Chalets in Windham
Maine
United States of America
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A white church with a steeple and red accents, surrounded by autumn trees.

Search Chalets in Windham from CA $230

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your current months are November, 2026 and December, 2026.

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A wooden deck with a checkered mat, two wooden chairs, and a table.

A cabin with a porch, a deck, and a fenced area.

A modern living room with a stone fireplace, a round dining table, and a bright orange sofa.

A cabin with a porch, a deck, and a covered area with a table and chairs.

1. Relaxing A-Frame with Hot Tub and Lake Access

Relaxing A-Frame with Hot Tub and Lake Access

Denmark

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Great house, we had a wonderful time!"

Alex F.

The price is CA $231

CA $231

CA $615 total

includes taxes & fees

Nov 8 - Nov 9

Relaxing A-Frame with Hot Tub and Lake Access

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.

View all properties

Learn more about Windham

Outdoor enthusiasts flock to Dundee Park's sandy beach for swimming and picnicking on Pleasant River's shores. Windham's historic district reveals 19th-century charm, while nearby Sebago Lake State Park offers prime fishing and boating.

See all hotels in Windham

Top reviews in Windham

A multi-story building with a sign reading "Embassy Suites." There is a parking lot with marked handicapped spaces and a white van parked in front.

A chef in a black uniform and white hat, holding a ladle and a bowl, with various dishes in front of him.

A spacious lobby with multiple seating areas, a fireplace, and large windows.

A brick building with a sign reading "WAYPOINT" and outdoor seating with tables, chairs, and a fire pit.

Embassy Suites by Hilton Portland Maine

Portland

10/10 Excellent

Rien à dire

Suke Diadibwa

Reviewed August 27, 2026Reviewed August 27, 2026

Embassy Suites by Hilton Portland Maine

A modern hotel with a prominent sign, a landscaped entrance, and a parking area.

A spacious dining area with a long table, multiple chairs, and a sofa.

A hotel room with a bed, desk, chair, TV, and artwork on the walls.

A reception desk with a wooden design and a welcome sign for the Lobster State.

Hampton Inn & Suites Portland West

Nasons Corner

10/10 Excellent

What a beautiful spot to stay and would come back anytime I’m through this area! A+++

Mark

Reviewed May 23, 2026Reviewed May 23, 2026

Hampton Inn & Suites Portland West

A black SUV parked in front of AC Hotel Portland, a modern building with a brick facade and large windows.

A hotel room with a large bed, a sofa, a small table, and a bench. There is a window with a view of the water.

A modern reception area with a central desk, seating arrangements, and large windows offering views of the cityscape.

A modern living room with a sofa, two armchairs, a glass coffee table, and a decorative wall panel.

AC Hotel Portland Downtown/Waterfront, ME

Downtown Portland

10/10 Excellent

Nice hotel! Room was clean and the hotel is well located.

Nicole Emily Elizabeth

Reviewed August 22, 2026Reviewed August 22, 2026

AC Hotel Portland Downtown/Waterfront, ME

A multi-story hotel with a modern design, featuring a flat roof and large windows.

A hotel room with two beds, a desk, a TV, and a view of a body of water.

A large indoor swimming pool with clear water, tiled flooring, and a seating area with chairs and a plant.

A spacious lobby with a high ceiling, large chandeliers, and a mix of seating areas including sofas and armchairs.

Hilton Garden Inn Portland Downtown Waterfront

Downtown Portland

10/10 Excellent

We had a great hotel experience

Stephane

Reviewed July 31, 2026Reviewed July 31, 2026

Hilton Garden Inn Portland Downtown Waterfront

A Holiday Inn Express hotel with a parking lot, multiple vehicles, and a clear sky.

A swimming pool with lounge chairs and a sunset view.

A hotel room with a bed, bedside table, TV, and a kitchenette in the background.

A buffet with various food items, including omelets and other dishes, displayed in stainless steel containers.

Holiday Inn Express Hotel & Suites South Portland by IHG

South Portland

10/10 Excellent

Friendly staff. Clean hotel

Joanne

Reviewed March 22, 2025Reviewed March 22, 2025

Holiday Inn Express Hotel & Suites South Portland by IHG

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

An indoor swimming pool with a hot tub, lounge chairs, and a sign indicating no diving and no lifeguard on duty.

