Cottage holiday rentals in Chebeague Island

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Popular amenities for Chebeague Island cottage rentals

Cottage rentals with a hot tub

Top Guest favourite
Cottage in Wells
4.97 out of 5 average rating, 61 reviews

Freshly Renovated, Family-Friendly Coastal Cottage

TaylorRating, 5 stars9 months ago
A gem of an Airbnb! The hosts truly thought of everything and this was the perfect place to stay with two young kids; in fact, my son loved the bunkbed and toys so much he refused to go to bed every night! From the tonies box and kids toys, to all the beach and baby gear, there wasn’t one thing they lacked. The place was clean and organized and felt so cozy. I highly highly recommend this place, especially for families! The hosts were so friendly and accommodating as well.
Superhost
Cottage in Limerick
4.78 out of 5 average rating, 68 reviews

Maine Lakehouse, 3 Bedrooms, 2 baths, waterfront

ShannonRating, 5 stars6 days ago
A great spot tucked away!! House was cute and as shown in the pictures, is right on the water and has some great views! It rained the majority of the time we were there so didn’t get to take advantage of all the outdoor amenities, but would have if better weather! Host was very friendly, communicative and responsive!
Guest favourite
Cottage in Kennebunk
4.92 out of 5 average rating, 25 reviews

Fully Renovated/4min to K-port/HotTub/Game Room

Maverick & MichelleRating, 5 stars2 weeks ago
Great clean air bnb. Accurately as described.. looks good in photos but even better in-person. Bed was comfortable. Would rent their properties again.
Superhost
Cottage in Casco
4.88 out of 5 average rating, 24 reviews

Waterfront Getaway w/ Private Sandy Beach

RileyRating, 5 stars3 weeks ago
Perfect for what we needed for a weekend getaway. So peaceful and a lot of interesting wildlife. We saw so many different types of birds! The hot tub is spacious and easy to use.
Top Guest favourite
Cottage in Camden
5 out of 5 average rating, 37 reviews

Megunticook Retreat

DebraRating, 5 stars2 weeks ago
We’ve stayed in a lot of Airbnbs across the country and I’m not exaggerating when I say that Lydia’s place was one of the cleanest and most well-maintained homes that we’ve been in. The property and scenery are breathtaking. The numbers of birds and chipmunks that entertained us while we sat on the back deck was surprising. We ate all of our meals with the exception of lunches at the cabin and had everything we needed to prep and cook our food. This trip was all about relaxing and Lydia’s home was everything we needed.
Guest favourite
Cottage in Wells
4.93 out of 5 average rating, 44 reviews

Cottage in Wells Maine

KaylaRating, 5 stars2 weeks ago
We had a wonderful stay here and highly recommend it! The location is great, as it’s close to plenty of restaurants and stores. We were even able to walk to get breakfast and dinner. The space itself was much larger than we expected and very clean. The kitchen had everything we needed and we even had snacks, waters, and coffee left for us! The highlight for my 2 year old was the pirate ship playground. We also loved having access to picnic tables. We got takeout and enjoyed eating outdoors. We did not use the outside grill but that is a great addition and we would have used if we stayed longer. The host was very helpful and accommodating. They offered early check in and check out and gave very clear instructions on how to get in. I would not hesitate to return in the future!
Top Guest favourite
Cottage in Cape Neddick
4.98 out of 5 average rating, 197 reviews

Adorable cottage by Shorts Sands Beach

KatieRating, 5 stars4 days ago
Camille’s place is fantastic! Great location and it’s so clean and well decorated. Camille is so fast to communicate and is very accommodating. We’ve stayed many times and look forward to returning again.
Guest favourite
Cottage in Wells
4.94 out of 5 average rating, 148 reviews

Cozy Cottage with Ocean Views, Wells Maine

JanaRating, 5 stars6 months ago
The cottage is spotless, well-stocked and conveniently located for day trips in any direction. This is our 4th year staying at this lovely cottage for a pre-holidays getaway. We look forward to keeping this annual tradition!

