Chebeague Island island rentals

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Popular amenities for Chebeague Island vacation rentals

Stay near Chebeague Island's top sights

Chebeague Island Inn12 locals recommend
Littlejohn Island Preserve7 locals recommend
Slow Bell Cafe5 locals recommend
Doughty's Island Market4 locals recommend
Great Chebeague Golf Club3 locals recommend
The Niblic & Gallery3 locals recommend

Chebeague Island vacation rentals

Superhost
Cottage in Windham
4.91 out of 5 average rating, 85 reviews

Tranquil waterfront cottage

Jo-AnnRating, 5 stars6 months ago
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.
Guest favorite
Home in Ogunquit
4.95 out of 5 average rating, 73 reviews

Opening May 16th

MaryRating, 5 stars6 months ago
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.
Guest favorite
Condo in Old Orchard Beach
4.91 out of 5 average rating, 416 reviews

Luxury Beach Front Condo! Prime Location!

DebbieRating, 5 stars2 weeks ago
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!
Guest favorite
Home in Old Orchard Beach
4.98 out of 5 average rating, 80 reviews

Faith Lane with community pool

MeghanRating, 5 stars7 months ago
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!
Superhost
Home in Old Orchard Beach
4.84 out of 5 average rating, 55 reviews

Summer Vacation Rental with 3 beds/2 bath

CathyRating, 5 stars7 months ago
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.
Guest favorite
Condo in Kennebunk
4.89 out of 5 average rating, 204 reviews

Over 1000 Five Star Reviews! Walk to Dock Square !

AshleyRating, 5 stars2 weeks ago
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!
Superhost
Cottage in Old Orchard Beach
4.92 out of 5 average rating, 59 reviews

15A -5 Min Walk to Beach&Pier. Quaint Cottage

KaitlynRating, 5 stars8 months ago
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!!
Superhost
Townhouse in Old Orchard Beach
4.89 out of 5 average rating, 9 reviews

Unit 3 Getaway - Perfect for Families!

DanielleRating, 5 stars8 months ago
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

Guest favorite
Home in Scarborough
4.93 out of 5 average rating, 58 reviews

Gorgeous 4 BR home with HOT TUB

Elizabeth AnnRating, 5 stars1 week ago
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!
Guest favorite
Home in Limerick
4.93 out of 5 average rating, 121 reviews

Lakefront Getaway

MarieRating, 5 stars4 days ago
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!
Guest favorite
Cabin in Greenwood
4.92 out of 5 average rating, 13 reviews

All seasons Lake House next to ski areas

GeorgeRating, 5 stars6 months ago
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!
Superhost
Home in Newcastle
4.91 out of 5 average rating, 32 reviews

Spring into the season eating lobsters w/friends

MarceloRating, 5 stars7 months ago
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
Top guest favorite
Home in Gray
4.97 out of 5 average rating, 63 reviews

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars3 months ago
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.
Guest favorite
Home in Kennebunk
4.95 out of 5 average rating, 151 reviews

Quiet cozy cottage close to restaurants, beach

MikeRating, 5 stars6 months ago
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.
Top guest favorite
Home in Bath
5 out of 5 average rating, 101 reviews

Waterfront Farmhouse with Modern Flair!

Tony & KellyRating, 5 stars2 months ago
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.
Guest favorite
Cabin in West Paris
4.94 out of 5 average rating, 107 reviews

Cabin on the hill!

AdrienneRating, 5 stars3 weeks ago
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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