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.

Are there family-friendly vacation rentals in Chebeague Island?

Chebeague Island has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Vacation rentals in Chebeague Island

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Top-rated vacation rentals in Chebeague Island

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

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Guest favorite

Rental unit in Yarmouth

4.96 out of 5 average rating, 124 reviews

Sweet 1-Bedroom Apartment in Vintage Village Cape

Built roughly 200 years ago, the traditional cape housing this first-floor apartment is located on a hilltop above the Royal River, just steps from restaurants, trails, and waterfront. It's been thoroughly renovated, and features pretty much all the comforts of home—including a full kitchen with dishwasher, a wood-burning fireplace insert, an all-natural mattress (super comfy), and a clawfoot tub-equipped bathroom. Oh, and if you're bringing a third, let me know—and I'll roll in the rollaway.

Guest favorite

Yurt in Chebeague Island

4.98 out of 5 average rating, 134 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Explore island beaches and hidden trails. Cozy warm heater for fall. This yurt is “glampy” inside with leather chairs, log bed. The yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Outdoor fire pit and firewood. Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to the yurt.

Guest favorite

Cabin in Freeport

4.97 out of 5 average rating, 501 reviews

Cozy Cottage-Near Harbor & Park

Bailiwick Cottage is a cozy, private cottage that looks south down Freeport (Harraseeket) Harbor in Freeport, ME. It is a 4 season accommodation that is close to Freeport shopping, Portland eating, and the Adventure Schools of LL Bean. The cottage sits approximately 50 yards from our main house, has its own parking space and patio, and offers the ability to come and go as you wish. We have had 12 honeymoons in the cottage. Freeport Registration # STRR-2022-59

Guest favorite

Cottage in Portland

4.89 out of 5 average rating, 534 reviews

Cozy & Quiet Modern Cottage

Modern studio cottage designed and maintained with sustainability and eco-friendliness in mind, located in a quiet Portland neighborhood only a 7-10 minute drive (and $10 Uber/Lyft ride) from downtown Portland, the Old Port, and all local visitor attractions. The cottage is a mile down the road from the Allagash Brewing complex and is within walking distance (.5 mi) of the restaurants and bars at Morrill's Corner. This is an LBGTQIA- and BIPOC-friendly space.

Superhost

Home in Yarmouth

4.86 out of 5 average rating, 125 reviews

Eagle's Nest on 8 acres next little john preserve

Nestled on 8 acres overlooking Casco Bay, the Eagle's Nest cottage has 1 bedroom and 1 bathroom. Open plan with full-kitchen and living room including a queen-size sofa bed. Located on an island, you're only 20 minutes from downtown Portland and 10 minutes from downtown Yarmouth. Last but not least the cottage is a 5-minute walk from a 23-acre preserve that has numerous scenic viewpoints, tide pools and ledges, and picnic tables. Coastal Maine at its best!

Guest favorite

Guest suite in South Portland

5 out of 5 average rating, 216 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer, and cozy couch for lounging.

Guest favorite

Rental unit in Freeport

4.92 out of 5 average rating, 214 reviews

1000 sq. ft. 1BR+ Apt Close to Town & Nature

This very spacious and light filled apartment has beautiful views of a marsh and the headwaters of the Harraseeket River. It is also across the street from a 100+ acre bird sanctuary. There is a queen bed in the bedroom, a twin in the large living room, and a twin in a small nook under the eaves off of the kitchen. You can put kayaks in across the street and it is a short 20 minute walk into downtown Freeport. Great year-round location.

Guest favorite

Cottage in Yarmouth

4.95 out of 5 average rating, 100 reviews

Buoys on Bates | Private + Stylish Cottage | Maine

Stylish cottage retreat between Portland and Freeport w/ universal EV charging - perfect weekend escape from Boston/NYC. Spotless, modern interior w/ full kitchen, Netflix/AppleTV+, premium Tuft+Needle bed, and W/D. Walk to shops, restaurants, and the scenic Royal River. Easy drives to Maine's iconic beaches, Portland's renowned restaurants, LL Bean flagship, and top-rated Maine Brewing. Your ideal base for coastal Maine adventures.

Guest favorite

Guest suite in Freeport

4.97 out of 5 average rating, 147 reviews

Solar Suite surrounded by Nature

Solar suite on conservation property offers peaceful getaway. Large sitting room furnished with contemporary sofa, reading area, bedroom nook with natural latex Queen mattress on Japanese platform, kitchen island/toaster oven, mini fridge, dishes, silverware, linen napkins (please note this is not a full kitchen for preparing meals) private bath/shower. On the lower level of our home with private entrance. Cedar hot tub available.

Guest favorite

Home in Harpswell

4.98 out of 5 average rating, 196 reviews

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin 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.

Guest favorite

Guesthouse in Cumberland

4.96 out of 5 average rating, 201 reviews

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.

Guest favorite

Home in Yarmouth

4.92 out of 5 average rating, 515 reviews

Beautiful Coastal Maine Getaway

Set back among backdrop of tall pines on Maine's coast is our immaculately clean, and very private 4 bedroom, 2 bath home in Yarmouth. Quiet and secluded, and perfectly located between Portland and Freeport, it's an amazing place to decompress with family and friends. Our home comes complete with absolutely everything you need to enjoy your stay!

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chebeague Island vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

Other great vacation rentals in Chebeague Island

Guest favorite

Home in Freeport

5 out of 5 average rating, 26 reviews

Waterfront Cottage in Freeport

Guest favorite

Rental unit in Boothbay

4.96 out of 5 average rating, 306 reviews

Sunnymeade

Guest favorite

Treehouse in Georgetown

4.98 out of 5 average rating, 422 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Guest favorite

Barn in Freeport

5 out of 5 average rating, 159 reviews

Cozy Maine Barn Hideaway- 2nd Floor Apartment

Guest favorite

Rental unit in Falmouth

4.98 out of 5 average rating, 60 reviews

Sweet 2-story 1910 Bungalow near Portland, Beaches

Superhost

Cottage in Harpswell

4.89 out of 5 average rating, 153 reviews

Classic Maine Cottage - dock, sauna & kayaks

Guest favorite

Guesthouse in Portland

4.95 out of 5 average rating, 300 reviews

Beautiful large studio on the ocean.

Guest favorite

Guesthouse in Freeport

4.98 out of 5 average rating, 45 reviews

Discover Minglewood: A Peaceful Couple's Getaway

Show all

Quick stats about vacation rentals in Chebeague Island

Total rentals
10 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
500 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace

Frequently Asked Questions

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.
Are there family-friendly vacation rentals in Chebeague Island?
Chebeague Island has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Vacation rentals in Chebeague Island

Top-rated vacation rentals in Chebeague Island

Rental unit in Yarmouth

Yurt in Chebeague Island

Cabin in Freeport

Cottage in Portland

Home in Yarmouth

Guest suite in South Portland

Rental unit in Freeport

Cottage in Yarmouth

Guest suite in Freeport

Home in Harpswell

Guesthouse in Cumberland

Home in Yarmouth

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Chebeague Island vacation rentals

Stay near Chebeague Island's top sights

Other great vacation rentals in Chebeague Island

Home in Freeport

Rental unit in Boothbay

Treehouse in Georgetown

Barn in Freeport

Rental unit in Falmouth

Cottage in Harpswell

Guesthouse in Portland

Guesthouse in Freeport

Quick stats about vacation rentals in Chebeague Island

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Wifi availability

Popular amenities

Frequently Asked Questions

Destinations to explore