Pet-friendly cottage rentals

Top Guest favourite
Cottage in Waterford
4.99 out of 5 average rating, 144 reviews

Tall Pines Hideaway

JessRating, 5 stars6 days ago
Beatiful cabin on the water, thoughtfully decorated. I loved the layout, plenty of seating areas and lovely decor. There is only one small bathroom which may be an issue with more than 2 or 3 guests, but worked out perfectly for us. We saw deer twice when driving down the trail to the house which was exciting! Loved using the firepit outside. The only bummer was that the dock wasn’t in the water yet. I still managed to use the kayak but would not advise attempting without the dock lol. Wonderful host, David was very responsive and had a nice bottle of wine waiting for us on our arrival. Would 100% come back
Guest favourite
Cottage in Woolwich
4.92 out of 5 average rating, 182 reviews

Pet Friendly Audubon Bring Your Fishing Gear!

LisaRating, 5 stars1 week ago
Tammy describes her sweet cottage perfectly. Water views are spectacular with options to fish off the dock, sit in the backyard to warm up or sit on the bluff to cool off. It was perfect for this girl and her dog to re-set in solitude. Most places on the water have sensitive septic as described so you want to consider that if there are more than two guests. I enjoyed my endless walks on Popham beach (no dogs 4/1-10/1)) and was thrilled to be there in the off season. I barely saw anyone! Reid State Park was also spectacular and more opportunity to walk my dog on the trails. Tick season is a bit of an adjustment every year but not a problem if you prepare yourself and your furry friends. A perfect place for a great book, wandering around historic Bath, and easy meal prep. I stayed 2 weeks and appreciated all the thought Tammy put into anticipating what a traveler might need.
Superhost
Cottage in Lyman
4.82 out of 5 average rating, 102 reviews

RK North : All season Waterfront cottage with dock

EricRating, 5 stars1 week ago
A Perfect Waterfront Escape – 5 Stars My wife and I had an unforgettable stay at RK North Waterfront Cottage. From the moment we arrived, we were welcomed by breathtaking views, fresh coastal air, and a sense of peaceful seclusion that made this trip truly special. The cottage itself was spotless, beautifully maintained, and tastefully decorated with cozy touches that made it feel like a true home away from home. We especially loved the spacious deck overlooking the water — perfect for morning coffee or evening wine while watching the sunset. The hosts were thoughtful and responsive, ensuring we had everything we needed without ever being intrusive. Whether it was relaxing by the fire pit, walking along the shore, or just enjoying the tranquility of the surroundings, every moment felt effortless and restorative. If you’re looking for a quiet getaway with charm, comfort, and stunning waterfront views, this is the place. We’re already planning our next visit. — Eric & Juliet DiNoto
Guest favourite
Cottage in Friendship
4.91 out of 5 average rating, 266 reviews

Our charming,oceanfront, Bradford point cottage

EricaRating, 5 stars5 days ago
We had a lovely stay at Jeff's place in Friendship and appreciated all the thoughtful touches there. It was wonderful taking the kayaks out to explore the surrounding islands. I would also recommend the lobster rolls nearby at the Jameson Point restaurant.
Guest favourite
Cottage in Bridgton
4.91 out of 5 average rating, 183 reviews

True Maine Artist Cottage with Outdoor Shower

JimmyRating, 5 stars6 days ago
We had such a great time staying at Emily's awesome retreat. It was our first mini-vacation with our dog and we were looking for some peaceful, wide open space to let her roam free. We absolutely got that with this home and thoroughly enjoyed the town, as well. Emily was super responsive whenever we did have a question and provided us with a great list of places to check out around town. Would absolutely stay again. Thanks!
Top Guest favourite
Cottage in South Bristol
4.97 out of 5 average rating, 104 reviews

Hermit Thrush House

DemetriaRating, 5 stars2 days ago
Barbara place is awesome for a couple plus I child nice quiet area very clean and it private. Barbara is a great host you will love this spot it feels like home we will be back
Guest favourite
Cottage in Wiscasset
4.88 out of 5 average rating, 274 reviews

Waterscape Cottage - private waterfront

SophieRating, 5 stars1 week ago
We loved staying at Ann's place! It was exactly what we wanted, close to town and to lots of activities but also felt remote and in a really gorgeous location. Great, rustic spot.
Guest favourite
Cottage in Edgecomb
4.91 out of 5 average rating, 150 reviews

Spectacular Water View Cottage

ChristaRating, 5 stars1 month ago
Enjoyed staying at this cottage at Sheepscot Village. Very clean & responsive host. Look forward to staying again.

