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Cottage vacation rentals in Westbrook

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Top-rated cottage rentals in Westbrook

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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.

5.0 out of 5 average rating, 107 reviews
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
Guest favorite
The exterior of the house is visible, featuring a light grey façade with multiple windows allowing natural light inside. A wooden deck is seen on the left, surrounded by trees. A patio area with stone accents is also present, offering potential for outdoor gatherings.
Cottage in Standish

Peaceful Lakeside Maine Retreat

Beautiful and peaceful lakeside retreat in Maine. With plenty of space for you and your family or friends to spread out and relax, this fully updated home has all of the features you'll need to enjoy your vacation on the water. Available for winter ice fishing, or get away from it all while working remotely using our reliable WiFi. Only half an hour from Portland's lighthouses and exceptional seafood and craft beer and two hours from Boston. Come and experience Maine - "the way life should be!"

4.92 out of 5 average rating, 139 reviews
Top guest favorite
An entryway features a red door, two clocks on the walls, and a small bar table with two stools. A mirror is mounted above the table, and the space is complemented by wood accents and light-colored flooring leading to the kitchenette.
Cottage in Portland

Cozy & Quiet Modern Cottage

Modern studio cottage designed and maintained with sustainability and eco-friendliness in mind, located in a quiet and very safe Portland neighborhood only a 7-10 minute drive (and $10-13 Uber/Lyft ride) from downtown Portland, the Old Port, and most local attractions. The cottage is a walkable mile (+/-) from Allagash Brewing (and the 4 other breweries there), and is within walking distance (.5 mi) of the restaurants and bars at Morrill's Corner. This is an LBGTQIA- and BIPOC-friendly space.

4.9 out of 5 average rating, 645 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.

4.99 out of 5 average rating, 483 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

Welcome to Maine. The way life should be! The Purple House (bc the paint color is a happy shade of light purple) is 2 floor home ACROSS the gravel road from Pettingill Pond. Less than 100 ft away from the dock with SHARED access with two super friendly neighbors in the Summer. As a guest of this house you have access to this pond where it is perfect for swimming, rowing, kayaking, canoeing, paddle boarding, boating, floating, ice skating, & snow shoeing. Quick 5 mins from the city center!

4.9 out of 5 average rating, 102 reviews
Superhost
A spacious bedroom features a minimalist wooden bed frame topped with a gray blanket. Two textured pillows in contrasting patterns rest against the headboard. On each side, modern wooden nightstands with soft lamps provide subtle illumination, enhancing the room's serene atmosphere.
Cottage in Portland

Cozy Urban Cottage on Munjoy Hill

Snack and sip your way through the food mecca that is Portland, Maine from this conveniently located, newly renovated 1860s vintage/modern cottage. The artfully appointed two bedroom home is easy walking distance from the Eastern Prom, the Old Port, and Bayside, the craft-brewing district, allowing guests a one-of-a-kind getaway. Original wood floors are paired with modern furniture, soft linens, and techy touches (Bluetooth speakers, Apple TV). Come for the lobster, stay for the lifestyle.

4.92 out of 5 average rating, 361 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.

4.97 out of 5 average rating, 306 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!

4.97 out of 5 average rating, 284 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.

4.81 out of 5 average rating, 120 reviews
Top guest favorite
Cottage in Buxton

Peaceful Cottage on Maine Flower Farm

Maine’s Peaceful Escape Nestled next door to Ferris Farm, our family-run flower farm, this charming cottage offers a private place to rest and recharge. Enjoy slow, coffee-filled mornings, quiet walks, and cozy evenings by the fire pit. Use the cottage as your home base to explore nearby beaches (30 minutes) or head into Portland (35 minutes) for breweries, coffee shops, and great dining. Perfect for a couple retreat, solo escape, or remote work getaway, with dedicated workspace.

4.97 out of 5 average rating, 188 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.

4.9 out of 5 average rating, 182 reviews

Popular amenities for Westbrook 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

4.95 out of 5 average rating, 180 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

4.93 out of 5 average rating, 213 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

4.94 out of 5 average rating, 50 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

4.92 out of 5 average rating, 79 reviews
Top guest favorite
Cottage in Wells

Paradise Found Minutes from Ogunquit | Heated Pool

5.0 out of 5 average rating, 94 reviews
Superhost
Cottage in Old Orchard Beach

Surf Inn #2

4.76 out of 5 average rating, 34 reviews
Superhost
A comfortable outdoor space is presented with a grassy area surrounded by trees. Blue chairs are arranged around a fire pit, and large windows of the two-story home reflect the natural light. A sense of privacy is offered by the surrounding foliage.
Cottage in Casco

Waterfront Getaway w/ Private Beach (HOT TUB)

