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Cottage vacation rentals in Chebeague Island

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Quick stats about cottage rentals in Chebeague Island

  • Total vacation rentals

    Explore 50 vacation rentals in Chebeague Island

  • Nightly prices starting at

    Chebeague Island vacation rentals start at ﺩ.ﺇ 624 per night before taxes and fees

  • Verified guest reviews

    Over 1,300 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Chebeague Island vacation 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 cottage rentals in Chebeague Island

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

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Guest favorite
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.

ValueLocationAmenities

4.87 out of 5 average rating, 239 reviews
Top guest favorite
Cottage in Yarmouth

Buoys on Bates | Couples' Cottage near Portland

Buoys on Bates is a newly renovated, contemporary cottage 15 minutes from Portland and moments from Yarmouth's historic Main Street. Step into a spotless, light filled space with a full kitchen, fast 350 Mbps wifi, premium Tuft & Needle queen bed, in-unit washer/dryer, efficient A/C, and Level 2 EV charger right at the door. Walk to shops, restaurants, and the Royal River, then set out for Portland, Freeport, beaches, and breweries. Buoys on Bates is your easy, comfortable base for all of Maine.

LocationFamilyKitchen

4.96 out of 5 average rating, 179 reviews
Top guest favorite
An inviting entryway is presented under a large, sloping roof supported by exposed wooden beams. Comfortable seating is arranged on the porch, with decorative pumpkins placed on the ground. Pathways made of stones lead to the entrance, surrounded by a tranquil natural setting.
Cottage in Biddeford

Secluded Coastal Home & Cottage 3 Minutes to Beach

Escape to Thistle Pond Cottage, a peaceful coastal retreat in southern Maine. Nestled on 2 acres with pond views, lush gardens, and local wildlife, it’s minutes from beaches and Portland. Every stay begins with homemade bread from our kitchen and thoughtful, locally sourced welcome accompaniments. Weather and seasonal permitting, guests may occasionally savor a host-prepared wood-fired pizza made with fresh garden ingredients. Cozy, bright, and full of garden-to-table charm and seasonal delight.

FamilyValueGrill

5.0 out of 5 average rating, 105 reviews
Top guest favorite
The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.
Cottage in Pownal

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

ValueFamilyView

4.99 out of 5 average rating, 477 reviews
Top guest favorite
Cottage in Portland

4br2ba House+parking@PeacefulOasis on Munjoy Hill

This standalone 1500sf 3-story cottage is set in an ideal location, close to the Eastern Prom, cafes, award-winning restaurants, breweries and the Old Port. -Main floor: well-equipped kitchen + open concept living/dining room -Upper floor: 3BR (1 queen, 1 full, 1 twin) + bath -Garden level: 1BR/1 bath (queen) with private entrance - Off-street parking for 1 car This charming home @ A Peaceful Oasis offers plenty of space, privacy & comfort, making it the perfect home base for your stay.

FamilyValueCheck-in

4.97 out of 5 average rating, 301 reviews
Top guest favorite
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!

Nestled amongst the trees and located just 2 miles from beautiful Higgins Beach and just 5 miles to Portland, this recently renovated, sparkling clean, bright, private, stunning cottage is waiting just for you! Your private entrance is just steps away from your parked car. The cottage is 16 x 20 so it's super cozy! We live on the property (so we're here if you need us) but you are 100 feet from us, way out in the backyard. (It's private!) Our location is perfect for your Maine vacation!

FamilyValueOutdoor spaces

4.97 out of 5 average rating, 274 reviews
Guest favorite
A scenic view of a tranquil lake is captured, with a boat dock extending into the water. A boat is anchored near the dock, surrounded by lush greenery. A picnic table sits on sandy ground nearby, inviting relaxation by the lakeside.
Cottage in Gray

Edgewater Retreat - Lakefront w/Sauna & EV Charger

Welcome to Edgewater Retreat! This custom-built cottage features lakefront views and access to three beaches: secluded pocket beach in front of cottage, boaters beach with docks, and a full sun sandy bottom swim beach. Enjoy an unforgettable Maine vacation. Paddlecraft on the water, lounge in the hammocks, S'mores by the campfire, canoe to nearby island for offshore yoga, and gril with friends & family. In winter, enjoy ice fishing and kids enjoy snow sledding on adjacent hill.

ValueLocationAccess

4.82 out of 5 average rating, 119 reviews
Guest favorite
A cozy cottage exterior is depicted, featuring white siding and a green roof. A screened-in porch with comfortable seating is prominently displayed, along with a wooden entrance staircase. The surrounding area includes natural vegetation and a pathway made from red bricks, providing a welcoming access point.
Cottage in Standish

The Loon's Nest Cottage

Located only 30 minutes from Portland this adorable and cozy cottage sits 10 feet from Watchic Lake. Listen to the loons all day, paddle to an island, stare at the glassy lake from the breakfast nook, swim forever, read a book in the screened-in porch or toast marshmallows in the firepit, whichever it may be you'll simply enjoy the peace and tranquility of this very private Maine lake house nestled in the woods. If you’re feeling like a hike, a dinner out there are options a plenty!