A hotel lobby with a reception desk, patterned armchairs, a round wooden coffee table, and a fireplace.

A hotel lobby with seating areas, a bar, and a view of the outdoors.

Homewood Suites by Hilton Portland

Scarborough

10/10 Excellent

Quick and easy check in process, staff was very friendly and accommodating, room was clean and comfortable, pool water was SO WARM which was wonderful and the hot tub was at the perfect temp as well! Will definitely stay here again!

Jamie

Reviewed January 2, 2026Reviewed January 2, 2026

Homewood Suites by Hilton Portland

The exterior of a Courtyard by Marriott hotel with a glass entrance, outdoor seating area, and a stone facade.

A bar area with a brick wall, bar stools, and a leather sofa.

A hotel room with a large bed, a desk with a computer, a TV, and a view of the city and water.

A modern bar area with leather seating, a bar counter, and a menu board.

Courtyard Portland Downtown/Waterfront

Downtown Portland

10/10 Excellent

Location

Stacey

Reviewed April 26, 2026Reviewed April 26, 2026

Courtyard Portland Downtown/Waterfront

A multi-story hotel with a prominent entrance, large windows, and a classic architectural design.

A fire pit surrounded by wicker chairs in a garden setting.

A spacious living area with large windows, a staircase, and modern furniture.

A hotel room with a large bed, two bedside tables, a chair, a window with curtains, and a view of the city.

Portland Harbor Hotel

Downtown Portland

10/10 Excellent

We absolutely loved this hotel. The location was perfect for our ladies trip. The staff were beyond helpful!!! And the rooms were very well maintained. thank you very much…..

Barbara

Reviewed September 28, 2026Reviewed September 28, 2026

Portland Harbor Hotel

A modern hotel with a covered entrance, large windows, and a landscaped driveway.

A modern hotel room with a large window, a dining area with a wooden table and chairs, and a sofa with colorful pillows.

A modern kitchen with a central island, bar stools, a flat-screen TV, and wine bottles on shelves.

A modern kitchen with a bar area, bar stools, and a television.

Hilton Garden Inn Portland Airport

Portland

10/10 Excellent

Easy off highway access

alma

Reviewed June 28, 2026Reviewed June 28, 2026

Hilton Garden Inn Portland Airport

A Courtyard by Marriott hotel with a modern design, featuring a brick facade, multiple windows, and a covered entrance area.

A modern indoor swimming pool with clear water, a diving board, and a sunlit area with lounge chairs.

An outdoor patio area with tables and chairs, a large umbrella, and a brick fireplace.

A modern bar area with a counter, stools, and a menu display.

Courtyard by Marriott Portland Airport

South Portland

10/10 Excellent

My kids went to the pool late, but the staff allowed them to swim until 12 midnight..

Maria Concepcion

Reviewed July 19, 2026Reviewed July 19, 2026

Courtyard by Marriott Portland Airport

A hotel entrance with a glass door, a column, and potted plants.

A swimming pool with lounge chairs and tables, indoor lighting, and a ceiling with ventilation.

A conference room with a stage featuring a large screen displaying the word 'Float' and a banner for the University of Maine.

A large conference room with round tables, chairs, and a podium.

Holiday Inn Portland-By the Bay by IHG

Downtown Portland

10/10 Excellent

Le service déjeunés étais parfait et tous est facile d’accès

Donovan

Reviewed August 20, 2026Reviewed August 20, 2026

Holiday Inn Portland-By the Bay by IHG

A black front door with a light fixture above it, flanked by two potted evergreen trees.

A dining area with a round table set for six, surrounded by wooden chairs. A chandelier hangs above, and a white door with an exit sign is visible in the background.

A coastal landscape with a sandy beach, rocky outcrops, and grassy dunes.

A breakfast setup with a tiered tray holding fruits, cups, and a coffee pot.

The Orchard House: Inn & Cafe

Freeport

10/10 Excellent

Beautiful place. Rooms were exceptionally lovely. Staff also!

Janne

Reviewed June 26, 2022Reviewed June 26, 2022

The Orchard House: Inn & Cafe

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Search Chalets in Windham from CA $230

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Windham chalets

1. Relaxing A-Frame with Hot Tub and Lake Access

Learn more about Windham

Top reviews in Windham

Embassy Suites by Hilton Portland Maine

10/10 Excellent

Explore a world of travel with Expedia