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A lighthouse and houses on a rocky coastline with the ocean in the background.

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    Check prices for these dates

    Check prices for these dates, 13 – 14 December 2026

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    Our top choices for Portland holiday homes

    1. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

    A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

    2. Charming West End Victorian

    A wooden covered porch with a green door, potted plants, and a red watering can.

    3. Spacious Portland Home + Parking

    An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

    4. The 87th Townhome by Everrow

    A two-story brick building with a front porch, a black door, and a window with a white frame.

    5. Chic 3-bedroom house in Munjoy Hill with off-street parking.

    A living room with a sofa, coffee table, and a large rug. There is a dining area with chairs and a table. The room has a mural on the wall depicting a landscape.

    6. Modern & Sunny East End House.

    A storefront with the sign 'OYSTERS' and a 'RAW BAR' sign above the entrance. There are outdoor seating areas with tables and chairs.

    7. Spacious 4-bedroom house located in the heart of Portland, ME.

    A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

    8. Willard Square Family Home

    A building named Willard Square with a storefront and a red vehicle parked outside.

    9. Steps to Old Port, balcony, private outdoor space

    Private kitchen

    10. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

    A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

    11. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

    A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

    12. Charming Historic Estate | In-town location

    A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

    13. Quiet Spot in lovely Freeport neighborhood

    A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

    14. Fully Updated Airy Historic Home in South Freeport

    A living room with a sofa, armchair, wooden coffee table, and a potted plant.

    15. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

    A covered porch with a view of a lake and trees.

    16. Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

    A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

    17. Upscale OOB Beach House ♦ Seasonal Heated Pool

    Kitchen and center island

    18. Orchid Harbor, Bailey Island 3BR

    A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

    19. Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi

    A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

    20. Seaside Retreat by Everrow

    A narrow hallway with white walls, a blue carpet, and a door leading outside.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Portland and related destinations

    Stroll along the waterfront, savouring fresh lobster rolls before hopping a Casco Bay Lines ferry to explore nearby islands. Immerse yourself in culture at Portland Museum of Art, then catch live music at the historic State Theatre or Merrill Auditorium.

    See all hotels in Portland

    A lighthouse and houses on a rocky coastline with the ocean in the background.

    Top reviews in Portland

    The Weldon Hotel

    A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

    The Docent's Collection at 121 Middle Street

    A spacious living room with a large dining table, comfortable seating, and large windows offering views of the city.

    Blind Tiger Portland – Carleton Street

    A well-lit living room with a fireplace, comfortable seating, and a large mirror.

    Blind Tiger Portland - Danforth Street.

    A spacious kitchen with a central island, wooden bar stools, and a long dining table.

    Hilton Garden Inn Portland Downtown Waterfront

    A waterfront marina with boats docked, buildings with multiple windows, and a red building with a visible restaurant.

    Inn By The Sea

    A backyard with a fire pit, wooden chairs, and a house with a porch.

    West End Collection at 146 Pine

    Exterior

    Portland Regency Hotel & Spa

    A balcony with a table and chairs, overlooking a street with buildings and parked cars.

    Kennebunkport Captains Collection

    A spacious living room with a fireplace, white walls, and a large window.

    The Press Hotel, Marriott Autograph Collection

    A modern interior with a bar area, seating, and shelves with plants and books.

    Homewood Suites by Hilton Portland

    A hotel with a large entrance, stone pillars, and a sign reading "Homewood Suites Hilton".

    The Francis

    A brick building with a white entrance and the name "THE FRANCIS" above the door.

    HomeAwhile

    A gym with treadmills, elliptical machines, and exercise balls, large windows, and a modern ceiling design.

    Cambria Hotel Portland Downtown-Old Port

    A rooftop terrace with a modern outdoor seating area, a fire pit, and a view of the cityscape.