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Places to stay near Portland Head Light

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Top-rated holiday rentals near Portland Head Light

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

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Top guest favourite
A modern cabin with an A-frame shape is illuminated by warm lights, surrounded by tall trees. In front, a fire pit with wooden chairs invites gatherings, while a hot tub and sauna are visible nearby, contributing to the outdoor relaxation space.
Cabin in South Berwick
5 out of 5 average rating, 304 reviews

Romantic A-Frame cabin in the woods

Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

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
4.99 out of 5 average rating, 458 reviews

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.

Top guest favourite
An aerial view captures a serene coastal neighborhood with waterfront homes and manicured lawns. The ocean sparkles in the distance, and several boats can be seen on the water. A well-maintained driveway leads to a residence surrounded by lush greenery.
Guest suite in South Portland
4.97 out of 5 average rating, 105 reviews

Ocean Views, work friendly

This space is the lower level of a single family residence with separate entrance with views of the Casco Bay Ship Channel. More than simply a bedroom, there is a spacious living room with tv and computer workstation. There is a patio for relaxing as you take in the scenery. We are a short walk to Willard Beach, and we provide beach towels and chairs. There is no kitchen but we provide a coffee maker, and small fridge. Places for take out abound nearby. This is a great getaway for couples.

Guest favourite
A modern living area features a comfortable gray sofa draped with a soft throw. A wooden coffee table sits on a patterned rug, accompanied by a small black side table. A wall-mounted television is positioned against a light-colored wall, with large windows showcasing a view of brick buildings.
Hotel room in Portland
4.93 out of 5 average rating, 229 reviews

Luxury One Bedroom Loft in Portland’s Old Port

Immerse yourself in the culture of the Old Port at your luxury loft. A top choice for travelers, The Docent's Collection was most recently awarded Condé Nast Readers' Choice (2025) and Tripadvisor Travelers' Choice (2025). Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and bedrooms with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team.

Guest favourite
A bright bedroom features a queen bed with an ornate wooden headboard, flanked by two stylish wall lamps. Sliding glass doors provide access to the outdoors, while clerestory windows invite natural light. A cozy rug complements the wooden flooring, enhancing the spacious feel.
Flat in South Portland
4.93 out of 5 average rating, 207 reviews

Sopo Abode

Welcome to your garden oasis. Your home away from home. This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is spacious, calm, and inviting. Have a sit in your private sauna, and take in the abundant birdsong of the neighborhood from your private back patio while you sip your morning coffee. Just down the road (5 minutes) to downtown Portland, Willard Beach, or Knightville, and 10-15 minutes to Scarborough and Cape Elizabeth beaches.

Guest favourite
The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.
Home in Naples
4.98 out of 5 average rating, 187 reviews

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Top guest favourite
A cozy interior features natural wood paneling and beams. Two upholstered chairs are positioned near a large window, allowing light to fill the space. A small bookshelf holds several books, while kitchenware is organized on a nearby shelf. A white stove complements the rustic setting.
Cabin in Bridgton
4.95 out of 5 average rating, 188 reviews

Writers Cabin in the Woods with Sauna!

Nestled in the woods and on Adams Pond with new wood fired sauna! The cabin feels totally hidden away but is less than 10 minutes to Bridgton and Naples, hiking, beaches and restaurants. The woods are beautiful and peaceful and the pond is just down a mossy path. Great for couples or a weekend away. Large deck with grill and outdoor shower, firepit. There is a shared dock on the pond for swimming, fishing, or just enjoying the view as well as a canoe and 2 kayaks, and a paddle board.

Top guest favourite
The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.
Cabin in Freeport
5 out of 5 average rating, 130 reviews

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Guest favourite
The kitchen features modern stainless steel appliances and a spacious countertop with a light wood finish. Bright bay windows allow natural light to illuminate the area. A classic mantle adds a touch of historic charm, while overhead lighting enhances the contemporary design.
Flat in Portland
4.94 out of 5 average rating, 144 reviews

The Margaret at Hawley Marie w/ Parking

Work + play in this modern retreat featuring original architecture with updated amenities. The sunny bay windows flood the living room with light, while the rest of the space benefits from lofty ceilings and an open floor plan. The en suite bathroom has new tiled floor and backsplash, while the kitchen features a beautiful white quartz countertop with stainless appliances. The convenient location and free, private parking is really the cherry on top of this beautiful space!

Top guest favourite
A cozy gas fireplace is featured in a modern living space, surrounded by warm wood accents. Nearby, a comfortable sofa with decorative cushions offers a relaxing spot. The lower left corner shows a unique hanging chair, nestled in a natural environment, enhancing the tranquility of the area.
Flat in South Portland
4.95 out of 5 average rating, 266 reviews

Willard Beach: Cozy Apartment with a King Size Bed

This luxurious first floor apartment is filled with sunshine all day long and on chilly nights the gas fireplace provides a warm ambiance. We think you’ll especially enjoy sinking into the velvet covered king size bed at night and stepping into the spacious shower that includes a rainfall shower head along with a handheld ... use either or both, as you please! The kitchen is equipped with quartz countertops, solid cherry cabinets and high end stainless steel appliances.

Top guest favourite
A spacious sleeping area features natural wood paneling and a high ceiling. A comfortable bed is dressed in light blue and white linens, accompanied by two decorative pillows. A wooden cabinet and a bedside lamp add functional elements, while a window allows soft light to fill the room.
Barn in Portland
5 out of 5 average rating, 471 reviews

Garrison Cove Studio

Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite beverage in one of our comfy Adirondacks.

Top guest favourite
The cozy cabin is illuminated by soft outdoor lights, enhancing its charming facade. The front porch features a seating area, with potted flowers adding a touch of nature. The surrounding grassy area includes stone steps leading towards the entrance, promoting a welcoming atmosphere.
Tiny home in Portland
4.95 out of 5 average rating, 531 reviews

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C in the cabin. Please, no smokers, kids under 7, or guest pets. STHR-000718-2018

Popular amenities for holiday rentals near Portland Head Light