￥19,742
￥37,539 total
includes taxes & fees
May 18 - May 19
Mid Coast Getaway w/ water views
Exterior detail

Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (174 reviews)
"Very cute and comfy. We would definitely stay here again. "
United States
Marie s.
The price is ￥51,234
￥79,413 total
includes taxes & fees
Jun 1 - Jun 2
Glorious getaway on Portland's Eastern Promenade.
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is ￥35,253
￥61,652 total
includes taxes & fees
May 14 - May 15
Full sized home
Interior

Vacation Creation Downtown Brunswick 2King Beds

Vacation Creation Downtown Brunswick 2King Beds
Brunswick
9.6 out of 10, Exceptional, (19 reviews)
"Stayed here while visiting Bowdoin. Great place!"
United States
Deborah B.
The price is ￥24,285
￥61,481 total
includes taxes & fees
May 12 - May 13
Vacation Creation Downtown Brunswick 2King Beds
Outdoor dining

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (41 reviews)
"Great home, great location, very accommodating, clear communication."
United States
Kristi H.
The price is ￥37,157
￥67,826 total
includes taxes & fees
May 12 - May 13
Modern & Sunny House Steps from the Promenade. Private Parking!
Exterior

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, (149 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 ￥14,101
￥18,786 total
includes taxes & fees
May 18 - May 19
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Outdoor dining

The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (95 reviews)
"Cozy and clean great location "
United States
Michele F.
The price is ￥48,571
￥91,710 total
includes taxes & fees
May 12 - May 13
The Globe House on Munjoy Hill - Walk to Breweries
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
"Excelente localido hotel, principais atrações turísticas podem ser alcaoa pé. Quarto ampo, limpo, café da manhã oferecido por um preço justo, funcionários atencidosos e prestativos."
Marcos 3-night trip
Posted 2 hours 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
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Look no further and take a look at our great range of rental properties in Chebeague Island!

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?

Cute House -2 Blocks from Beach: This vacation home rental near Chebeague Island offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

How many vacation rentals are there in Chebeague Island?

Expedia has 3 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 Casco Bay. 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.