
Waterfront vacation rentals in Chebeague Island
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Chebeague Island
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Chebeague Island waterfront rentals
Waterfront apartment rentals

62 Views
Great host, quick to respond to questions. Nice, clean place with great views. Nicely located near downtown, easily walkable. Would recommend if visiting Portland.

Stunning Royal Richmond 2 Br Apartment Get Away!
This apartment was spacious, quiet and comfortable. Perfect for two couples.

Two-Story, Direct Ocean Views on Eastern Promenade
This spot was perfect for a weekend getaway! The Airbnb was clean with spacious accommodations. The apartment has an amazing view of the ocean. Adilah was great to work with! I would highly recommend this stay!

Beachside Penthouse Paradise on Old Orchard Beach
My family had a great a stay at this Air B&B! Peaceful, scenic, and clean. This was exactly what we were looking for and more.

Beautiful Kettle Cove Apt Steps to Beaches
Loved staying here! It's a very short walk to Kettle Cove State Park and Crescent Beach. Cape Elizabeth is a charming, quiet little town. If you're looking for a peaceful relaxing getaway spot, this is it. You'll feel right at home. Plus the hosts are very responsive and friendly. I'm already thinking about when I can return!

🌹Lovely 3Bed-2Flrs✌🏼Free Wine🍷Portsmouth-UNH-Dover
Cozy, clean apartment within walking distance to shops and restaurants. Wine and toiletries were an extra nice extra touch! Great communication!

Marsh Views#3:Cozy/quiet spot on a preserve&river
Great clean place in Kennebunkport. Friendly, helpful and responsive host. Beautiful views of marshes with outdoor activities to enjoy! Will definitely stay here again!

Falmouth Waterfront Carriage House Apt
I have stayed at Anne’s place many times. Anne and her husband are always very nice and friendly. The apartment is spotless, comfortable and you can’t beat the location, just up the hill from charming Falmouth Town Landing and beach and an easy drive to downtown Portland.
Waterfront house rentals

Lakehouse with 100ft of private waterfront
My wife and I spent our first year anniversary in this wonderful home. We had a great time enjoying the fall colors and over looking the beautiful pond, especially in the morning as the fog broke. Within 15 minutes there were several grocery shopping options, restaurants, and breweries. Perfect balance of being in a quiet setting but having amenities nearby. Would recommend and hope to go back next autumn!

Authentic Maine Harbor 5 Bedroom Home
The house was exactly what we were looking for: relaxing with great views. The marina with fresh seafood within walking distance was icing on the cake.

5Bed- Hot Tub - Sauna-Pool Table -Lake Front, Pets
We had a great, low key girls weekend at Alanna’s place. The hot tub was great for soaking in, and right off the deck. We brought our snowshoes and enjoyed snowshoeing down to the lake and around the property. The tvs in the living room felt a bit over powering, but we figured out how to put two to sleep so we could just listen to music on the third.

New Listing! Waterfront Round Pond Home
What an amazing spot! My family and I enjoyed mornings on the dock, watching spectacular sunrises and daily sightings of bald eagles. The walk down to the dock was lined nicely with stone steps and once on the dock it was hard to leave. The three kayaks allowed us to explore the coastline and although the shoreline was rocky, we enjoyed a dip in the cool September waters. The house was perfectly decorated and equipped with everything and anything needed. Lisa was great to work with, quick to answer any questions and accommodating with requests. The beds were extremely comfortable and the view of the sunrise each morning, priceless. The location was perfect, within minutes from a venue where we were attending a wedding and a few restaurants, although we hated to leave the house. I would highly recommend staying at this beautiful home that slept seven of us comfortably. If you're looking for a peaceful spot with stunning views, this place is perfect. We would love to visit again.