4.8 out of 5 average rating, 45 reviews
Guest favorite
The cottage exterior features a welcoming entrance with a wooden porch and steps leading to a pink door. Large windows framed in white allow natural light to fill the space, surrounded by well-maintained landscaping with green grass and colorful flowers.
Cottage in Wells

Beautiful 2 bedrm cottage in Beach Dreams complex

4.94 out of 5 average rating, 48 reviews

Pet-friendly cottage rentals

Guest favorite
The exterior of the cottage features a shingled façade, an American flag displayed prominently. A window offers a glimpse of the interior, and a flower box filled with vibrant blooms enhances the welcoming entrance. The surrounding yard includes grassy areas and a stone pathway.
Cottage in Saco

Bright & Cozy Beachside Cottage in Camp Ellis

4.91 out of 5 average rating, 187 reviews
Guest favorite
The exterior of Pebble Cottage is shown, featuring a charming yellow facade with a welcoming front porch. Two large windows adorned with flower boxes are displayed, offering a glimpse of the landscaped yard framed by a white picket fence.
Cottage in Bridgton

Rustic Pebble Cottage in beautiful Bridgton, Maine

4.89 out of 5 average rating, 288 reviews
Guest favorite
The cottage entrance features a bright yellow door that adds a cheerful touch to the clean, white brick facade. The porch steps are flanked by landscaped greenery, leading to the front door. Gravel pathways and a textured mat provide access to the home.
Cottage in Falmouth

Osprey Cottage, peaceful setting, walk to beach

4.95 out of 5 average rating, 105 reviews
Top guest favorite
The cottage features a charming exterior with a wrap-around porch, complemented by wooden siding and decorative string lights. Tall trees provide shade around the property, creating a sense of tranquility. The house showcases multiple windows, allowing for natural light to brighten the interior.
Cottage in Bridgton

True Maine Artist Cottage with Outdoor Shower

4.91 out of 5 average rating, 225 reviews
Superhost
The exterior of a green craftsman-style home is shown, featuring a spacious yard surrounded by privacy hedges. Lush greenery and flower-filled bushes add to the landscape, with a deck visible at the back of the house. A bright sky peeks through scattered clouds.
Cottage in Falmouth

Historic Seaside Cottage 5 min from Portland!

4.73 out of 5 average rating, 240 reviews
Top guest favorite
A charming cottage exterior is displayed, featuring a bright white facade with green accents. Large windows and a welcoming front porch lead to a staircase. A garage is positioned adjacent to the house, and surrounding foliage adds a touch of nature to the scene.
Cottage in Falmouth

Sandy Seaside Cottage

4.93 out of 5 average rating, 30 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.

4.86 out of 5 average rating, 65 reviews
Top guest favorite
Cottage in Windham

Cozy Maine Lakefront Paradise

4.96 out of 5 average rating, 25 reviews

Private cottage rentals

Guest favorite
Cottage in Cape Elizabeth

Beach, Parks, Trails, Tranquil, Quiet, Peaceful

4.86 out of 5 average rating, 165 reviews
Guest favorite
An aerial view captures a serene point surrounded by calm water, with lush green trees lining the rocky shore. The rocky outcrop extends into the water, providing direct access to the tidal area. The tranquil setting highlights the natural beauty of the landscape.
Cottage in Harpswell

Rising Tide Times - quintessential Maine cottage

4.88 out of 5 average rating, 136 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

4.96 out of 5 average rating, 107 reviews
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

4.93 out of 5 average rating, 137 reviews
Guest favorite
Cottage in Yarmouth

Buoys on Bates | Couples' Cottage near Portland

4.95 out of 5 average rating, 182 reviews
Top guest favorite
A clean and functional kitchen features white cabinetry and a granite countertop. A refrigerator, dishwasher, and microwave are included, along with a stove. Natural light enters through a window above the sink, while a striped rug adds a touch of color to the wooden floor.
Cottage in Old Orchard Beach

Newly renovated beach cottage in Old OrchardBeach

4.95 out of 5 average rating, 132 reviews
Guest favorite
The exterior of the cottage is showcased, featuring gray siding and a prominent blue front door. Steps made of stone lead to the entrance, framed by small bushes and stones. Natural surroundings include trees in the background.
Cottage in Kennebunk

Quaint Year round Cottage

4.9 out of 5 average rating, 101 reviews
Top guest favorite
A serene lakeside scene is presented with two dark green Adirondack chairs positioned around a fire pit on a grassy area. A wooden dock extends into the lake, with a small boat resting beside it, surrounded by trees that frame the tranquil view.
Cottage in Raymond

Lovely Lakefront Cottage - Book Your Fall GetAway!

5.0 out of 5 average rating, 98 reviews

Destinations to explore