Private cottage rentals

Top Guest favourite
Cottage in Harpswell
4.96 out of 5 average rating, 47 reviews

Old fashion neighborhood near the water.

CharlyneRating, 5 stars2 days ago
This was my second time staying at the cottage, and I’m looking forward to going back .
Guest favourite
Cottage in South Bristol
4.99 out of 5 average rating, 118 reviews

Cottage, mooring, and wharf in a fishing village

NickRating, 5 stars7 months ago
Very unique home, beautiful views, quiet, everything we were looking for. We ordered Lobsters from across the street (super nice people) in the morning and they had them ready for pick up at dinner.
Top Guest favourite
Cottage in Falmouth
5 out of 5 average rating, 44 reviews

Cobb Cottage: Lake Beachfront Fri-Fri Jul-Aug

ZephyrRating, 5 stars4 days ago
Great cottage right on the lake! Kayaks were great to take out and explore the lake and see wildlife as well. The cottage is spacious and comfortable. The kitchen is large and well appointed for any cooking you may want to do. Grill and plenty of beach chair/ towels available as well. Adam is extremely responsive and I highly recommend. The place is quite peaceful though the lake gets pretty busy on the weekends with boats but not in an obnoxious way. Loved sipping coffee and reading on the dock each morning. Will definitely book again!
Top Guest favourite
Cottage in Cornish
5 out of 5 average rating, 69 reviews

The Lil'house - A Mountain Top Modern Cottage

MatthewRating, 5 stars7 months ago
Dan and Jane have a beautiful home. They were extremely kind and I can’t thank them enough for allowing me and the kids to meet their horses. It is a wonderful property on a serene landscape. The pictures don’t do it justice. We will certainly be back.
Top Guest favourite
Cottage in Georgetown
4.98 out of 5 average rating, 42 reviews

Serene Coveside Cottage

DanielRating, 5 stars2 weeks ago
My wife and I stayed at Viktor's place for our honeymoon. As soon as we walked through the door it felt like we were in a second home. We loved using the projector and home theater setup to play Nintendo Switch and watch Netflix. I liked that the bedroom had its own separate A/C unit from the living room. Made it so much easier to set the temperature during the day and evening. The combined washer/dryer unit worked great and didn't have any issues drying our clothes. Nearly every morning we were greeted by neighboring deer who came to feed on the backyard grass. The surrounding area (Georgetown, Bath, and Boothbay Harbor) are really great to find good food, parks, and entertainment nearby. I highly recommend this place. It really is a gem in the middle of the forest.
Top Guest favourite
Cottage in Windham
5 out of 5 average rating, 79 reviews

Romantic waterfront cottage for two in Maine

MackRating, 5 stars3 weeks ago
We stayed at the cottage for a little celebratory getaway. Although the weather only partially complied, we were amazed by the beautiful views that surrounded the cottage. We spent some time exploring the area and there are some spectacular little gems hidden throughout and around Windham. Maryellen and Bryan were so sweet and made sure to make this stay feel a little closer to home. Definitely a “don’t miss” property!
Guest favourite
Cottage in Falmouth Foreside
4.91 out of 5 average rating, 35 reviews

Coastal Cottage in Falmouth Foreside

MarthaRating, 5 stars9 months ago
Amy’s place suited us perfectly — not far from my family in Portland, comfortable accommodation, furnished and decorated with flair, and best of all, a little beach down the street that we visited for our daily swim!
Guest favourite
Cottage in Harpswell
4.95 out of 5 average rating, 64 reviews

Private oceanfront cottage, great views, and float

TimRating, 5 stars2 weeks ago
the stay was nice, the place was clean, match the description, pretty easy to find, and Christine had great communication. very beautiful views, right on the water, kayaking was nice.

Quick stats about cottage rentals in Chebeague Island

  • Total rentals

    50 properties

  • Nightly prices starting at

    $199 NZD before taxes and fees

  • Total number of reviews

    1.2K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore