
Pet-friendly holiday rentals in Chebeague Island
Find and book unique pet-friendly homes on Airbnb
Quick stats about holiday rentals that are pet-friendly in Chebeague Island

Total holiday rentals
Explore 90 holiday rentals in Chebeague Island

Nightly prices starting at
Chebeague Island holiday rentals start at $113 AUD per night before taxes and fees

Verified guest reviews
Over 2,860 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Chebeague Island holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chebeague Island rentals

4.8 Average rating
Chebeague Island stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated pet-friendly home rentals in Chebeague Island
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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.

Mongolian Yurt on Chebeague Island
Experience the magic of an authentic Mongolian yurt. The yurt is exquisitely charming, nestled in a private clearing in the woods. From this central location, explore island beaches and wooded island trails. Outdoor fire pit & firewood. Solar dome fans for summer, heater for cool weather. Solar lights inside and out, beefy battery for electronics. Fast internet. The kitchen is fully equipped for cooking: stovetop, fridge, sink, water. Host will provide transport from the ferry to/from the yurt.

Luxury Year-round Treehouse with private hot tub
The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Portland + Cape Elizabeth + Beaches + luxurious!
Permit210780 •Luxurious 3 rm apt with 1322 5* reviews! Only a mi to the beach & 4.4 mi to Portlnd - Location! •1st flr Great Rm to dine & relax: microwave, fridge, toaster, Keurig, TV, cooktop •2nd flr huge bathrm & bedrm for 2 w/ another sitting rm + a 2nd bdrm w/ 1 Q & 2 twins •More than 2 people? Alter reservation #’s for additional cost •2 people wanting 2 bedrms? Only add a $50 cleaning fee for 2nd bdrm •luxurious furnishings & superior bedding! •I am known for thinking of EvErYtHiNg ;-l

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Higgins Beach *New* Beach Home & Private Offices
Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

Charming Cottage With Spectacular Water View
Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Stone Isle. 8 acres next 2 little john preserve.
Nestled on 8 acres overlooking Casco Bay, the Stone Isle guest house has 2 bedrooms, 1 bathroom and amazing water views. The guest house includes an open plan layout with a full kitchen, living room (with sleeper sofa) and a dining table for 4. Last but not least the guest house 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!

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.

Waterfront Sunrise Cove Cottage
Unwind with spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! This is the perfect home base for a midcoast Maine getaway. The post-and-beam cottage has cozy furnishings and expansive views across a field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river & nights are full of stars. Owners live on property with small dog.

HotTub/5min to K-port, Pet friendly, @anchorunwind
Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."

Cozy storybook A-frame over a stream - 24
The Cozy is a small A-frame cabin that features a wall of glass overlooking beautiful woods with a little stream winding through. The cabin is 11/10 romantic and surprisingly comfortable for such a small space. Outside you have a charming seating area with bistro lights, Adirondack chairs, and a fire pit to enjoy a crackling fire.
Popular amenities for Chebeague Island pet-friendly home rentals
Pet-friendly house rentals

Large Historic 7 Bedroom home with Pool & Hot Tub

Classic, calm river view & centrally located home

Amazing Bay View Home with Hot Tub

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Classic Maine, Modern Comfort

Spacious Costal Home in Freeport, ME

Waterfront 5 BR Home | On Casco Bay in Freeport!

Top Deck - Portland Property with Views!
Pet-friendly home rentals with a pool

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

Large private area, close to Rockland

Beach House w/ Pool · Fire Pit · Kennebunk

Steep Falls Escape, river & falls just steps away

Charming Chalet 3 min to SKIING & PVT beach access

Pool+Hot Tub+Sauna Near Beaches Spa Retreat

Historic Harpswell Cottage, Ocean Views

5 Bedroom Home Pool & Hot Tub
Private, pet-friendly home rentals

Mast Landing Cottage

Large Loft—Walk to Breweries— Coffee Bar—King Bed

Completely Private Guest Suite Near Higgins Beach

Timeless Tides Cottage

Falmouth Waterfront Carriage House Apt

SILVER MOON, a Yurt for All Seasons

Tiny house near the beach!

Maybelle the Tiny Cabin on 100 acres
When is the best time to visit Chebeague Island?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $342 AUD | $340 AUD | $309 AUD | $340 AUD | $350 AUD | $418 AUD | $501 AUD | $531 AUD | $429 AUD | $387 AUD | $374 AUD | $397 AUD |
| Avg. temp | -4°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 21°C | 16°C | 10°C | 4°C | -1°C |
Destinations to explore
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- Rentals with beach access Chebeague Island
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- Pet-friendly rentals Cumberland County
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- Pet-friendly rentals United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Short Sands Beach
- Willard Beach
- York Harbor Beach
- Scarborough Beach
- Footbridge Beach
- Cape Neddick Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- East End Beach
- Gooch's Beach
- Hills Beach
- Fortunes Rocks Beach
- King Pine Ski Area
- Pleasant Mountain Ski Area
- Popham Beach State Park
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Funtown Splashtown USA





