Cottage vacation rentals in Chebeague Island

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Popular amenities for Chebeague Island cottage rentals

Cottage rentals with a hot tub

Guest favorite
Cottage in Searsport
4.93 out of 5 average rating, 103 reviews

Canoe House Bungalow and Spa Retreat ,Searsport

Melinda JRating, 5 stars3 days ago
We had a great two nights here and enjoyed the hot soak and the sauna. It was near many amenities and also felt very removed. Matt’s was attentive without being intrusive, making sure our stay was perfect and the escape we hoped it would be.
Guest favorite
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 favorite
Cottage in Camden
5 out of 5 average rating, 37 reviews

Megunticook Retreat

DebraRating, 5 stars1 week 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 favorite
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 favorite
Cottage in Cape Neddick
4.98 out of 5 average rating, 197 reviews

Adorable cottage by Shorts Sands Beach

KatieRating, 5 stars2 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 favorite
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!
Top guest favorite
Cottage in Camden
4.97 out of 5 average rating, 110 reviews

Owls Head Oceanview Cottage Cedar Hot Tub/Sauna

SarahRating, 5 stars1 month ago
We had an amazing time! The location was perfect and the house was clean, quiet, and peaceful. The hot tub and sauna were an incredible addition, making our stay even more relaxing. Despite all the rain, we were happy to stay indoors, doing puzzles, reading, and playing Scrabble. Mary Jo was so responsive and the warm fire place w plenty of wood added a cozy touch! The pictures really don’t do it justice. We will definitely be back! Thank you so much!

Pet-friendly cottage rentals

Top guest favorite
Cottage in Waterford
4.99 out of 5 average rating, 144 reviews

Tall Pines Hideaway

JessRating, 5 stars4 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 favorite
Cottage in Friendship
4.91 out of 5 average rating, 265 reviews

Our charming,oceanfront, Bradford point cottage

LyndaRating, 5 stars4 days ago
Our stay at Jeff’s cottage was one of the most relaxing since we began our yearly mother-daughter long weekend getaway tradition about 8 years ago. The cottage is rustic, yet cute, comfortable, and clean and the setting is simply beautiful. Some highlights were foggy harbor explorations by kayak, sunset happy hours at the harbor shore, and napping to the sound of the rain on the metal roof. The minimal steps and level front yard made it possible for our mother to enjoy the setting and access the harbor with us. We especially appreciated a freezer full of ice upon our arrival :) We hope to return next June. Highly recommend!
Guest favorite
Cottage in Bridgton
4.91 out of 5 average rating, 183 reviews

True Maine Artist Cottage with Outdoor Shower

JimmyRating, 5 stars4 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 favorite
Cottage in South Bristol
4.97 out of 5 average rating, 103 reviews

Hermit Thrush House

KathiRating, 5 stars7 months ago
The Hermit Thrush House is cozy, charming, and quiet. I slept better than I have in a long time! Everything we needed was there. My mom and I visit MidCoast Maine every fall, and this was our first stay at the Hermit Thrush House. We picked a great place close to all the towns we love to visit. Very nice!
Guest favorite
Cottage in Wiscasset
4.88 out of 5 average rating, 274 reviews

Waterscape Cottage - private waterfront

SophieRating, 5 stars6 days 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 favorite
Cottage in Windham
4.93 out of 5 average rating, 106 reviews

Cozy Cottage on Highland Lake

MeredithRating, 5 stars8 months ago
Perfect little Maine cabin getaway! We enjoyed our stay so much. The cabin was clean, easy to find, and had everything we needed for four people and two dogs. Cannot recommend enough!
Guest favorite
Cottage in Edgecomb
4.91 out of 5 average rating, 149 reviews

Spectacular Water View Cottage

TimRating, 5 stars1 month ago
Cute and cozy for the two of us on a rainy weekend. Excellent view. Quite a bit of road noise from Route 1. Very comfortable bed and living room. Doing a puzzle at the table overlooking the water and exploring the fort. Wiscassett is cute!
Superhost
Cottage in Harpswell
4.91 out of 5 average rating, 205 reviews

H and K Cove View Cottage LLC

CarissaRating, 5 stars1 month ago
Kristen was willing to accommodate our booking short notice, which we really appreciated. The home was beautiful with stunning views! Excellent location, loved the coffee shop a mile away. Thank you!!

Private cottage rentals

Top guest favorite
Cottage in Falmouth
5 out of 5 average rating, 44 reviews

Cobb Cottage: Lake Beachfront Fri-Fri Jul-Aug

ZephyrRating, 5 stars2 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 favorite
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 favorite
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 favorite
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 favorite
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.
Superhost
Cottage in Falmouth
4.7 out of 5 average rating, 148 reviews

Historic Seaside Cottage 5 min from Portland!

NatalieRating, 5 stars1 month ago
We had a wonderful stay in this home! The neighborhood was great, very peaceful, and had amazing views if you enjoy taking walks. It was a very convenient location to get to many local restaurants and things to do!
Top guest favorite
Cottage in Biddeford
5 out of 5 average rating, 32 reviews

Secluded Coastal Home & Cottage 3 Minutes to Beach

AustinRating, 5 stars6 days ago
It was a pleasure to stay at the cottage! Alexis is a great host who provided a beautiful, clean and well put together place for my family to stay. The cottage is private yet close to a variety of places to visit. I highly recommend staying here! My family and I enjoyed our stay and will be considering another visit when vacationing in Maine again.
Top guest favorite
Cottage in Arundel
5 out of 5 average rating, 50 reviews

Adorable cottage, great location

MarekRating, 5 stars3 days ago
Laura’s place is a peaceful retreat away from the crowds of Kennebunk and Saco. We chose the right spot to relax after the festivities of the weekend wedding events. There were thoughtful touches like milk, butter and tea - which made our stay extra enjoyable. We’re only bummed about all the rain so we couldn’t enjoy the delightful deck and fire pit. As long as you’re okay with the occasional traffic and train going by then this place is a real gem! Super clean, super comfy and super thoughtful!

Quick stats about cottage rentals in Chebeague Island

  • Total rentals

    50 properties

  • Nightly prices starting at

    G$25,105 GYD 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