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Places to stay near Head Beach

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Top-rated vacation rentals near Head Beach

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The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.

Treehouse in Appleton

4.97 out of 5 average rating, 399 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Top guest favorite

The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.

Home in Georgetown

4.99 out of 5 average rating, 101 reviews

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Top guest favorite

A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.

Cottage in Brunswick

5 out of 5 average rating, 186 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

A cozy cabin is nestled within a forest, featuring a spacious covered porch and steps leading up to it. Seating is arranged around a fire pit in the foreground, with several black Adirondack chairs placed on a gravel surface, surrounded by lush greenery.

Cabin in Georgetown

4.87 out of 5 average rating, 131 reviews

Cozy log cabin on private pond, near Reid St Park!

Winter or summer, the Little River Retreat will help you step away from the world - but still be minutes from Reid State Park, Five Islands Lobster, the Georgetown General Store, and the rugged beauty of Midcoast Maine. This is our family camp, with our own books, games, and “vibe”. It is not a hotel, and some things may not be “industry standard”. We love the unique charm of this space and place, and many repeat guests do too. We hope you will treasure (and care for it) as we do!

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

4.98 out of 5 average rating, 431 reviews

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.

The two elevated structures of the tree dwelling are connected by a rope bridge, surrounded by lush green trees. Natural materials are utilized in the design, which includes a balcony and multiple levels that create a unique, inviting silhouette against the forest backdrop.

Treehouse in Georgetown

4.98 out of 5 average rating, 445 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

Top 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

4.98 out of 5 average rating, 319 reviews

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.

Top guest favorite

Cabin in Georgetown

4.99 out of 5 average rating, 161 reviews

Cedar Sauna+Near Beach/Hiking+Pond+FirePit

Come relax and unwind at Pine Cabin! * Cedar Barrel Sauna w/Glass Front * Minutes Reid State Park Beach & 5 Island🦞 * Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat & Automatic Kohler Generator * SmartTV & Record Player w/Vinyl *Pine Cabin is one of two cabins on our 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.

Two Adirondack chairs are positioned on a rocky area overlooking a serene waterfront. Trees frame the scene, with the sky displaying soft hues of pink and orange during sunset. The calm water reflects the natural beauty of the surroundings.

Home in Phippsburg

4.97 out of 5 average rating, 101 reviews

Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub

Experience authentic Midcoast Maine at this private and secluded waterfront home on Atkins Bay with unobstructed views of Popham Beach State Park’s unique flood plains, rocky coast, and 12-foot tides. The house is a recently renovated 3-bed, 2-bath with a large open living space, wrap-around screened porch, hot tub, and seating area overlooking Atkins Bay. Located two minutes driving from Popham Beach, Maine’s most beautiful beach!

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

4.93 out of 5 average rating, 276 reviews

Classic Maine, Modern Comfort

NOTE: Summer Bookings are 7 Days from Saturday-Saturday and tend to fill up by February/March or sooner. All the comforts of home while you're away from home. Come enjoy a newly built beach house (2008) just short walk from beautiful Popham Beach - one of Maine's most beautiful and expansive beaches, one hour north of Portland, Maine.

Top guest favorite

An open space features a vaulted wooden ceiling with beams and skylights. A cozy seating area includes a brown sofa and a modern coffee table. A wood stove adds warmth, while a well-equipped kitchen with dark green cabinets is visible in the background.

Tiny home in Freeport

4.99 out of 5 average rating, 320 reviews

Cozy Rock Cabin #thewaylifeshouldbe

*As seen on Magnolia Network's 'The Cabin Chronicles'* Cozy Rock Cabin is an 800 sq ft cabin on three acres of wooded land. Carefully designed for couples and digital nomads, it has everything you'll need to explore southern Maine (#thewaylifeshouldbe) or just stay cozy in front of a fire. Follow the journey on IG at @cozyrockcabin!

A view through large windows displays the serene Kennebec River and a private dock. Green trees lined along the opposite shore complement the scene. A blue glass bottle sits on the table in the foreground, adding a touch of color to the inviting atmosphere.

Home in Phippsburg

4.81 out of 5 average rating, 252 reviews

Lobstermans Way

Overlooking Fort Popham, the Kennebec River and entrance to Popham Beach State Park. The eagle population is back and there is a nest on the Bay. Private dock for relaxing or fishing! NO HIDDEN FEES As others have additional hidden fees above and beyond the nightly rate- for sheets -cleaning etc.this is the total nightly fee

Popular amenities for vacation rentals near Head Beach

Free parking on premises

Air conditioning

Other top sights near Head Beach

Coastal Maine Botanical Gardens296 locals recommend

Peaks Island257 locals recommend

Popham Beach State Park236 locals recommend

Pemaquid Point Lighthouse208 locals recommend

Crescent Beach State Park146 locals recommend

Wolfe's Neck Woods State Park178 locals recommend

Condo rentals with wifi

Top guest favorite

A modern living area is designed with large floor-to-ceiling windows that provide sweeping views of the marina and cityscape. A sleek black sectional sofa and matching ottoman are paired with a cozy armchair, accented by a striped red area rug on the hardwood floor.

