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Pet-friendly holiday rentals in Chebeague Island

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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 $136 NZD 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.

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Guest favourite
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.

4.87 out of 5 average rating, 239 reviews
Guest favourite
A charming coastal home is showcased with light-colored siding and a bright blue front door. Surrounding greenery includes tall trees and manicured shrubs. The property is set back from a grassy area, adding to its inviting curb appeal.
Home in Falmouth

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

4.9 out of 5 average rating, 328 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.

4.99 out of 5 average rating, 203 reviews
Guest favourite
A cozy living and dining area features comfortable seating, including a pair of light-colored armchairs and a round dining table. Soft lighting illuminates the space, and decorative accents, such as art and plants, create a welcoming atmosphere.
Apartment in Cape Elizabeth

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

4.92 out of 5 average rating, 697 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

4.97 out of 5 average rating, 174 reviews
Top Guest favourite
A serene vista showcases the city skyline reflected in calm waters, framed by lush green grass and trees. The scene captures a tranquil moment, inviting viewers to appreciate the natural beauty and urban blend surrounding the space.
Home in Portland

Top Deck - Portland Property with Views!

Views, Views, Views! 2 huge decks overlooking water and city skyline. This home is adjacent to Payson’s Park – Portland’s largest park. 5-7 min ride to downtown Portland and the Old Port’s fabulous bars and restaurants. The main floor has bedroom with bath, kitchen, and living room. The upstairs has a large bedroom with bath, open room that can be used as 2nd living room or a 3rd/4th bedroom space. Sleeps 10-12. Off street parking 6-8. Large yard. Portland License #STHR-002587-2020

4.92 out of 5 average rating, 304 reviews
Top Guest favourite
An airy living space is highlighted by tall windows that bring in natural light and showcase views of the surrounding trees. A large sectional sofa faces a flat-screen TV, complemented by a wood stove for warmth. A dining area is visible in the background.
Home in Freeport

Waterfront 5 BR Home | On Casco Bay in Freeport

Spacious waterfront 5BR coastal retreat on Harraseeket Cove and South Freeport Harbor, perfect for kayaking, wildlife, and relaxing coastal Maine getaways. Set on 3.5 private wooded acres, the home features fast WiFi, smart TVs, outdoor dining, grills, firepit, kayaks, and peaceful water views throughout the property. Enjoy the tranquility of Maine’s coast while being only 3 minutes from Freeport’s shops, restaurants, breweries, and LLBean, with Wolfe’s Neck Woods State Park nearby.

4.96 out of 5 average rating, 145 reviews
Guest favourite
Home in Peaks Island

Year-Round: Peaceful and Quiet Island Getaway

*Quiet and Peaceful *Easy Portland Access *Sparkling Bathroom Remote Downeast island experience just two hours from Boston ... Renovated home in the tranquil Tolman Heights section of Peaks (the island’s highest point) offers a modern kitchen and sparkling new bathroom. Sleeps 6-plus comfortably in bedrooms all equipped with ceiling fans. Spacious home is a short stroll to the Back Shore, with its dramatic views of Casco Bay and the open ocean. STHR-007313-2025

4.87 out of 5 average rating, 185 reviews
Superhost
A private balcony offers views of tranquil waters and nearby trees. A white chair is positioned against the railing, inviting relaxation while taking in the natural scenery. The landscape includes subtle reflections on the water's surface, enhancing the coastal surroundings.
Home in Yarmouth

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!

4.91 out of 5 average rating, 149 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.

4.98 out of 5 average rating, 240 reviews
Top Guest favourite
An open living area features a light-filled space with high ceilings and large windows. A neutral-colored sofa offers comfortable seating, complemented by a wooden dining table with stools. A contemporary refrigerator and kitchen area are visible, along with decorative elements such as a plant and a flower bouquet.
Home in Freeport

Spacious Costal Home in Freeport, ME

Come enjoy Freeport, Maine in this beautiful home. One mile from the downtown shopping district and the L.L. Bean flagship store. This two family home is being rented as a single family home, giving you the benefit of two kitchens and two living rooms. Perfect for families and groups of friends. The two sides are connected via a door similar to adjoining hotel rooms.

4.96 out of 5 average rating, 208 reviews
Top Guest favourite
A charming cottage is showcased against a backdrop of lush greenery. Large windows reflect natural light, while vibrant flowers and greenery frame the entrance, enhancing the natural setting. The simple design features a light-colored exterior and a cozy, welcoming presence.
Guesthouse in Freeport

Mast Landing Cottage

Keep it simple at this centrally-located newly renovated cottage. Downtown Freeport is only 1.2 miles away for shopping, restaurants, and even the Amtrak! Wolfe's Neck State Park, Mast Landing Audubon Sanctuary, and Winslow Park are also close for miles of hiking and kayaking. Portland is a 20 minute drive and Brunswick/Bowdoin College are only 15 minutes away.

5.0 out of 5 average rating, 108 reviews

Popular amenities for Chebeague Island pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Guest favourite
A charming beach house is surrounded by trees, featuring a light green exterior with white trim. The front porch has steps leading to the entrance, which is framed by large windows. A landscaped yard with shrubs provides a welcoming view.
Home in Phippsburg

Classic Maine, Modern Comfort

4.94 out of 5 average rating, 297 reviews
Guest favourite
Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

4.97 out of 5 average rating, 197 reviews
Guest favourite
A sunlit sunroom features three woven chairs adorned with soft cushions in varying shades of blue. A low wooden table with a vintage checkers board is situated in the center. Sheer white curtains gently drape around the windows, allowing natural light to enter.
Home in Falmouth

Beautiful +Nostalgic + Coastal Maine Cottage

4.85 out of 5 average rating, 230 reviews
Top Guest favourite
An open living area is highlighted by large windows that frame scenic views of the marsh. A modern gas fireplace serves as a focal point, while a light-colored sofa and a small table with a plant create a welcoming ambiance. Bar seating for four extends to the kitchen.
Home in Higgins Beach

Higgins Beach *New* Beach Home & Private Offices

5.0 out of 5 average rating, 115 reviews
Guest favourite
A welcoming covered porch features white rocking chairs and a light blue table, complemented by window shutters painted in a matching hue. An anchor decoration adds a nautical touch, while potted flowers introduce a hint of greenery.
Home in Scarborough

Pine Point Beach Getaway - Steps From the Beach!

