
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.

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.

Luxury Year-round Hobbit House w/ private hot tub
Fern Hollow is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

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.

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.

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!

Higgins Beach *New* Beach Home & Private Offices
Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

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!

Peaks Island Master Bedroom Suite
Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

Cape Elizabeth Garden Apt+Beach+Close to Portland!
Bright, airy, two-story, 1000 sf apartment, with view of gardens. Off-street parking and private entrance. First floor living area with kitchenette, and sofa-bed, for additional guests. Second floor king bedroom with full bath. Ideally located a short walk to Kettle Cove Beach, and just minutes from Two Lights State Park, Crescent Beach, Higgins Beach and Robinson Woods Trail. Portland - voted the best restaurant city in the US - is a 10 minute drive. STR Permit #210701.

Old Port Penthouse Suite - Amazing Harbor Views
CO2024-01992 Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quiet + Secure. Gorgeous contemporary suite full of light located right across from the working waterfront. Lobster and seafood off the boat is 100 meters from your front door. Watch the ferries to the islands from the cupola. Smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

HotTub/5min to K-port, Pet friendly, @anchorunwind
Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."

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!
Popular amenities for holiday rentals near Portland Head Light
Condo rentals with Wi-Fi

Luxury Beach Front Condo! Prime Location!

⭐️✨⭐️ West End Old Port CLEAN, cozy, convenient

First Floor Portland Condo 3 Bed 2 Bath + Parking

Penthouse, Walk To The Old Port & The Beach!

Walk to Top Dining • Boutique Stay • Parking

Mary J. Eastburn House - Baxter Suite

Renovated Exchange St. Loft w/Free Parking

Rustic Willard Beach condo ten mins from Old Port!
Family-friendly house rentals

Wren Cabin + Wood fired Sauna

Stone Isle. 8 acres next 2 little john preserve.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Modern Peaks Island Getaway | Ocean Views + Decks

Explore Portland from a 18th-Century Victorian

Modern & Sunny East End House. Private Parking!

"Periwinkle" ~ a Charming Oceanfront Cottage

Entire Ideally Located Private Cape Elizabeth Home
Apartment rentals with air conditioning

Portland + Cape Elizabeth + Beaches + luxurious!

Welcome to our BoHo Treehouse! Beaches/Portland

Cozy South Portland studio with King bed! REG107

Modern Studio Loft w/ Parking in Perfect Location

Cozy SoPo Condo

Studio Apt, 7 mins to Downtown, Parking, Café

Luxury Retreat In Back Cove | 10 Min to Downtown

The Howard on Munjoy Hill
Other great holiday rentals near Portland Head Light

Garrison Cove Studio

Apartment Walking Distance to Willard Beach

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit

The Garden Cabin Tiny Home

Yurt on Chebeague Island

Old Port Loft - 301

1BR Apartment w/ Private Sauna Near Beach

The Nest
Destinations to explore
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Willard Beach
- Scarborough Beach
- Short Sands Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- East End Beach
- Footbridge Beach
- Popham Beach State Park
- Cape Neddick Beach
- Coastal Maine Botanical Gardens
- Gooch's Beach
- King Pine Ski Area
- Hills Beach
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Pleasant Mountain Ski Area
- Fortunes Rocks Beach
- Funtown Splashtown USA





