
Chebeague Island island rentals
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Top-rated island rentals in Chebeague Island
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Chebeague Island vacation rentals
Chebeague Island vacation rentals

Tranquil waterfront cottage
This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

Opening May 16th
Accomodations exactly as shown in pictures. Kitchen is definitely well equipped with all of the essentials and more. Ice cream shop right next door is great and The Lobster Pound on the other side is excellent. You can walk to shops and restaurants downtown but we had no problem finding parking in the evening so we could enjoy the awesome restaurants.

Luxury Beach Front Condo! Prime Location!
Excellent place, sunset and sunrise is just beautiful right from your private balcony, plenty of things to do even on rainy days, huge selection of places to eat, great bands play right on the premises, great people and atmosphere. The condo was very clean and has everything you need. I would love to stay again!

Faith Lane with community pool
Beautiful house! Lots of space and had everything you need for your visit. The community pool was great too. Very close to Portland and easy to get to other areas of Maine from the location. Jason was a great host and very responsive and helpful! Only minor complaint was mattresses upstairs were a little on the firm side but other than that the house was great!

Summer Vacation Rental with 3 beds/2 bath
This place is within walking distance to the beach, miniature golf, restaurants, an amusement park and a place that will steam lobsters for you. We went to the lobster place twice to bring these large beauties home. 1 bathroom was upstair with the bedrooms, and 1 downstairs. There is a picnic table for outdoor dining. Our family of 4 adults and 2 children had a great vacation with weather in the 70s and being from Texas where the temperature was 100+, it was heaven.

Over 1000 Five Star Reviews! Walk to Dock Square !
I had a wonderful stay at this cozy Airbnb. The location was perfect, right in the heart of downtown, so it was super convenient to walk to shops, restaurants, and everything else we wanted to see. We also loved that it was dog friendly, which made our trip even better. The place was clean, comfortable, and exactly as described. The host was friendly and responsive, making check-in a breeze. Highly recommend!

15A -5 Min Walk to Beach&Pier. Quaint Cottage
This was the perfect place for our beach vacation. VERY quick walk to the beach and town and the perfect amount of space for our family. The place was clean and Jeanette always responded quickly if there was an issue. We had a great stay and would definitely stay again in the future!!

Unit 3 Getaway - Perfect for Families!
Perfect size for our family of 4. Location to the beach was a short walk across the street. Kitchen was modern and clean. The beds were comfortable. Pillows were available to use but we brought ours from home. Two bathrooms are always a plus with two teenage girls, only request from them was a full length mirror in the 2nd bedroom to check out their outfits. Owner reached out during our stay to check in and see if everything was going well. Very thoughtful. Would highly recommend a stay here.
Other great vacation rentals in Chebeague Island

Gorgeous 4 BR home with HOT TUB
The home was beautiful and matched the photos online. Clean and inviting! Gregory was responsive while booking and during our stay. Very kind and would stay here again for another girls weekend get away!

Lakefront Getaway
We LOVED our weekend on Arrowhead Lake! Great house for families. We have three teenagers and loved having separate spaces for everyone, as well as places we could all gather together, inside or out! There was something for everyone! Perfectly set up for those who love to cook, fish, kayak, walk or just read a book outside! Nearby we enjoyed the farm stands, our first attempt at disc golf, my son's first catch of a small mouth bass and shopping at the Limerick Grocery Store (very well stocked!). We hope to return again soon!! Elizabeth was a wonderful and attentive host!

All seasons Lake House next to ski areas
Had a great stay at the cabin. The lake and surrounding mountains are beautiful. Lake was fun to fish off dock and using canoe. Nearby town Bethel has a few nice restaurants and there are a number of easily accessible day hiking spots nearby. The beds are super comfortable as well. Overall a great stay!

Spring into the season eating lobsters w/friends
Very nice place to stay big nice and clean recommended this place to everyone looking for a good place big and clean this the right place

cozy 3 bedroom ranch with deck and screen porch
The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.

Quiet cozy cottage close to restaurants, beach
Lori’s place was very cozy and a great screened in back porch. Perfect for morning coffee while taking in the scenery. Easily walkable to downtown and restaurants and right down the street from the beach. Nicely located for all things. We rented a car on our stay and travelled to Portland, Portsmouth NH and then close by towns to Kennebunk. All under an hours drive. We enjoyed our stay at Lori’s place.

Waterfront Farmhouse with Modern Flair!
The home was very welcoming and accommodating for our family of 5. The views were spectacular at sunrise, sunset and during the snowstorm. Bald Eagles and hawks would land in the trees right in front of the house. Also, there was a skating pond down the street my family love to visit almost each evening. There was an alarm going off as soon as we arrived, Debbi was incredibly fast responding and sending someone to check it out clear it up. On the plus someone came and plowed the driveway after the snowstorm it was great. She left a basket of local food and my family ate it up. We are so thankful for our relaxing week and would love to return.

Cabin on the hill!
Eric was a great host. He was very responsive and friendly in all communications. The home was perfect for our family of 5 and three dogs. After long days of hiking we really enjoyed the hot tub! We had a great time.
Quick stats about vacation rentals in Chebeague Island
Total rentals
180 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
4.2K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Frequently Asked Questions
Do cottage rentals in Chebeague Island have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Chebeague Island. Enjoy a tailored experience with all the comforts you desire.
Are there house rentals with a dedicated workspace in Chebeague Island?
Yes! Work meets play with ease at over 40 house rentals in Chebeague Island featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Chebeague Island?
Experience the best of Chebeague Island with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Chebeague Island have a bbq area?
Absolutely! We offer over 30 cottage rentals with a bbq area in Chebeague Island. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cottage rentals in Chebeague Island?
Chebeague Island has more than 50 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there pet-friendly house rentals in Chebeague Island?
Four-legged friends are welcome in Chebeague Island. Choose from more than 40 house rentals for guests traveling with pets.
Do cottage rentals in Chebeague Island have wifi?
Absolutely! We offer over 50 cottage rentals with wifi in Chebeague Island. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cottage Rentals in Chebeague Island?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 30 homes with a bbq area, over 50 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Cottage rentals Chebeague Island
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- Wells Beach
- Ogunquit Playhouse
- East End Beach
- Long Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Long Sands Beach
- Popham Beach State Park
- Purity Spring Resort
- King Pine Ski Area
- Parsons Beach
- Portland Museum of Art
- Mothers Beach
- Ferry Beach
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Cliff House Beach
- Dunegrass Golf Club
- Palace Playland
- Funtown Splashtown USA
- Laudholm Beach
- West Shore Sandy Beach
- Arundel Beach