Condo in Portland

4.97 out of 5 average rating, 221 reviews

Waterfront Two Master Suite Penthouse with Rooftop

Top guest favorite

A bright and airy living area is showcased with large glass doors letting in natural light. Potted plants are positioned throughout, and a sectional sofa offers comfortable seating. A media console holds a television, complemented by a small dining table and chairs in the background.

Condo in Old Orchard Beach

4.91 out of 5 average rating, 450 reviews

Luxury Beach Front Condo! Prime Location!

The entryway showcases a blend of modern and rustic elements, featuring a wooden accent wall and exposed brick. A low wooden bench and a round coffee table are positioned on a textured carpet, while a bank of mailboxes is mounted on one side, offering convenience for residents.

Condo in Portland

4.85 out of 5 average rating, 348 reviews

Old Port on foot

A warm wooden interior features a cozy seating area with a light-colored couch and decorative pillows. Floating shelves display various items, and the kitchen is visible in the background, showcasing essential appliances and a stylish design. Natural light filters through a skylight above.

Condo in Scarborough

4.96 out of 5 average rating, 385 reviews

Cozy condo by the beach!

A four-story oceanfront condo building features multiple balconies that overlook a sandy beach. Sunbathers and beach chairs are spread across the shoreline, with a vibrant atmosphere enhanced by people enjoying the coastal setting under a partly cloudy sky.

Condo in Old Orchard Beach

4.85 out of 5 average rating, 100 reviews

The Brunswick

Top guest favorite

A bright and airy kitchenette is shown, featuring white cabinetry and modern appliances. A comfortable blue sofa sits in the living area, with a dining space for four highlighted by pendant lights. Large windows allow natural light to fill the room, enhancing the inviting ambiance.

Condo in Portland

5 out of 5 average rating, 135 reviews

Mary J. Eastburn House--Baxter Suite

A cozy living area features wooden beams and paneling, with a comfortable sofa and an ottoman. Natural light enters through the windows, highlighting decorative shelves and a compact kitchen area. A small table and lamp add functionality to the space.

Condo in Scarborough

4.96 out of 5 average rating, 277 reviews

Comfy condo with loft by the beach!

The kitchen features modern stainless steel appliances, including a range and microwave. Granite countertops provide ample workspace, along with white cabinets for storage. A coffee maker and various utensils are neatly arranged, contributing to a functional and well-equipped cooking area.

Condo in Portland

4.87 out of 5 average rating, 442 reviews

Renovated Exchange St. Loft w/Free Parking

Family-friendly house rentals

Top guest favorite

A charming waterfront cottage is presented with a bright blue door and two red chairs on a stone patio. Lush greenery surrounds the property, enhancing its inviting exterior. The tranquil waters of Pettingill Pond can be seen in the background, reflecting the sky.

Home in Windham

4.95 out of 5 average rating, 167 reviews

Waterfront Gem walkable to Restaurants!

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

4.93 out of 5 average rating, 135 reviews

Stone Isle. 8 acres next 2 little john preserve.

A lofted bedroom features a spacious bed adorned with a vibrant striped blanket. Light filters through a window, highlighting the sloped whitewashed ceilings and simple artwork on the walls. Warm wood accents complement the soft, neutral tones throughout the room.

Home in Bridgton

4.98 out of 5 average rating, 138 reviews

Wren Cabin + Wood fired Sauna

Top guest favorite

A charming white cottage with a sloped roof is situated near the water's edge. Orange window boxes add a pop of color to the exterior, while a stone patio features several wooden chairs. Lush greenery surrounds the property, providing a natural backdrop.

4.91 out of 5 average rating, 362 reviews

Gorgeous Studio on the Kennebec

Top guest favorite

A sleeping area features a light blue headboard paired with a patterned quilt and striped pillows on a spacious bed. A lamp sits on a bedside table next to the bed. Soft light enters through the partially open window, enhancing the calming ambiance.

4.93 out of 5 average rating, 455 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Top guest favorite

A charming cottage with wooden siding is surrounded by landscaped gardens and large rocks. The covered porch features rocking chairs, inviting relaxation. Windows allow for natural light, and tall trees frame the property, contributing to a serene outdoor setting.

Home in Edgecomb

4.94 out of 5 average rating, 493 reviews

Sheepscot Harbour Cottage/waterview

Top guest favorite

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

4.98 out of 5 average rating, 218 reviews

Waterfront Cottage On Basin Cove - Amazing Sunsets

Top guest favorite

The rocky coast is lined with spruce trees, showcasing natural contours along the shoreline. Calm blue waters gently lap against the rocks, while a clear sky enhances the scenic view. A few homes are nestled among the trees, blending harmoniously with the coastal landscape.

Home in Georgetown

5 out of 5 average rating, 116 reviews

Perched atop the Coast of the Atlantic Ocean

Apartment rentals with air conditioning

Top guest favorite

An open dining area features a round wooden table surrounded by blue chairs. A comfortable living room area is visible, with a gray sofa and art on the walls. Large windows allow natural light to brighten the space, enhancing the modern design.

