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Chebeague Island Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Chebeague Island holiday rentals

Exterior

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, (153 reviews)
The price is HK$933
HK$1,188 total
includes taxes & fees
2 Jul - 3 Jul
Large suite/private bath/private entrance on quiet street near Thomas Bay
Outdoor dining

Captain's Guest Room. Authenticity. Value. Near everything. No fees.

Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Bath
8.2 out of 10, Very good, (22 reviews)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
The price is HK$894
HK$1,145 total
includes taxes & fees
29 Jun - 30 Jun
Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Interior

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
1 Mi to Maine Street! Mcm-style Home in Brunswick
TV

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.4 out of 10, Exceptional, (6 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is HK$1,235
HK$2,190 total
includes taxes & fees
30 Jun - 1 Jul
Mid Coast Getaway w/ water views
Interior

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (10 reviews)
"Clean comfortable and right downtown"
United States
stephen e.
The price is HK$925
HK$1,923 total
includes taxes & fees
29 Jun - 30 Jun
Modern style in historic building in downtown Bath
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 HK$1,646
HK$2,871 total
includes taxes & fees
16 Jul - 17 Jul
Camp Forever cottage
Dining

King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
10.0 out of 10, Exceptional, (15 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 HK$1,842
HK$3,256 total
includes taxes & fees
1 Jul - 2 Jul
King Size Sun Rise Midcoast Lovely Stay
Smart TV

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (33 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
The price is HK$1,129
HK$2,188 total
includes taxes & fees
28 Jun - 29 Jun
Pine Point Beach private, quaint, charming studio.
2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is HK$3,571
HK$5,260 total
includes taxes & fees
11 Jul - 12 Jul
Large, luxurious geodesic dome - 04
Property grounds

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"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 HK$2,244
HK$3,488 total
includes taxes & fees
5 Jul - 6 Jul
Modern, Luxurious Cabin in the Woods - 03
Beach nearby, sun-loungers, beach towels

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Pine Point
9.6 out of 10, Exceptional, (42 reviews)
"Beautiful, clean place to stay and dogs welcome "
United States
Anonymous traveller
The price is HK$1,143
HK$2,887 total
includes taxes & fees
1 Jul - 2 Jul
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Interior

Downtown Brunswick New Look Old Charm Next to Bowdoin

Downtown Brunswick New Look Old Charm Next to Bowdoin
Brunswick
9.8 out of 10, Exceptional, (21 reviews)
"We really enjoyed our visit with family and friends and the location was perfect for what we needed. "
United States
Eliza
The price is HK$1,294
HK$2,769 total
includes taxes & fees
30 Jun - 1 Jul
Downtown Brunswick New Look Old Charm Next to Bowdoin
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (53 reviews)
"Wonderful stay!"
United States
Erika T.
The price is HK$1,588
HK$2,911 total
includes taxes & fees
1 Jul - 2 Jul
Full sized home
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (27 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 HK$2,015
HK$3,111 total
includes taxes & fees
8 Jul - 9 Jul
Sunny Spot with Private Parking.
Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Apartment was very cute, clean, and just what I was looking for. Jennifer was very accommodating and understanding "
United States
Jolee S.
The price is HK$1,513
HK$2,589 total
includes taxes & fees
29 Jun - 30 Jun
Peaceful & minutes from the Old Port with private parking
Property grounds

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (62 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 HK$2,313
HK$3,744 total
includes taxes & fees
28 Jun - 29 Jun
Centerview cottage
Egyptian cotton sheets, premium bedding, down duvets, 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 HK$3,227
HK$3,517 total
includes taxes & fees
27 Jul - 28 Jul
Fortland Island Campground
Interior

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, (74 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
The price is HK$1,517
HK$2,628 total
includes taxes & fees
1 Jul - 2 Jul
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Interior

East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (38 reviews)
"Clean, great location, excellent communication with host, perfectly furnished for our group"
United States
Elizabeth P.
The price is HK$2,602
HK$4,079 total
includes taxes & fees
14 Jul - 15 Jul
East end. Walk to food, beer and downtown fun.
Fridge, microwave, oven, stovetop

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.6 out of 10, Exceptional, (33 reviews)
"Wonderful location. It’s right next to Bowdoin. There is a great coffee shop a block away and a grocery store within easy walking distance. The place was spotless. "
United States
Mike S.
The price is HK$1,921
HK$3,838 total
includes taxes & fees
30 Jun - 1 Jul
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

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

10/10 Excellent
"Breakfast was excellent and overall stay pleasant. It’s a drive to Old Port."
Yoginand 2-night trip
Posted 8 hours ago
Embassy Suites by Hilton Portland Maine

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 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?

Cozy & Quiet Home in Portland Maine. One Bedroom, Private Bathroom “No Kitchen”: This holiday home rental outside of Chebeague Island is located on the beach, and offers a fireplace, air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and an electric kettle.

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 Wolfe's Neck Farm. 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.