FamilyLocationDecor

4.96 out of 5 average rating, 106 reviews
Top guest favorite
The cozy cottage exterior is illuminated in the evening, highlighted by a bright red front door. Soft light glows from the windows, surrounded by lush greenery. A path with wet pavement reflects the light, creating a welcoming entrance amidst the serene wooded surroundings.
Cottage in Boothbay Harbor

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

LocationFamilyNearby

4.98 out of 5 average rating, 496 reviews
Guest favorite
A tranquil view of the ocean is visible from a spacious wooden deck, featuring several white Adirondack chairs. The calm water reflects the clear blue sky and surrounding greenery, while distant islands can be seen along the horizon.
Cottage in Harpswell

Classic Maine Cottage - dock, sauna & kayaks

The Perfect Maine Cottage! On the edge of the ocean, carefully preserved with traditional details. Charming, open floor plan, with a wall of windows to the ocean. Sunny large wrap-around deck and screen porch creates beautiful outside spaces to enjoy. Perfect for listening to waves and watch lobstermen pull up their traps. Cathedral ceilings and Scandinavian design gives the cottage an exclusive feeling. Gentle stairs lead to the private deep water dock for all kinds of boating.

FamilyValueGrill

4.89 out of 5 average rating, 180 reviews
Guest favorite
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

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.

ValueLocationAmenities

4.97 out of 5 average rating, 381 reviews
Top guest favorite
An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.
Cottage in South Thomaston

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

LocationValueWifi

4.96 out of 5 average rating, 212 reviews

Popular amenities for Chebeague Island cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top guest favorite
A bright kitchen area features modern white cabinetry and a spacious countertop. Barstools with woven seats are positioned at the counter. Natural light floods in through a nearby door, illuminating the polished wooden floor and light blue walls.
Cottage in Wells

Cozy Cottage with Ocean Views, Wells Maine

ValueLocationBeach

4.95 out of 5 average rating, 179 reviews
Guest favorite
A grassy area features seating made up of Adirondack chairs and a patio table set, facing a row of cottages with large windows. The clear sky above is dotted with clouds, complementing the peaceful surroundings.
Cottage in Wells

Wells Maine Home with a View

LocationValueIndoor spaces

4.93 out of 5 average rating, 213 reviews
Guest favorite
A bright living area features a comfortable gray sofa adorned with patterned cushions, complemented by a cozy teal accent chair. A round wooden coffee table sits in front, surrounded by a light area rug. Bookshelves and decorative elements enhance the inviting ambiance.
Cottage in Kennebunk

Fully Renovated/4min to K-port/HotTub/Game Room

ValueLocationQuiet

4.92 out of 5 average rating, 76 reviews
Guest favorite
Cottage in Harpswell

Stillhouse: Serene sanctuary in coastal Maine

LocationEV chargingView

5.0 out of 5 average rating, 7 reviews
Guest favorite
An outdoor fire pit is surrounded by several Adirondack chairs, positioned on a sandy area. Trees frame the scene, with a serene view of the water and a colorful sunset in the background.
Cottage in Cushing

Oceanfront Family Getaway - 8BR/6BA/5Acres

ValueLocationGetting around

4.86 out of 5 average rating, 29 reviews
Guest favorite
The exterior of a private guest cottage is illuminated at dusk, surrounded by trees. A well-maintained courtyard includes decorative lighting, stone pathways, and gravel. The cottage features a charming facade with a rooftop dormer and windows that invite natural light.
Cottage in Portland

Lovely 2-Story Cottage w/ Hot Tub & AC by Downtown

ValueFamilyKitchen

4.94 out of 5 average rating, 47 reviews
Superhost
Cottage in Old Orchard Beach

Surf Inn #2

LocationValueNearby

4.79 out of 5 average rating, 33 reviews
Top guest favorite
Cottage in Wells

Paradise Found Minutes from Ogunquit | Heated Pool

FamilyValueCheckout

5.0 out of 5 average rating, 88 reviews

Pet-friendly cottage rentals

Guest favorite
A fire pit area features a circular arrangement of brightly colored chairs on a well-maintained lawn. The ocean view is visible in the background, framed by trees. Gentle waves can be seen at a distance, enhancing the tranquil outdoor space.
Cottage in New Harbor

Captains View at Pemaquid Point

LocationValueTV

4.97 out of 5 average rating, 104 reviews
Top guest favorite
A spacious living area features a large sectional sofa adorned with decorative pillows. A mural of mountains and a lake provides a scenic backdrop. Natural light fills the room through a large window with sheer curtains, complemented by light wooden flooring and a textured area rug.
Cottage in Wakefield

