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Cottage vacation rentals in Small Point

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Top-rated cottage rentals in Small Point

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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.

4.87 out of 5 average rating, 239 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.

5.0 out of 5 average rating, 105 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.

4.96 out of 5 average rating, 179 reviews
Top guest favorite
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.

4.93 out of 5 average rating, 302 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, 479 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, 301 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.

4.82 out of 5 average rating, 119 reviews
Top guest favorite
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.

4.93 out of 5 average rating, 135 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.

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.

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.

4.97 out of 5 average rating, 381 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

Classic Maine cottage on the end of a point, surrounded by water on 3 sides provides stunning views. The perfect backdrop for the quintessential cottage vacation. Features spacious decks, direct tidal access for kayaking, and outdoor firepit. 15 min to downtown Brunswick/45 min to Portland. We even have Kayaks onsite for guests to paddle around Cards Cove. Perfect for couples and families!

4.89 out of 5 average rating, 133 reviews

Popular amenities for Small Point 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, 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

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

Stillhouse: Serene sanctuary in coastal Maine

5.0 out of 5 average rating, 7 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, 76 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

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

4.94 out of 5 average rating, 47 reviews
Top guest favorite
Cottage in Wells

Paradise Found Minutes from Ogunquit | Heated Pool

5.0 out of 5 average rating, 88 reviews
Superhost
Cottage in Old Orchard Beach

Surf Inn #2

4.79 out of 5 average rating, 33 reviews

Pet-friendly cottage rentals

Guest favorite
A wooden cottage is featured, with natural wood siding and expansive windows. A wraparound deck provides outdoor space for relaxation, surrounded by a lush green landscape of trees and foliage. Pathway stones lead to the entrance, enhancing the welcoming appearance.
Cottage in South Bristol

Cottage on an island on the end of a peninsula W

4.93 out of 5 average rating, 117 reviews
Top guest favorite
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

4.92 out of 5 average rating, 335 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

4.95 out of 5 average rating, 117 reviews
Top guest favorite
The exterior of the cottage features a welcoming wooden deck with seating underneath a blue umbrella, surrounded by green grass and blooming flowers. A fire pit and two Adirondack chairs are positioned on the lawn, providing a cozy outdoor gathering space.
Cottage in Boothbay

Cottage in the woods on Ocean Point

5.0 out of 5 average rating, 136 reviews
Guest favorite
The serene view showcases a sunrise over the calm waters of the Sasanoa River, reflecting golden hues. Lush greenery frames the scene, while the distant treeline adds depth to the landscape. Soft clouds linger above, enhancing the tranquil atmosphere of the setting.
Cottage in Woolwich

Pet Friendly Audubon Bring Your Fishing Gear!

4.91 out of 5 average rating, 224 reviews
Top guest favorite
A charming cottage is nestled among tall trees, featuring a welcoming entrance with wooden doors. A small porch is adorned with a chair, providing a peaceful spot to enjoy the surrounding woodland. Multiple windows enhance the cabin's light-filled exterior.
Cottage in Wiscasset

Waterscape Cottage - private waterfront

4.89 out of 5 average rating, 325 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

4.95 out of 5 average rating, 526 reviews
Guest favorite
A charming cottage is nestled among trees, showcasing a tranquil setting. Two Adirondack chairs are positioned on the grass, inviting relaxation while offering a view of the water in the distance. A well-maintained garden features vibrant greenery and blooming white flowers.
Cottage in Edgecomb

Spectacular Water View Cottage

4.92 out of 5 average rating, 180 reviews

Private cottage rentals

Guest favorite
The cottage features a single-story facade with grey siding and a well-maintained garden area. A gravel path leads to the entrance, flanked by outdoor seating that includes a round table and chairs. American flags are displayed, and the Sheepscot River is visible in the background.
Cottage in Edgecomb

Waterfront Getaway & Scenic View

4.96 out of 5 average rating, 99 reviews
Top guest favorite
The cottage features a traditional design with natural wood siding and a spacious screened-in porch, offering views of the surrounding landscape. Tall trees frame the home, and uneven rocky terrain leads to the base of the structure, enhancing the natural setting.
Cottage in Edgecomb

Coastal Cotton Cottage on Sheepscot Harbour

4.98 out of 5 average rating, 115 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

4.99 out of 5 average rating, 89 reviews
Superhost
A charming two-story cottage is surrounded by lush greenery. The exterior features white siding with red-trimmed windows. A welcoming porch with railings is visible at the front, providing access to the entrance. A smaller structure is seen in the background, partially obscured by the trees.
Cottage in Phippsburg

Sweet comfy cottage on Small Point Road

4.57 out of 5 average rating, 141 reviews
Guest favorite
A newly renovated cottage is situated on a spacious grassy lot, surrounded by trees. A picnic table and several outdoor chairs are positioned in the foreground, while a walkway leads to the front steps. Large windows provide ample natural light, enhancing the inviting exterior.
Cottage in Phippsburg

Drift Away Cottage on Popham Beach

4.95 out of 5 average rating, 78 reviews
Superhost
A cottage exterior is shown, featuring large windows that allow natural light into the interior. Two white adirondack chairs are positioned on the porch, and a stone chimney rises from the roof, blending rustic charm with coastal aesthetics.
Cottage in Phippsburg

Beachfront Driftwood Cottage

4.81 out of 5 average rating, 36 reviews
Top guest favorite
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!

5.0 out of 5 average rating, 25 reviews
Top guest favorite
A quaint cottage is surrounded by a vintage garden featuring a variety of colorful flowers and foliage. A screened-in porch is visible, adorned with hanging plants. Benches offer seating among lush greenery, while flower boxes add character to the tranquil outdoor setting.
Cottage in Bristol

Coast of Maine Cottage: Blue Moon Cottage

4.94 out of 5 average rating, 19 reviews

Destinations to explore