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Cottage holiday rentals in Bailey Island

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Top-rated cottage rentals in Bailey Island

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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.

FamilyLocationIndoor spaces

4.87 out of 5 average rating, 239 reviews
Top Guest favourite
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.

FamilyValueLaundry

4.96 out of 5 average rating, 179 reviews
Top Guest favourite
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.

FamilyLocationWalkability

5.0 out of 5 average rating, 104 reviews
Top Guest favourite
A serene waterfront scene captures the sun setting over a calm bay, with reflections in the water. In the foreground, tall grasses and wildflowers frame the image, leading to a dock with two Adirondack chairs arranged for relaxation.
Cottage in Topsham

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

FamilyValueOutdoor spaces

4.93 out of 5 average rating, 302 reviews
Top Guest favourite
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.

LocationValueSleep quality

4.99 out of 5 average rating, 477 reviews
Top Guest favourite
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.

ValueFamilyCheck-in

4.97 out of 5 average rating, 301 reviews
Guest favourite
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.

FamilyLocationShared spaces

4.82 out of 5 average rating, 119 reviews
Top Guest favourite
The image captures a serene riverside scene along the New Meadows River during sunset. Calm waters reflect the clear blue sky, while trees line the banks. Nearby, natural elements like rocky shores and patches of snow create a peaceful outdoor setting.
Cottage in West Bath

Coastal Waterfront Cottage in West Bath

***Please Message me to ask about possible discounts and length of stay minimums.*** 4 season home right on the waters edge on New Meadows River in West Bath sits this newly remodeled home. Fully furnished and includes a Minisplit Heat Pump/ AC, and Propane fireplace. Great location as it is on a dead end road that is just minutes to shopping, restaurants, etc. Incredible spot to watch the boats come and go as Sawyer park boat launch as well as the town boat launch are right in view.

ValueLocationSleep quality

4.93 out of 5 average rating, 134 reviews
Top Guest favourite
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.

LocationFamilyDecor

4.98 out of 5 average rating, 496 reviews
Guest favourite
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.

FamilyLocationGetting around

4.89 out of 5 average rating, 180 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

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.

ValueFamilyHospitality

4.97 out of 5 average rating, 381 reviews
Top Guest favourite
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.

ValueLocationDecor

4.96 out of 5 average rating, 212 reviews

Popular amenities for Bailey Island cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top Guest favourite
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

LocationFamilyPool

4.95 out of 5 average rating, 179 reviews
Guest favourite
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

LocationValueHospitality

4.93 out of 5 average rating, 213 reviews
Guest favourite
Cottage in Harpswell

Stillhouse: Serene sanctuary in coastal Maine

LocationQuietHot tub

5.0 out of 5 average rating, 7 reviews
Guest favourite
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

LocationValueSleep quality

4.92 out of 5 average rating, 76 reviews
Guest favourite
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

LocationFamilyOutdoor spaces

4.86 out of 5 average rating, 29 reviews
Top Guest favourite
A charming cottage is nestled among vibrant autumn foliage. The exterior features a covered porch with two red chairs, a picnic table on a grassy lawn, and a nearby outdoor grill. Large windows accentuate the welcoming facade of the home.
Cottage in Camden

Megunticook Retreat

LocationIndoor spacesCleanliness

5.0 out of 5 average rating, 57 reviews
Guest favourite
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

FamilyValueCondition

4.94 out of 5 average rating, 47 reviews
Top Guest favourite
Cottage in Wells

Paradise Found Minutes from Ogunquit | Heated Pool

ValueLocationComfort

5.0 out of 5 average rating, 88 reviews

Pet-friendly cottage rentals

Guest favourite
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

ValueFamilySleep quality

4.97 out of 5 average rating, 104 reviews
Guest favourite
An outdoor area features a wooden deck with a railing overlooking the ocean. Two round tables are positioned beside four wicker chairs, providing a comfortable space for relaxation. The calm water and distant shoreline are visible in the background under a clear sky.
Cottage in Saco

Ocean Views/Huge Porch/Sleeps 12/Walk to Beach

FamilyValueIndoor spaces

4.85 out of 5 average rating, 123 reviews
Top Guest favourite
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

LocationFamilyAccess

4.99 out of 5 average rating, 184 reviews
Guest favourite
Cottage in Lincolnville

Call of the Loon - Water Edge Lake House

ValueLocationIndoor spaces

4.83 out of 5 average rating, 115 reviews
Top Guest favourite
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

LocationFamilyOutdoor spaces

4.95 out of 5 average rating, 116 reviews
Top Guest favourite
A serene ocean view showcases a sailboat gliding across calm waters, framed by lush greenery and a rocky coastline. The expansive sky is filled with soft clouds, creating a tranquil atmosphere that invites relaxation and reflection.
Cottage in South Thomaston

Cottage by the sea private oceanfront shoreline

FamilyLocationLayout

4.94 out of 5 average rating, 149 reviews
Top Guest favourite
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

ValueLocationCleanliness

4.95 out of 5 average rating, 526 reviews
Top Guest favourite
A circular tree swing hangs from a sturdy branch, overlooking a spacious green yard. The view includes a serene body of water with a dock and distant islands framed by trees under a clear blue sky.
Cottage in Friendship

Our charming,oceanfront, Bradford point cottage

LocationValueParks

4.92 out of 5 average rating, 335 reviews

Private cottage rentals

Guest favourite
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

FamilyLocationCleanliness

4.96 out of 5 average rating, 106 reviews
Superhost
Cottage in Harpswell

Cottage located near the giant stairs.

LocationFamilyComfort

4.78 out of 5 average rating, 23 reviews
Guest favourite
A serene waterfront view showcases a vibrant sunset reflected on calm waters. Silhouetted trees frame the scene, highlighting the tranquil atmosphere created by the array of warm colors in the sky and the peaceful surrounding landscape.
Cottage in Harpswell

Basin Cove Retreat: Perfect to explore Mid-Coast

FamilyLocationKitchen

4.87 out of 5 average rating, 85 reviews
Top Guest favourite
A two-story cottage is set against a backdrop of lush trees. The house features multiple windows, framed in white, reflecting the natural light. A deck extends toward the water, inviting views of the surrounding landscape. A rocky shoreline complements the scene.
Cottage in Harpswell

Seaside-The way life should be!

FamilyLocationView

5.0 out of 5 average rating, 25 reviews
Top Guest favourite
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

LocationHikingView

5.0 out of 5 average rating, 13 reviews
Top Guest favourite
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

LocationFamilyHospitality

4.99 out of 5 average rating, 89 reviews
Top Guest favourite
The exterior of a cottage with a white facade and green trim is showcased. A wooden staircase leads to a screened porch with a door displaying the number 9. An American flag is visible in the background, complementing the natural surroundings.
Cottage in Harpswell

Old fashion neighborhood near the water.

FamilyLocationHeating

4.95 out of 5 average rating, 66 reviews
Guest favourite
The living room features two comfortable sofas arranged around a central coffee table. Large windows provide views of the water, while a TV is mounted on a wall. Soft lighting and natural wood beams enhance the inviting space.
Cottage in Harpswell

Oceanfront Serenity – Stargaze & Unwind-

ValueFamilySleep quality

4.95 out of 5 average rating, 41 reviews

Destinations to explore