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Chebeague Island Vacation Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Chebeague Island vacation rentals

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, (25 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 SAR 428
SAR 549 total
includes taxes & fees
19 Jul - 20 Jul
Captain's Guest Room. Authenticity. Value. Near everything. No fees.
TV, fireplace, books

1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.4 out of 10, Exceptional, (10 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
1 Mi to Maine Street! MCM-Style Home in Brunswick
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 SAR 443
SAR 925 total
includes taxes & fees
22 Jul - 23 Jul
Modern style in historic building in downtown Bath
House (2 Bedrooms) | 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
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, (154 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 SAR 460
SAR 584 total
includes taxes & fees
29 Jul - 30 Jul
Large suite/private bath/private entrance on quiet street near Thomas Bay
TV

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 SAR 690
SAR 1,145 total
includes taxes & fees
3 Aug - 4 Aug
Mid Coast Getaway w/ water views
Property grounds

Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 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 SAR 913
SAR 1,478 total
includes taxes & fees
26 Jul - 27 Jul
Modern cabin w/ full bath & kitchenette - 03
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 SAR 776
SAR 845 total
includes taxes & fees
19 Jul - 20 Jul
Fortland Island Campground
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 SAR 620
SAR 1,232 total
includes taxes & fees
20 Jul - 21 Jul
King Size Sun Rise Midcoast Lovely Stay
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (29 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 SAR 916
SAR 1,437 total
includes taxes & fees
26 Jul - 27 Jul
Sunny Spot with Private Parking.
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, (45 reviews)
"Beautiful, clean place to stay and dogs welcome "
United States
Anonymous traveler
The price is SAR 548
SAR 1,358 total
includes taxes & fees
19 Jul - 20 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 SAR 545
SAR 1,236 total
includes taxes & fees
2 Aug - 3 Aug
Downtown Brunswick New Look Old Charm Next to Bowdoin
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (54 reviews)
"Wonderful stay!"
United States
Erika T.
The price is SAR 760
SAR 1,394 total
includes taxes & fees
21 Jul - 22 Jul
Full sized home
Beach nearby, sun loungers, beach towels

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Grand Beach
9.8 out of 10, Exceptional, (47 reviews)
"Stay was good. It was clean well decorated and equipped with everything you need"
United States
Tom K.
The price is SAR 563
SAR 1,257 total
includes taxes & fees
28 Jul - 29 Jul
Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Property grounds

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (64 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 SAR 1,108
SAR 1,793 total
includes taxes & fees
19 Jul - 20 Jul
Centerview cottage
Coffee/tea maker, fridge, microwave, oven

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 SAR 995
SAR 1,928 total
includes taxes & fees
20 Jul - 21 Jul
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
1 bedroom, WiFi, bed sheets

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very Good, (10 reviews)
"Check in process was smooth and description of area was accurate though cleanliness of unit left a lot to be desired. There was a lot of hair all over the apartment floor and bedding when we arrived with old stains in bedding. Booked 2 nights and ended up getting a hotel for the 2nd day."
United States
Raul
The price is SAR 434
SAR 712 total
includes taxes & fees
11 Aug - 12 Aug
Studio Apartment near downtown Walkable!
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, (11 reviews)
"The house matches exactly what was described online. It's clean and cozy in a quite neighborhood. I'd rate it a five star and highly recommend!"
United States
Shisheng
The price is SAR 1,690
SAR 2,554 total
includes taxes & fees
24 Jul - 25 Jul
Award Winning Luxury Carriage House a short stroll from town!
Property grounds

Modern dome w/ full bath + spa access - 04

Modern dome w/ full bath + spa access - 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 SAR 1,443
SAR 2,188 total
includes taxes & fees
23 Jul - 24 Jul
Modern dome w/ full bath + spa access - 04
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

Grand Beach Inn

Grand Beach Inn

8/10 Good
"Rooms were updated, modern, and very clean. Beds were very comfortable. Sound insulation was lacking, though, so it was tough to sleep since we were next to a hallway door that made noise every time the wind blew. Parking was very limited, so try to bring only one car, or make arrangements for a second car off-site (they can accommodate 2 cars if they are not full, but on a busy weekend, they understandably only have room for one car per room). Pool was small but clean and well-maintained. Staff was very helpful and kind. On-site bistro had good food and drinks; one night, our service was very fast, and the next it was slow, but with live music and such nice servers, it didn't bother us much. Fabulous location, right across a public entry to the quiet parts of OOB and with a trolley stop right out front that brings you to the pier. Pier is walkable, about 1-1.5 miles, but it's nice being far enough way that you can escape the hustle and bustle if you want. Would definitely stay here again."
Maura 2-night trip
Posted 1 hour ago
Grand Beach Inn

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?

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

How many vacation rentals are there in Chebeague Island?

Expedia has 4 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.