Lake View Cottage / Fenced in Yard / Pet Friendly

LocationFamilyIndoor spaces

4.93 out of 5 average rating, 225 reviews
Top guest favorite
A modern two-story home is set amidst a wooded area, featuring a spacious outdoor seating arrangement with a picnic table and various chairs. A fire pit and grill are present, with the soft glow of twilight highlighting the inviting exterior.
Cottage in Acton

Eclectic Lakefront Cottage on Great East Lake

LocationValueAir conditioning

4.99 out of 5 average rating, 184 reviews
Top guest favorite
A charming cottage is presented with a spacious front porch featuring multiple windows and a balcony above. The exterior showcases a combination of textured siding and stone accents, flanked by a neatly landscaped yard with a rock border.
Cottage in Edgecomb

Sheepscot Harbour Village - 3 Bd Condo Waterview

FamilyLocationAmenities

4.95 out of 5 average rating, 117 reviews
Top guest favorite
A bright living space features a comfortable dark sofa facing a small wooden coffee table. A round dining table with two chairs is visible in the background. Large windows allow natural light to fill the room, complemented by pale curtains and wooden flooring.
Cottage in Windham

The Purple House by Pettingill Pond

FamilyLocationNearby

4.9 out of 5 average rating, 101 reviews
Guest favorite
Cottage in Lyman

Cozy Waterfront Cottage w/ Private Dock & Kayaks

LocationValueHiking

4.83 out of 5 average rating, 120 reviews
Top guest favorite
A beverage sits on a small table beside a glass bottle filled with sticks. The view through a window reveals the sandy beach and calming ocean waves, with a colorful sunset casting soft hues in the sky. An American flag is partially visible in the background.
Cottage in Saco

Deja Blue Guesthouse

FamilyValueHospitality

4.95 out of 5 average rating, 526 reviews
Top guest favorite
The open-concept living area features a modern kitchen with a breakfast bar and a wooden countertop. A cozy seating area includes a sofa with decorative pillows, a wooden coffee table, and soft lighting from lamps, creating a relaxed environment with warm tones.
Cottage in Old Orchard Beach

#4 Vintage Cottage walk to the beach and Pier!

FamilyLocationAccuracy

4.94 out of 5 average rating, 342 reviews

Private cottage rentals

Top guest favorite
A serene lake view is depicted, showcasing calm waters reflecting the sky and surrounding trees. A private dock is visible at the water’s edge, adding to the tranquil atmosphere. The natural landscape features a variety of green hues from the trees lining the shore.
Cottage in Raymond

Relax by a Quiet Lake

FamilyValueGetting around

4.93 out of 5 average rating, 135 reviews
Superhost
A charming cottage is presented with a spacious deck and large windows, allowing for ample natural light. Surrounded by lush greenery, the home features a combination of wooden shingles and blue accents, emphasizing its coastal setting. The deck is accessible, providing views of the landscape.
Cottage in Long Island

Grace Cottage

LocationValueBeach

4.92 out of 5 average rating, 49 reviews
Top guest favorite
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

LocationFamilyKitchen

4.99 out of 5 average rating, 89 reviews
Superhost
A charming red cottage is nestled among greenery, featuring a wrap-around porch with multiple entry points. The house, with a sloped roof and white trim, is set against a backdrop of tall trees and a grassy lawn, creating a serene outdoor setting.
Cottage in Long Island

Maine island vacation cottage

FamilyValueAmenities

4.61 out of 5 average rating, 61 reviews
Guest favorite
A charming cottage exterior is highlighted by vibrant flowerbeds featuring yellow, pink, and blue blooms. A large deck is visible, complemented by a patio umbrella. The home's red facade and white railings create a welcoming atmosphere, surrounded by lush greenery.
Cottage in Long Island

Picturesque Maine water view Long Island

FamilyValueComfort

4.82 out of 5 average rating, 51 reviews
Guest favorite
A cozy living area offers a light-filled space with a comfortable sofa and armchair. A wooden coffee table is positioned in front of the seating. The adjacent dining area features a wooden table with two chairs, welcoming natural light from multiple windows.
Cottage in Higgins Beach

2 Bedroom Cottage - Walk to the beach in 2 minutes

LocationFamilyGrill

4.94 out of 5 average rating, 36 reviews
Guest favorite
A wooden dock extends over calm waters, leading toward a flagpole displaying the American flag. Lush greenery lines the shore in the background, creating a serene coastal atmosphere. The dock features railings along the sides, providing unobstructed views of the surrounding natural landscape.
Cottage in Yarmouth

Demure coastal cottage steps to private beach.

FamilyLocationIndoor spaces

4.85 out of 5 average rating, 62 reviews
Top guest favorite
A view of the serene ocean can be seen through the trees from the backyard of the cottage. The clear blue sky reflects upon the water's surface, offering an inviting atmosphere. The well-maintained grass extends toward the water, creating a peaceful outdoor space.
Cottage in Harpswell

Newly renovated cottage with stunning ocean views

LocationAccessCondition

5.0 out of 5 average rating, 13 reviews

Destinations to explore