Quiet Lake House
We had an awesome stay at this cozy, comfortable cottage—perfect for two families after a full day on the slopes. Every afternoon, we came back to the quiet and warmth of the cabin, made great meals in the super-cute kitchen, built a fire in the wood stove, and played board games around the big table. The kids loved the bunk room (especially having their own book lights!), and everything was easy to find and use. The shower was great, the space was inviting and there were many thoughtful touches such as plenty of hooks for hanging ski gear! We really appreciated how the family updated the cabin while keeping its historic charm. Such a great spot—would absolutely stay again! Thanks for making us feel so welcomed and comfortable!

2 BR Waterfront house with stunning view.
This was a really nice house on a beautiful lake. The beds were comfortable and there were enough to accommodate us. It was very clean and easy to enjoy your stay. We really enjoyed our stay.

Secluded Lakehouse/2 private docks*Hottub*big yard
We had a wonderful stay at this home for a mother daughter weekend end of March. Great location for each of us coming from different states in New England. The home was very clean, each of us commented on how comfortable the beds were, also loved the good quality linens. The huge dining table was unique for a rental and was awesome for sharing meals and doing arts & crafts. Lots of space and seating in the living room as well. Highly recommend staying here!

Charming 4 bedroom lake front, with private beach
Amazing play for a family vacation. My little one loved the beach area and all the toys.
Waterfront condo rentals

Rising Tide at Long Sands Beach!
We loved our stay! CONVENIENT!! Perfect for a small family or couple. Right across the street from the beach. Two lovely restaurants right next door, the general store for quick snacks. Walk to the town, park, arcade. The beach was lovely and the tide never came in too close! The rental was very clean, had everything you would need. View and sunrise were amazing. Allee was very responsive! Would definitely come back with my family!

Luxury Beach Front Condo! Prime Location!
The place was beautiful and clean with a great balcony! Access to beach was so easy and so convenient. Thank you for hosting us !!

Don’t miss out, book for Fall NOW!
This AirBnB was a perfect winter vacation escape. It had everything we needed for our two families. The kitchen was so well stocked and we were never without. Great set up. My 5 year old begged to live there forever! We can't wait to come back!

Oceanfront Condo with Awesome Views
This is the perfect place! Everything is very clean, and nothing missing! Kevin is very nice. He was good tips. I've always dreamed of coming to OOB in the winter and really enjoyed the experience! Loved our stay. With its location and double patios, the views are splendid! For lovers of the sound of the waves, the view of the sea, sunrises, long walks to the beach… this is the place!

Two-Bedroom Condo on the Wells/Ogunquit town-line
Had a wonderful stay at Christophers place. He is a great host, always responsive with clear instructions. Place was peaceful, private and is exactly same as it was in the pictures. Will come soon!

The Brunswick
The location is amazing. The view is amazing as shown in the pictures. The apartment was actually pretty quiet, we couldn’t hear anyone in other units and little to no noise from the beach or bar below, though we stayed in the off-season. The balcony is huge and plenty of seating options and the living room is spacious and lots of seating. We had two young kids with us and we all had a great time. Would stay again.

NEW Beachside Wells Beach Condo with Pool
The Wells Beach condo was very comfortable and clean. It was off season so it was pleasantly quiet. It is very close to a great beach with a long stretch to walk and great for swimming and sunbathing in the good weather. There was a pool right outside the condo door which would be super convenient in the warm weather. The condo is well maintained and the ability to walk across the street to the beach is a great benefit. Plus there are restaurants and shops close by,

Rustic Willard Beach condo ten mins from Old Port!
Dave was a very responsive host and his property was exactly what he described. The location was very good to visit downtown Portland. At last, we loved the bakery right in front!
Quick stats about waterfront rentals in Chebeague Island
Total rentals
60 properties
Nightly prices starting at
$120 before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Ogunquit Beach
- Wells Beach
- Sebago Lake
- Scarborough Beach
- York Harbor Beach
- Ogunquit Playhouse
- Long Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Long Sands Beach
- Popham Beach State Park
- Purity Spring Resort
- East End Beach
- King Pine Ski Area
- Palace Playland
- Dunegrass Golf Club
- Pemaquid Beach
- Middle Beach
- Parsons Beach
- Mothers Beach
- Ferry Beach
- Laudholm Beach
- Portland Museum of Art
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