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Holiday houses in Chebeague Island

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Quick stats about holiday rentals in Chebeague Island

  • Total holiday rentals

    Explore 210 holiday rentals in Chebeague Island

  • Nightly prices starting at

    Chebeague Island holiday rentals start at $85 AUD per night before taxes and fees

  • Verified guest reviews

    Over 5,020 verified reviews to help you choose

  • Family-friendly holiday rentals

    160 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 90 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    200 of Chebeague Island holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ and Laptop-friendly workspace across Chebeague Island rentals

  • 4.8 Average rating

    Chebeague Island stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated holiday rentals in Chebeague Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
Cottage in Harpswell

Quaint & Peaceful Designer's Oceanfront Cottage

Coco Cottage is a peaceful, cliffside escape with stunning 180° views of Harpswell Sound. Located at the end of a private road, it’s perfect for a designer’s retreat or family getaway. Three bedrooms—two queens, plus a twin/office combo—make it ideal for remote work or rest. Relax fireside and watch a movie, dine on the patio, read on the dock, or explore the amazing trails, beaches, seafood and sunsets of Harpswell. Enjoy oceanfront tranquility just 15minutes from Bowdoin College and Brunswick.

LocationFamilyAccess

4.86 out of 5 average rating, 242 reviews
Top Guest favourite
Home in Freeport

Mermaid's Chair | Private Beach | Hot Tub

*Please note: The hot tub is unavailable from October 27 through April. The booking guest must be at least 25 years old. This classic 1939 Maine camp sits directly on Casco Bay, offering a private dock, sweeping water views, and a saltwater hot tub, all on a quiet road. Properties like this don't come around often, and once you arrive, you’ll understand why. The dock places you right on the water, with one boat slip available for guests. Wolfe’s Neck State Park and Wolfe’s Neck Farm are nearby.

LocationValueAccuracy

4.95 out of 5 average rating, 20 reviews
Top Guest favourite
A wooden deck leads to the entrance of the yurt, featuring two green Adirondack chairs flanking the doors. The surroundings are wooded, with a carpet of forest floor visible and trees providing a natural backdrop.
Yurt in Chebeague Island

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking: fridge, stovetop, sink, water, firepit & firewood. Outdoor shower. WiFi . Cozy heater for cool spring nights. Ferry options on Casco Bay Lines or CTC Ferry. Host provides transport to/from ferry to the yurt.

LocationValueOutdoor spaces

4.99 out of 5 average rating, 206 reviews
Top Guest favourite
A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.
Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

You will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

FamilyValueWalkability

4.96 out of 5 average rating, 179 reviews
Top Guest favourite
A dining table is set with a bowl of fresh salad, complemented by a glass of red wine. In the background, the sun sets over the water, casting a warm golden light through large windows that frame the peaceful waterfront view.
Home in Harpswell

Sunset Stunner w/summer dock

Relax with the family at this peaceful place to stay. This cozy waterfront home offers a tranquil escape with breathtaking ocean sunset views that paint the sky each evening. Lots of windows and open concept living area provide uninterrupted vistas of the water, allowing golden light to flood the space. The wrap around deck just steps from the water's edge is an ideal spot for morning coffee or evening dinners as the sun dips below the horizon. This charming home blends comfort and nature.

FamilyLocationBathroom

4.97 out of 5 average rating, 38 reviews
Top Guest favourite
A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.
Cottage in Brunswick

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax with ocean views, warm up in the sauna or take a refreshing dip. Our cottage is part of Gurnet Village, an over 100-year-old working lobstering & oyster farming property on historic Route 24, between Brunswick & Harpswell. Expect boats, workers, road traffic, gear, and the occasional sounds & smells of a real Maine working waterfront. All rooms have ocean views, with access to the tidal beach & floating dock (May-Dec).

LocationValueAccuracy

5.0 out of 5 average rating, 226 reviews
Top Guest favourite
Treehouse in Pownal

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

ValueFamilyHiking

4.99 out of 5 average rating, 199 reviews
Top Guest favourite
A bright hallway leads into the living space, featuring light wood flooring and white walls. A dining area is seen to the left with a small table and chair, while decorative elements, including potted plants and books, add character to the space.
Apartment in Peaks Island

Peaks Island Master Bedroom Suite

Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

LocationFamilyBackyard

4.99 out of 5 average rating, 234 reviews
Top Guest favourite
A large window frames the ocean view, where waves gently roll towards rocky outcrops. A cozy seating area, featuring a leather sofa and a wooden coffee table, is positioned to allow for a serene observation of the changing tides.
Home in Cape Elizabeth

"Periwinkle" ~ a Charming Oceanfront Cottage

Breath taking views await you at Periwinkle, a charming cottage by the sea. Located in a private community where you’ll enjoy a common beach/cove and a beautiful stroll out onto the point where you can enjoy the sun rises and sunsets … The cottage sits on its own little private cove where you can hunt for sea glass! There are long sandy beaches nearby for strolling and swimming and plenty to do and see in the Portland area, just 5 miles or so from the cottage!

