Chebeague Island Vacation Rentals

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Vacation Rentals in Chebeague Island

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
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.
$110 nightly
The price is $120
Nov 4 - Nov 5
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Property grounds
Captain's Guest Room w/private bath. Walk to everything.
Captain's Guest Room w/private bath. Walk to everything.
8.2 out of 10, Very Good, (20)
"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.
$135 nightly
The price is $147
Nov 4 - Nov 5
Total with taxes and fees
Captain's Guest Room w/private bath. Walk to everything.
Interior
Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick Downtown Sugar Cube next to Bowdoin
8.4 out of 10, Very Good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
$230 nightly
The price is $251
Nov 5 - Nov 6
Total with taxes and fees
Brunswick Downtown Sugar Cube next to Bowdoin
Interior
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
10.0 out of 10, Exceptional, (4)
"Beautiful location!! Very comfortable and clean home "
United States
Beth L.
$519 nightly
The price is $566
Nov 4 - Nov 5
Total with taxes and fees
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
Dining
Sunny Spot with Private Parking.
Sunny Spot with Private Parking.
2.0 star property
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.
$165 nightly
The price is $180
Nov 4 - Nov 5
Total with taxes and fees
Sunny Spot with Private Parking.
Interior
Beach Plum Cottage - on Popham Beach!
Beach Plum Cottage - on Popham Beach!
8.0 out of 10, Very Good, (1)
"Our stay was overwhelmingly good. There is no ac but it was manageable with open windows (first week in August). You can walk to a section of beach easily (along the river just before it meets the ocean). The restaurant next door was yummy but the service was slow only because they were really busy and maybe not enough staff? But food was great. My only two issues were that we were awakened at 6am with beeping from the delivery trucks directly outside our window and that the “common areas”...
United States
Joanna K.
Beach Plum Cottage - on Popham Beach!
Fridge, microwave, oven, stovetop
King Size Sun Rise Midcoast Lovely Stay
King Size Sun Rise Midcoast Lovely Stay
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.
$213 nightly
The price is $232
Nov 4 - Nov 5
Total with taxes and fees
King Size Sun Rise Midcoast Lovely Stay
Terrace/patio
Modern, Luxurious, Cabin in the Woods - 17 (ADA)
Modern, Luxurious, Cabin in the Woods - 17 (ADA)
10.0 out of 10, Exceptional, (3)
"Please listen closely!! If you pass this place up, I truly feel sorry for you. I am on a first time adventure to Maine from Indiana and this is my FAVORITE place stay of ALL TIME. I wish I had done my homework and planned more time at Desert of Maine. Our cabin was cozy after a nice evening by the fire. Loved the shower!! I will definitely return for a girl's trip with my sisters!! (Cabin 17)"
United States
Amanda V.
$223 nightly
The price is $243
Nov 24 - Nov 25
Total with taxes and fees
Modern, Luxurious, Cabin in the Woods - 17 (ADA)
Interior
Adorable Portland getaway on the Eastern Promenade
Adorable Portland getaway on the Eastern Promenade
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.
$157 nightly
The price is $171
Nov 4 - Nov 5
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
Private kitchen
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok
7.2 out of 10, Good, (12)
"The property is charmless. Not clean. Linens and towels are disgusting. Very disappointed. Especially for the price I paid."
United States
Darla J.
$228 nightly
The price is $249
Nov 4 - Nov 5
Total with taxes and fees
Renovated 2Bd Cottage 10min walk to Beach. Pets Ok
Outdoor dining
Vacation Creation Downtown Brunswick 2King Beds
Vacation Creation Downtown Brunswick 2King Beds
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.
$288 nightly
The price is $314
Nov 16 - Nov 17
Total with taxes and fees
Vacation Creation Downtown Brunswick 2King Beds
Beach nearby, sun loungers, beach towels
Beach House ∆ Prime Location ∆ Steps to the Ocean
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (55)
"We had a wonderful stay the weekend after Christmas. The home had absolutely everything we needed and was both comfortable and beautiful! Everything was clearly labeled and so easy settle in. Very close to the beach which was awesome to visit even in the winter!"
United States
Elizabeth M.
$444 nightly
The price is $484
Nov 4 - Nov 5
Total with taxes and fees
Beach House ∆ Prime Location ∆ Steps to the Ocean
Fridge, microwave, oven, stovetop
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
8.8 out of 10, Excellent, (21)
"Great location for baileys island and popham"
United States
Anonymous traveler
$351 nightly
The price is $383
Nov 17 - Nov 18
Total with taxes and fees
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
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)
9.8 out of 10, Exceptional, (27)
" Very spacious, clean and beautiful."
United States
robert p.
$304 nightly
The price is $331
Nov 10 - Nov 11
Total with taxes and fees
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Outdoor dining
Camp Forever cottage
Camp Forever cottage
9.6 out of 10, Exceptional, (56)
"Nice, quiet location. Bed is super comfortable, and everything is neat and clean inside. We were a little confused which kayaks we could use and how to get them down to the water, and we were encouraged to use life vests, but there were none available (and we did not bring any with us). Otherwise, hosts were very responsive and we had a nice time."
United States
Lisa K.
$355 nightly
The price is $387
Nov 30 - Dec 1
Total with taxes and fees
Camp Forever cottage
Outdoor dining
Waterfront Access with Kayaks, Private Deck and a Firepit
Waterfront Access with Kayaks, Private Deck and a Firepit
2.0 star property
10.0 out of 10, Exceptional, (3)
"Comfortably fit the eight of us who stayed for a family wedding."
United States
Jason G.
$563 nightly
The price is $620
Nov 4 - Nov 5
Total with taxes and fees
Waterfront Access with Kayaks, Private Deck and a Firepit
Smart TV
Beautiful 1st Floor Apartment & Amazing Shower
Beautiful 1st Floor Apartment & Amazing Shower
9.0 out of 10, Wonderful, (24)
"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.
$145 nightly
The price is $158
Nov 5 - Nov 6
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
Interior
Serenity between the lakes and seashore
Serenity between the lakes and seashore
9.8 out of 10, Exceptional, (23)
"Good location near lots of hiking and not far from Portland "
United States
Laura P.
$312 nightly
The price is $340
Nov 29 - Nov 30
Total with taxes and fees
Serenity between the lakes and seashore
Interior
Charming Studio apartment with WiFi, AC in welcoming Portland
Charming Studio apartment with WiFi, AC in welcoming Portland
9.6 out of 10, Exceptional, (11)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
United States
Kirsten
$211 nightly
The price is $230
Nov 4 - Nov 5
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
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
"Great stay "
Hillary 1-night trip
Posted 2 days ago
Embassy Suites by Hilton Portland Maine

Find out more about Chebeague Island

Everything you need to know about Chebeague Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chebeague Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chebeague Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chebeague Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chebeague Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chebeague Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $145 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chebeague Island rentals

At Expedia, we put the best Chebeague Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chebeague Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chebeague Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chebeague Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.