Apartment in Portland

4.98 out of 5 average rating, 112 reviews

Harborview - Curated East End Escape w/ Parking

A bright hallway features wooden flooring and natural light filtering through large windows. Exposed wooden beams and a brick wall add character. A cozy seating area with red sofas is visible at the end, alongside a modern kitchen space. A bathroom door is located to the left.

Apartment in Portland

4.94 out of 5 average rating, 705 reviews

Extraordinary Architectural Masterpiece Downtown

Top guest favorite

An inviting entrance features a white door with glass panes, framed by red trim. A decorative wheel hangs on the wall, while a flowering planter adds a touch of greenery. Sunlight casts soft shadows on the rustic shingled exterior.

Apartment in Boothbay

4.97 out of 5 average rating, 351 reviews

Sunnymeade

Top guest favorite

The airy living area features a neutral-toned sofa, complemented by two stylish chairs and a round glass coffee table. Soft light enters through two windows, and a vibrant abstract painting is displayed on the wall. Decorative lamps add subtle illumination.

Apartment in Cape Elizabeth

4.99 out of 5 average rating, 281 reviews

Cape Elizabeth Garden Apt+Beach+Close to Portland!

Two vintage-style homes are set against a backdrop of tall trees under a clear blue sky. One home is slightly elevated, showcasing a classic white exterior with dark shutters, while the other features a wraparound porch and larger windows, blending harmoniously with the natural landscape.

Apartment in Freeport

4.92 out of 5 average rating, 243 reviews

1000 sq. ft. 1BR+ Apt Close to Town & Nature

Top guest favorite

A spacious two-story home is shown with a welcoming front porch adorned with rocking chairs. Solar panels are visible on the roof, which is complemented by several skylights. Surrounding greenery enhances the peaceful setting under a partly cloudy sky.

Apartment in Harpswell

4.93 out of 5 average rating, 214 reviews

Comfortable studio apartment in quiet location

Top guest favorite

A welcoming living space features two comfortable armchairs and a soft couch, with a wooden coffee table at the center. Large windows provide abundant natural light and views of the water. A well-equipped kitchen is visible in the background, along with light-colored cabinetry.

Apartment in Boothbay Harbor

5 out of 5 average rating, 129 reviews

Sail Loft - Upscale Oceanfront on a Pier near BBH!

An inviting living area showcases a modern spiral staircase leading to the loft. A sleek kitchen is visible, featuring patterned backsplash tiles and stainless-steel appliances. A comfortable sofa and a coffee table create a cozy seating arrangement, complemented by natural light from the large windows.

Apartment in Brunswick

4.91 out of 5 average rating, 675 reviews

Downtown Hideaway-Loft HotTub Modern Clean Private

Other great vacation rentals near Head Beach

The exterior of the multi-unit house is shown, featuring a light gray facade and a red roof. An expansive wooden deck is visible on the second level, overlooking the green lawn. Bright flowers adorn the entrance, adding a touch of color to the outdoor space.

Apartment in Orr's Island

4.94 out of 5 average rating, 104 reviews

Shore House, Leona Unit - Ocean Front Property

Top guest favorite

An aerial view captures a secluded log cabin surrounded by lush greenery on a private island. A wooden dock extends over the tranquil water, providing access to the cabin, which is nestled among trees. Sunlight glistens on the lake's surface.

Island in Monmouth

4.98 out of 5 average rating, 255 reviews

Naughty Dog Private Island Log Cabin

Top guest favorite

A scenic view is captured from the deck, showcasing the tranquil waters of Jones Cove with lush greenery lining the shore. In the distance, small islands are visible under a clear blue sky, creating an inviting atmosphere for relaxation.

Guesthouse in South Bristol

4.98 out of 5 average rating, 420 reviews

Waterfront Guest House on the Maine Coast

Top guest favorite

A bright bedroom features a large bed made with subtle striped bedding. Natural light filters through three windows, illuminating the light wood floor. A hammock chair hangs from the ceiling, and a potted plant is placed by the wall, adding a touch of greenery.

Guest suite in Phippsburg

5 out of 5 average rating, 132 reviews

Suite 19 min to Popham, 10 min to Bath

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

4.9 out of 5 average rating, 164 reviews

Classic Maine Cottage - dock, sauna & kayaks

Top guest favorite

The modern retreat is nestled among trees, featuring a deck with outdoor seating and a picnic table. The structure showcases large windows, allowing natural light to fill the interior, with a welcoming red door standing out against the dark exterior.

Guesthouse in Newcastle

4.98 out of 5 average rating, 119 reviews

Modern 1-BR I Wooded Retreat I Mid-Coast Maine

The cabin is illuminated warmly at dusk, featuring a hot tub in the backyard. Outdoor seating arrangements with four chairs are positioned around a fire pit, set against a backdrop of trees, creating a serene and inviting atmosphere.

Cabin in Kennebunk

4.98 out of 5 average rating, 169 reviews

HotTub/5min to K-port, Pet friendly, @anchorunwind

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

4.99 out of 5 average rating, 423 reviews

Dreamy Post&Beam Hideaway Near Portland & Freeport