LocationFamilyDecor

5.0 out of 5 average rating, 40 reviews
Top Guest favourite
The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.
Cabin in Freeport

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for couples, small families, or a getaway with friends, our signature A-frame features soaring ceilings, oversized windows, a cozy gas fireplace, and thoughtfully designed interiors. • This cozy 1,100-square-foot space sleeps four in two bedrooms—one King and one Queen—with a shared bathroom. • 7 minutes to downtown Freeport. • Proud to be ranked in the top 1% of eligible homes and recognized as a Guest Favorite on Airbnb.

ValueLocationCheck-in

5.0 out of 5 average rating, 155 reviews
Top Guest favourite
A well-maintained cottage is positioned beside a tranquil body of water, surrounded by lush greenery. A spacious lawn is visible in the foreground, showcasing an outdoor seating area with a patio umbrella. The scenic view of the water complements the serene setting.
Home in Harpswell

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove,a tidal cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.

FamilyLocationQuiet

4.98 out of 5 average rating, 244 reviews
Top Guest favourite
Home in Harpswell

Oceanfront Cottage w/ Wharf & Kayaks – Harpswell

Oceanfront cottage on tranquil Basin Cove with a wide private wharf, direct water access, and kayaks. This thoughtfully designed 2BR home features vaulted ceilings, open-concept living, and stunning sunset views. Swim, launch a kayak, or unwind on the deck overlooking the water. Minutes to Mitchell Field Beach, Dolphin Marina, and some of Harpswell’s best seafood and coastal trails.

FamilyLocationCondition

5.0 out of 5 average rating, 26 reviews

Popular amenities for Chebeague Island holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near Chebeague Island's top sights

Casco Bay

7 locals recommend

Land's End Gift Shop

62 locals recommend

Bailey Island Bridge

17 locals recommend

Eagle Island

10 locals recommend

Cliff Island, Maine

8 locals recommend

Mackerel Cove

5 locals recommend

Other great holiday rentals in Chebeague Island

Guest favourite
A spacious house with large glass windows is featured, set against a colorful sunset sky. A wide deck extends around the home, with black outdoor furniture positioned for views. The structure is framed by trees and a grassy area, providing a serene atmosphere.
Home in Long Island

Whole house on a great island in Casco Bay!

LocationFamilyComfort

4.99 out of 5 average rating, 76 reviews
Top Guest favourite
A scenic view of a tranquil waterway reflects soft pink and orange hues from the sky at sunset. Rocky outcrops and patches of greenery frame the serene water, creating a peaceful coastal atmosphere.
Home in Harpswell

Little Harbor Cottage

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 14 reviews
Superhost
Cabin in Harpswell

Beautiful log home on ocean with large deck & yard

LocationFamilyCheckout

4.93 out of 5 average rating, 14 reviews
Top Guest favourite
A cottage is situated at the water's edge, surrounded by lush green grass and bushes. A calm body of water extends in the background, creating a serene environment. The landscape features trees lining the shoreline, enhancing the tranquil atmosphere.
Cottage in Phippsburg

Water's Edge Cottage in Phippsburg, Maine

FamilyLocationCondition

4.99 out of 5 average rating, 92 reviews
Guest favourite
A modern kitchen is highlighted, featuring wooden beams along the ceiling. A spacious island is positioned at the center, accompanied by two wooden stools. White cabinetry contrasts with dark lower cabinets, while large windows allow natural light to brighten the space.
Apartment in Harpswell

Bird Watching Paradise Harpswell

FamilyLocationCleanliness

4.97 out of 5 average rating, 37 reviews
Top Guest favourite
Aerial view of a cottage nestled among lush green trees, with a panoramic view of Casco Bay and its islands beyond. The spacious yard is bordered by natural foliage, providing a serene backdrop for the waterfront property.
Home in Freeport

Waterfront Cottage in Freeport

FamilyLocationNearby

5.0 out of 5 average rating, 93 reviews
Top Guest favourite
The exterior of the country home features multiple stories with a mix of blue siding and a stone chimney. A screened porch is visible, along with outdoor seating on the deck. Lush gardens and trees surround the property, providing a serene backdrop against the water.
Home in Freeport

Spectacular Oceanfront Home w/ Private Cove

FamilyLocationParks

4.97 out of 5 average rating, 61 reviews
Guest favourite
Home in Cape Elizabeth

Walk the beach or watch the tide from "Boatyard"

FamilyLocationNearby

5.0 out of 5 average rating, 20 reviews

When is the best time to visit Chebeague Island?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$382 AUD$382 AUD$341 AUD$314 AUD$320 AUD$405 AUD$446 AUD$451 AUD$391 AUD$353 AUD$327 AUD$355 AUD
Avg. temp-4°C-3°C1°C7°C13°C18°C21°C21°C16°C10°C4°C-1°C

Frequently Asked Questions

  • What types of vacation rentals are available in Chebeague Island?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Chebeague Island. From over 120 house rentals to over 50 cottage rentals, we've got you covered.

  • Are there pet-friendly vacation rentals in Chebeague Island?

    Four-legged friends are welcome in Chebeague Island. Choose from more than 90 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Chebeague Island?

    Yes! Work meets play with ease at over 90 vacation rentals in Chebeague Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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.

  • How much does it cost to stay in cottage rentals in Chebeague Island?

    Experience the best of Chebeague Island with our cottage rentals, starting at about $170 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 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.

  • 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.

  • 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.

Destinations to explore