Chebeague Island Vacation Rentals

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Check prices for these dates

Tonight
Nov 10 - Nov 11
Tomorrow
Nov 11 - Nov 12
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Chebeague Island

Property grounds
Captain's Guest Room w/private bath. Walk to everything.

Captain's Guest Room w/private bath. Walk to everything.

Bath
8.2 out of 10, Very Good, (21)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
United States
Benjamin E.
The price is ￥8,745
￥24,583 total
includes taxes & fees
Nov 11 - Nov 12
Captain's Guest Room w/private bath. Walk to everything.
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, (143)
"Gorgeous, comfortable and incredibly welcoming and nice hosts. Great location for visiting with old friends and visiting the beautiful coastline and towns."
United States
Elizabeth R.
The price is ￥13,808
￥18,395 total
includes taxes & fees
Nov 11 - Nov 12
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Dining
Escape to Positive Outlook

Escape to Positive Outlook

West Point
10.0 out of 10, Exceptional, (2)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is ￥16,109
￥32,912 total
includes taxes & fees
Dec 4 - Dec 5
Escape to Positive Outlook
Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library
The Weldon Hotel

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (86)
"Absolutely beautiful place to stay. "
United States
James
The price is ￥28,306
￥42,361 total
includes taxes & fees
Dec 7 - Dec 8
The Weldon Hotel
Smart TV
Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower

Parkside
9.0 out of 10, Wonderful, (25)
"My brother in law and I stayed here while my husband was hospitalized at the Maine Med and it was a lovely property. Everything was clean and organized, check in was easy and the hosts were responsive and kind. I would stay here again!"
United States
Lillian L.
The price is ￥8,269
￥21,555 total
includes taxes & fees
Nov 11 - Nov 12
Beautiful 1st Floor Apartment & Amazing Shower
Interior
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Old Orchard Beach
10.0 out of 10, Exceptional, (32)
"Great location and great host. "
United States
Dwight P.
The price is ￥30,531
￥68,229 total
includes taxes & fees
Nov 18 - Nov 19
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Interior
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 ￥14,575
￥40,636 total
includes taxes & fees
Nov 11 - Nov 12
Brunswick Downtown Sugar Cube next to Bowdoin
Exterior detail
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)
"Cozy little cotrage"
United States
craig H.
The price is ￥12,274
￥29,432 total
includes taxes & fees
Nov 11 - Nov 12
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Dining
Sunny Spot with Private Parking.

Sunny Spot with Private Parking.

2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"Had a great stay here! The place was very clean and well-equipped. Convenient parking and a short drive to Portland center. Would stay here again!"
United States
Emre G.
The price is ￥12,128
￥27,433 total
includes taxes & fees
Nov 12 - Nov 13
Sunny Spot with Private Parking.
1 bedroom, desk, free WiFi, bed sheets
Spacious Studio Near Sebago Lake

Spacious Studio Near Sebago Lake

2.0 star property
Windham
10.0 out of 10, Exceptional, (1)
"Host was very welcoming and check in was simple "
United States
Michael C.
The price is ￥14,115
￥18,730 total
includes taxes & fees
Nov 11 - Nov 12
Spacious Studio Near Sebago Lake
Interior
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

Munjoy Hill
9.6 out of 10, Exceptional, (125)
"Welcoming small apartment in a beautiful Portland neighborhood. Clean and stocked with everything we needed. Very helpful hosts. "
United States
Annalise M.
The price is ￥14,882
￥28,763 total
includes taxes & fees
Nov 16 - Nov 17
Adorable Portland getaway on the Eastern Promenade
Fridge, microwave, stovetop, coffee/tea maker
The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace

Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable and homey Great location to the outlets. "
United States
Patricia C.
The price is ￥13,117
￥25,168 total
includes taxes & fees
Nov 11 - Nov 12
The Outlet Studio, Rustic Comfort w Fireplace
3 bedrooms, WiFi
Fantastic Waterfront Views

Fantastic Waterfront Views

West Point
9.6 out of 10, Exceptional, (13)
"The place is amazing with lots of room for a family, and great views of the water from almost everywhere. The neighborhood is quiet and the people were very friendly. "
United States
Joseph V.
The price is ￥19,331
￥41,262 total
includes taxes & fees
Nov 30 - Dec 1
Fantastic Waterfront Views
Property grounds
Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03

Freeport
10.0 out of 10, Exceptional, (6)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is ￥17,797
￥35,620 total
includes taxes & fees
Dec 10 - Dec 11
Modern, Luxurious Cabin in the Woods - 03
Smart TV, books
Little Lincoln beautiful home

Little Lincoln beautiful home

Brunswick
9.0 out of 10, Wonderful, (13)
"Nice little cottage, lots of sun, great layout, full kitchen which is so important to me, and less than a block to the commercial center! Plenty of parking, easy to unload and load my car, only a step up or two into the property which was perfect for my very small dog. "
United States
Linda B.
The price is ￥11,046
￥36,288 total
includes taxes & fees
Nov 18 - Nov 19
Little Lincoln beautiful home
Fridge, microwave, oven, stovetop
King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay

Topsham
10.0 out of 10, Exceptional, (14)
"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 ￥13,654
￥35,619 total
includes taxes & fees
Nov 11 - Nov 12
King Size Sun Rise Midcoast Lovely Stay
Interior
Serenity between the lakes and seashore

Serenity between the lakes and seashore

Westbrook
9.8 out of 10, Exceptional, (23)
"Good location near lots of hiking and not far from Portland "
United States
Laura P.
The price is ￥15,035
￥48,161 total
includes taxes & fees
Nov 29 - Nov 30
Serenity between the lakes and seashore
Smart TV, books
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, (27)
" Very spacious, clean and beautiful."
United States
robert p.
The price is ￥18,257
￥50,837 total
includes taxes & fees
Nov 11 - Nov 12
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Outdoor dining
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)
"My husband and I had a wonderful weekend in South Portland and enjoyed the central location and charming touches of Jennifer’s apartment. The space is lovely, exactly as described in the listing. The communication was clear and detailed. We will definitely return!"
United States
Caitlin C.
The price is ￥12,780
￥30,319 total
includes taxes & fees
Nov 11 - Nov 12
Peaceful & minutes from the Old Port with private parking
Outdoor dining
Vacation Creation Downtown Brunswick 2King Beds

Vacation Creation Downtown Brunswick 2King Beds

Brunswick
9.6 out of 10, Exceptional, (18)
"Overall, this apartment is a good place to stay in Brunswick. It was the right size for 2 adults. It was cozy even in the dead of winter. It was clean, tidy, and had a fresh appearance. The beds were comfortable and the bathroom well-maintained and neat, with very good water pressure. It is a short 2-block walk to Maine Street shops or grocery store, and a 10 minute walk to campus.There are only 4 detractions we had, all MINOR, but which grew mildly irksome after two weeks - if you are only...
United States
Eric B.
The price is ￥19,945
￥48,162 total
includes taxes & fees
Nov 16 - Nov 17
Vacation Creation Downtown Brunswick 2King Beds
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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent
"Very clean hotel"
Marijana 2-night trip
Posted 1 day ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

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 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?

New 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 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.