Lodging Image

Chebeague Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Chebeague Island vacation rentals

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 AED 441
AED 917 total
includes taxes & fees
28 Jul - 29 Jul
Modern style in historic building in downtown Bath
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, (23 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 AED 419
AED 536 total
includes taxes & fees
9 Jul - 10 Jul
Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Property grounds

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
7.6 out of 10, Good, (14 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is AED 489
AED 613 total
includes taxes & fees
19 Jul - 20 Jul
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
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 AED 463
AED 892 total
includes taxes & fees
11 Jul - 12 Jul
Mid Coast Getaway w/ water views
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 place was lovely, communications with the host were helpful and friendly. Dinner restaurant recommendations were great as well. "
United States
Jane T.
The price is AED 474
AED 597 total
includes taxes & fees
13 Jul - 14 Jul
Large suite/private bath/private entrance on quiet street near Thomas Bay
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
The price is AED 448
AED 1,076 total
includes taxes & fees
16 Jul - 17 Jul
1 Mi to Maine Street! Mcm-style Home in Brunswick
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (59 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AED 771
AED 1,341 total
includes taxes & fees
13 Jul - 14 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 AED 863
AED 1,525 total
includes taxes & fees
12 Jul - 13 Jul
King Size Sun Rise Midcoast Lovely Stay
1 bedroom, WiFi, bed sheets

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.0 out of 10, Very Good, (9 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 AED 347
AED 611 total
includes taxes & fees
9 Jul - 10 Jul
Studio Apartment near downtown Walkable!
Fridge, microwave, oven, stovetop

The Outlet House, Comfortable Cottage

The Outlet House, Comfortable Cottage
Freeport
9.8 out of 10, Exceptional, (58 reviews)
"Awesome place. Thank you for the hospitality!"
United States
Nick F.
The Outlet House, Comfortable Cottage
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 AED 744
AED 1,355 total
includes taxes & fees
21 Jul - 22 Jul
Full sized home
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 AED 735
AED 1,457 total
includes taxes & fees
15 Jul - 16 Jul
Downtown Brunswick New Look Old Charm Next to Bowdoin
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, (43 reviews)
"Beautiful, clean place to stay and dogs welcome "
United States
Anonymous traveler
The price is AED 536
AED 1,348 total
includes taxes & fees
19 Jul - 20 Jul
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Property grounds

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (63 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 1,758 total
includes taxes & fees
2 Aug - 3 Aug
Centerview cottage
Smart TV

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (35 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
The price is AED 845
AED 1,413 total
includes taxes & fees
21 Jul - 22 Jul
Pine Point Beach private, quaint, charming studio.
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 AED 551
AED 1,225 total
includes taxes & fees
28 Jul - 29 Jul
Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
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, (76 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
The price is AED 909
AED 1,475 total
includes taxes & fees
15 Jul - 16 Jul
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Outdoor dining

'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (22 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
The price is AED 1,208
AED 2,366 total
includes taxes & fees
19 Jul - 20 Jul
'Osprey Cottage' South Freeport Home on Casco Bay!
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 AED 1,474
AED 1,606 total
includes taxes & fees
3 Aug - 4 Aug
Fortland Island Campground
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 AED 1,653
AED 2,498 total
includes taxes & fees
23 Jul - 24 Jul
Award Winning Luxury Carriage House a short stroll from town!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chebeague Island Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"We had a great visit and enjoyed the pool. The temperature was refreshing for the adults but chilly for children. The beds were comfortable and clean! The hotel was a walkable distance to shops and restaurants! We would go back again!"
Chelsea 1-night trip
Posted less than an hour ago
Holiday Inn Portland-By the Bay by IHG

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 Wolfe's Neck Farm. 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.