4.91 out of 5 average rating, 185 reviews
Top Guest favourite
Home in Old Orchard Beach

OOB Oasis: 6BR Home w/ Private Pool Near Beach

4.95 out of 5 average rating, 155 reviews
Top Guest favourite
An open-concept living area features warm wooden flooring and mid-century style decor. A vibrant orange sofa is positioned opposite a dining table with wooden chairs. Natural light floods in through large windows, and a set of stairs leads to the upper level.
Home in Portland

3 bedroom house in the heart of Portland

4.98 out of 5 average rating, 411 reviews
Top Guest favourite
An aerial view displays a colonial home surrounded by vibrant autumn foliage, set on an expansive lawn. The nearby Kennebunk River curves through the landscape, bordered by trees. The property includes a serene setting with open spaces and distant houses visible among the greenery.
Home in Arundel

Classic, calm river view & centrally located home

4.95 out of 5 average rating, 108 reviews

Pet-friendly home rentals with a pool

Top Guest favourite
Cabin in Norway

Secluded Cabin: Mountain View, Hot Tub + Fireplace

5.0 out of 5 average rating, 103 reviews
Guest favourite
Cabin in Freeport

A-frame w/ towering 18ft glass wall & deck - 15

CleanlinessLocationFamily

4.95 out of 5 average rating, 116 reviews
Guest favourite
Home in Kennebunk

Beach House w/ Heated Pool · Fire Pit · Kennebunk

4.83 out of 5 average rating, 179 reviews
Top Guest favourite
Place to stay in Shapleigh

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

5.0 out of 5 average rating, 140 reviews
Guest favourite
Home in South Thomaston

Large private area, close to Rockland

4.94 out of 5 average rating, 113 reviews
Guest favourite
A welcoming living area features warm wood flooring and natural light from multiple windows. Comfortable seating includes a sofa and chairs arranged around a central table. A ceiling fan provides gentle airflow, while double French doors lead to an outdoor space.
Guest suite in Standish

Steep Falls Escape, river & falls just steps away

4.92 out of 5 average rating, 125 reviews
Guest favourite
A spacious living area features warm wood paneling and a cozy wooden fireplace. Comfortable seating is arranged around a coffee table, and large glass doors allow natural light to fill the room, leading to the scenic outdoors. A ladder provides access to the loft area.
Chalet in Bridgton

Charming Chalet 3 min to SKIING & PVT beach access

4.87 out of 5 average rating, 129 reviews
Guest favourite
A classic beach house is situated amidst lush greenery, featuring a charming wraparound porch. The two-story structure is accentuated by large windows and a balcony above. A clear blue sky complements the inviting landscape, creating a serene setting just steps from the beach.
Home in Kennebunkport

Lovely Beach house in GRB - Heated pool!

4.98 out of 5 average rating, 58 reviews

Private, pet-friendly home rentals

Top Guest favourite
A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.
Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

4.91 out of 5 average rating, 602 reviews
Top Guest favourite
A relaxing outdoor area is shown, featuring several seating options around a fire pit. Two cabins can be seen, with one situated on a hill and the other by the water. A sun umbrella provides shade, surrounded by trees and nature.
Chalet in Standish

Blueberry Hill

4.96 out of 5 average rating, 261 reviews
Guest favourite
The exterior of the cottage features a large screened-in porch framed by tall trees. A pathway leads to the entrance, while colorful shrubs and a pumpkin add seasonal charm. The serene waters of the Sheepscot River are visible in the background.
Cottage in Edgecomb

Charming Cottage With Spectacular Water View

4.97 out of 5 average rating, 381 reviews
Top Guest favourite
The exterior of a rustic mid-century cabin is framed by lush greenery, featuring a screened-in porch and wooden deck. Stairs lead up to the entrance, and natural stone accents create a seamless blend with the surrounding landscape.
Cabin in Boothbay Harbor

Lakeside 3 BR Cabin in Boothbay Harbor

4.98 out of 5 average rating, 284 reviews
Top Guest favourite
A wooden dock extends toward calm water, with a gentle sloping pathway leading down from the boathouse. The clear water reveals stones at the bottom, while green trees frame the picturesque lakeside view.
Guesthouse in New Gloucester

On the water Boathouse!

4.9 out of 5 average rating, 175 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

4.97 out of 5 average rating, 35 reviews
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!

4.99 out of 5 average rating, 76 reviews
Top Guest favourite
A charming two-story house features a white exterior with green accents. Large windows and a balcony enhance the facade, surrounded by well-kept greenery. The front yard is green and expansive with a walkway leading to the entrance, creating an inviting approach.
Home in Yarmouth

Island home w/fireplace, balcony, and water access

4.95 out of 5 average rating, 37 reviews

When is the best time to visit Chebeague Island?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$411 NZD$409 NZD$372 NZD$409 NZD$421 NZD$502 NZD$602 NZD$638 NZD$516 NZD$465 NZD$450 NZD$477 NZD
Avg. temp-4°C-3°C1°C7°C13°C18°C21°C21°C16°C10°C4°C-1°C

Destinations to explore