A white church with a steeple and red accents, surrounded by autumn trees.

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Dates

November 2026

December 2026

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Our top choices for Windham vacation homes

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

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

Windham

Michael S.

AED 2,355 total

includes taxes & fees

17 Nov - 18 Nov

A dining area with a long wooden table, six chairs, and a bench. There are large windows with curtains, a plant, and a view into another room.

2. New and Spacious Family Home Close to Sebago Lake

Standish

A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

3. Cozy 2-bedroom house with shared beach access to Sebago Lake

Raymond

AED 973 total

includes taxes & fees

18 Nov - 19 Nov

A covered wooden deck with a view of a building's exterior.

4. Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Buxton

Hope T.

AED 1,193 total

includes taxes & fees

25 Nov - 26 Nov

A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

5. Heated Game Room, Coastal Maine Cape Sleeps 10

Yarmouth

Michelle T.

AED 3,520 total

includes taxes & fees

16 Nov - 17 Nov

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

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

East Deering

Mike G.

AED 3,899 total

includes taxes & fees

12 Nov - 13 Nov

A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

7. Family, friends, Gathering

Standish

Logan R.

AED 5,737 total

includes taxes & fees

12 Nov - 13 Nov

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

8. Quiet Spot in lovely Freeport neighborhood

Freeport

AED 1,259 total

includes taxes & fees

12 Nov - 13 Nov

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

9. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

West End

Susan d.

AED 1,267 total

includes taxes & fees

16 Nov - 17 Nov

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

10. Fully Updated Airy Historic Home in South Freeport

Freeport

boodu

AED 1,694 total

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with a central island, a dining area with a sofa and chairs, and a living room with a colorful rug and plants.

11. Modern & Sunny East End House.

Munjoy Hill

stacey p.

AED 1,929 total

includes taxes & fees

12 Nov - 13 Nov

A living room with a sofa, armchair, and coffee table, a kitchen with appliances, and a dining area with chairs.

12. Newly Remodeled Cottage with AC- Sebago Lake Area

Raymond

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.

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

Munjoy Hill

"Wow, wow, wow! My family and I all agree that this has been the best rental home we have ever stayed in. The interior design is so chic, we were truly wowed by the attention to detail in this place. The beds and pillows are also extremely comfy, we all had a great two nights of sleep here. The location of this place is phenomenal, it neighbors the Portland Observatory, many bars/cafes, and is a short walk down to the eastern promenade. We will absolutely stay here again the next time we’re in...

Maris P.

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

14. Willard Square Family Home

Willard Beach

David W.

AED 2,360 total

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with a wooden dining table, a ceiling fan, and a view of the outdoors.

15. Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

Casco

Edward R.

AED 1,065 total

includes taxes & fees

18 Nov - 19 Nov

A lakeside property with a dock, inflatable raft, and a house with a balcony.

16. Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

Casco

loie H.

AED 2,632 total

includes taxes & fees

10 Dec - 11 Dec

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

17. Charming West End Victorian

Parkside

AED 2,556 total

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with a bar area, wooden ceiling, and skylights.

18. The Barnhouse with hot tub

New Gloucester

Jen V.

AED 1,201 total

includes taxes & fees

23 Nov - 24 Nov

A modern cabin with a large glass facade, a hot tub, and wooden steps leading to the entrance.

19. LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

Naples

Gina P.

AED 2,708 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Munjoy Hill

Matt H.

AED 3,175 total

includes taxes & fees

12 Nov - 13 Nov

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 bright room with large windows, two armchairs, a small table, and a chandelier.

Dormir

Windham

10/10 Excellent

Kevin

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

Embassy Suites by Hilton Portland Maine

Portland

10/10 Excellent

Michael

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

Cambria Hotel Portland Downtown-Old Port

Downtown Portland

10/10 Excellent

seth

A spacious hotel lobby with a reception area, seating arrangements, and large windows providing natural light.

Hampton Inn & Suites Portland West

Nasons Corner

10/10 Excellent

Kyndra

A brick building with a red awning labeled "Chateau Riverside."

Portland Regency Hotel & Spa

Downtown Portland

10/10 Excellent

This property is beautiful. It sits in the historic area of the old port. It is very close to the waterfront, restaurants, shops and historic areas. The mattress and sheets were superb. While in the old port, we took a trolley tour which took us out to Portland headlight and then gave us a tour of of the old port. You can catch fairies from about two or three minutes walk away, we would strongly recommend this hotel.

Debra

A modern outdoor seating area with a circular fire pit, surrounded by black wicker chairs and a covered patio.

TownePlace Suites by Marriott Portland Airport ME

South Portland

10/10 Excellent

Karen

An outdoor seating area with a fire feature, comfortable seating, and a view of a waterfront.

Canopy by Hilton Portland Waterfront

Downtown Portland

10/10 Excellent

Noah

A historic building with classical architecture, featuring a prominent tower and ornate columns.

Hyatt Place Portland Downtown - Old Port Square

Downtown Portland

10/10 Excellent

Douglas

A pool table with balls, a sofa, and a dining area with chairs and tables.

Aloft by Marriott Portland Downtown Waterfront ME

Downtown Portland

10/10 Excellent

Andre

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

Craig

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

Hilton Garden Inn Portland Downtown Waterfront

Downtown Portland

10/10 Excellent

Robert

An outdoor patio area with wicker furniture, string lights, and a barbecue grill.

Residence Inn by Marriott Portland Downtown/Waterfront

Downtown Portland

10/10 Excellent

Mark

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

Portland Harbor Hotel

Downtown Portland

10/10 Excellent

Christopher

A grand piano in a spacious room with large windows, leather chairs, and a small table.

The Westin Portland Harborview

Downtown Portland

10/10 Excellent

Lawrence

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

Homewood Suites by Hilton Portland

Scarborough

10/10 Excellent

I love this place! Check in is always smooth and the staff is always friendly. I really like the room set up with the separate living space from the sleeping space, and also a separate full kitchen area. Breakfast is included and always good with a large variety to choose from. They also have a free light supper a few nights a week. I sleep so well as the mattress and pillows are wonderful. The toiletries are nice and the towels are thick. The room was spotless and even though it is a...

Kelli

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

The Weldon Hotel

Downtown Portland

10/10 Excellent

Amazing place to stay in Portland. The location was great. The hotel is right next to Courtyard Marriott and Aloft hotels, but it feels so much more comfortable. The unit was twice as large as a typical Marriott room about 700 sq. ft which was wonderful. It is Walkable to the ferry boat, restaurants and shops. There is a full kitchen, dining area, living area, very large island with large windows to brighten the place and a set of washer and dryer in the unit. Extremely clean and it looked...

Rana