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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 €70 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 & child-friendly amenities

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    80 of Chebeague Island holiday rentals include wifi 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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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.

4.86 out of 5 average rating, 242 reviews
Top guest favourite
A hobbit house is nestled among lush green trees, with a sloping earth-covered roof adorned with grass and ferns. The rounded front features a large window framed in white, complemented by a natural stone border, emphasizing the home's connection with its woodland surroundings.
Earthen home in Sanford

Luxury Year-round Hobbit House w/ private hot tub

Fern Hollow 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.

4.92 out of 5 average rating, 132 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, 331 reviews
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, 305 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, 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

4.96 out of 5 average rating, 179 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.
Flat 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, 700 reviews
Top guest favourite
A serene waterfront scene captures calm waters dotted with boats gently bobbing in the harbor. Rocky shores lead to lush greenery in the background, with a clear blue sky above, creating an inviting coastal atmosphere in this Maine setting.
Flat in Falmouth

Falmouth Waterfront Carriage House Apt

Waterviews! This 1 bedroom apt has a new “purple”mattress, above our detached garage in classic Maine waterfront neighborhood. Next door to the iconic Town Landing Market and Town Landing pier/beach. In beautiful Falmouth Foreside neighborhood. Walkable to Dockside Restaurant and marina, and 10 minute drive or bus to downtown Portland. 20 minute drive to Freeport shopping. We only accept well- behaved and house- trained dogs, no other pets are allowed for a fee of $75.00 per dog per stay.

4.97 out of 5 average rating, 200 reviews
Top guest favourite
A cozy living area is viewed through large glass sliding doors. A wooden coffee table is placed in front of a dark seating area, complemented by two plush pillows. A colorful piece of wall art adds vibrancy to the light-toned walls, enhanced by natural light from the outdoors.
Cabin in Georgetown

Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

4.99 out of 5 average rating, 237 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, 147 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, 244 reviews
Top guest favourite
Home in Georgetown

Cottage on Todd Bay

Autumn is nearly here, and the maples are turning red along the road down from Bath. Days are warm but crisp, and nights are chilly; our guests on Todd Bay have begun building evening fires in the wood stove. We still have a few more available nights in October for fall getaways -- and we're starting to look ahead to May and the 2027 season!

4.98 out of 5 average rating, 157 reviews

Popular amenities for Chebeague Island pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

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 bright living area features a wooden floor and a cozy, gray sofa. A blue writing desk is positioned beside a window, adorned with decorative bookshelves and plants. A vintage-style wood stove is set against a brick wall, with warm light enhancing the inviting atmosphere.
Home in Freeport

Charming Historic Freeport House

4.89 out of 5 average rating, 114 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

4.96 out of 5 average rating, 210 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.

4.9 out of 5 average rating, 150 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, 186 reviews
Guest favourite
Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

4.98 out of 5 average rating, 200 reviews
Guest favourite
Home in Peaks Island

Year-Round: Peaceful and Quiet Island Getaway

4.87 out of 5 average rating, 186 reviews
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, 300 reviews

Pet-friendly home rentals with a pool

Guest favourite
The modern cabin features a sleek design surrounded by lush greenery. Soft bistro lights create a warm glow, illuminating the outdoor seating area with two Adirondack chairs. The deck can be seen in the background, enhancing the inviting atmosphere of the natural setting.
Cabin in Freeport

Romantic hideaway cabin w/ access to spa - 26

4.96 out of 5 average rating, 125 reviews
Top guest favourite
Place to stay in Shapleigh

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

5.0 out of 5 average rating, 145 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
Home in South Thomaston

Large private area, close to Rockland

4.94 out of 5 average rating, 117 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, 130 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, 59 reviews
Guest favourite
A spacious loft area with a vaulted ceiling features large triangular windows that provide expansive views of the surrounding landscape. Natural wood accents enhance the warmth of the space, creating a bright and airy atmosphere complemented by an inviting seating arrangement below.
Cabin in Bethel

POOL+Hot tub+6Private Acres+15 min to Sunday River

4.95 out of 5 average rating, 97 reviews
Guest favourite
The turn-of-the-century cottage is framed by manicured bushes and lush green grass. A spacious front porch features large windows for natural light. The distinct shingled facade and gabled roof are complemented by a mix of trees in the background, showcasing a charming coastal aesthetic.
Cottage in Harpswell

Historic Harpswell Cottage, Ocean Views

4.86 out of 5 average rating, 7 reviews

Private, pet-friendly home rentals

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.
Guest house in Freeport

Mast Landing Cottage

4.99 out of 5 average rating, 113 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, 290 reviews
Top guest favourite
The exterior of a Victorian farmhouse is showcased, featuring classic white siding and multiple large windows. Lush green trees frame the house, while vibrant pink and purple flowers add color to the front yard. A covered porch invites relaxation.
Flat in Lisbon Falls

Charming Victorian farmhouse 1880's bedrooms-2

4.94 out of 5 average rating, 558 reviews
Guest favourite
Flat in Phippsburg

Popham Beach, Small Point, Phippsburg, year round

4.82 out of 5 average rating, 112 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, 389 reviews
Superhost
A spacious dining area is highlighted by a wooden table surrounded by white chairs. A staircase with wooden railings leads to the upper level. Natural light fills the room through multiple windows, enhancing the warm wooden details of the walls and floor.
Loft in Portland

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

4.89 out of 5 average rating, 377 reviews
Top guest favourite
A cozy cottage is surrounded by lush trees and greenery. Two blue chairs are placed outside near the entrance, with a small table between them. A gas grill is positioned nearby, creating a welcoming space for outdoor relaxation and dining.
Cottage in Scarborough

Bright, clean, private cottage near Higgins Beach!

4.97 out of 5 average rating, 284 reviews
Top guest favourite
Flat in Portland

Safe, Quiet, Friendly area

4.91 out of 5 average rating, 285 reviews

When is the best time to visit Chebeague Island?

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Avg. price€211€211€191€211€217€259€310€328€266€239€231€245
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Destinations to explore