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

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November 2026

December 2026

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Our top choices for Windham vacation homes

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.

1. New and Spacious Family Home Close to Sebago Lake

Standish

SAR 2,795 total

includes taxes & fees

7 Nov - 8 Nov

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

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

North Deering

Patrick J.

SAR 2,888 total

includes taxes & fees

22 Nov - 23 Nov

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

SAR 994 total

includes taxes & fees

19 Nov - 20 Nov

A beach with footprints, a person standing, and birds on the sand.

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

Buxton

Hope T.

SAR 1,219 total

includes taxes & fees

8 Nov - 9 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. Newly Renovated Luxury House with Game Room

Yarmouth

Michelle T.

SAR 2,541 total

includes taxes & fees

9 Nov - 10 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.

SAR 3,783 total

includes taxes & fees

8 Nov - 9 Nov

7. Family, friends, Gathering

Standish

Logan R.

SAR 5,863 total

includes taxes & fees

12 Nov - 13 Nov

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

8. Fully Updated Airy Historic Home in South Freeport

Freeport

boodu

SAR 1,731 total

includes taxes & fees

11 Nov - 12 Nov

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

9. Quiet Spot in lovely Freeport neighborhood

Freeport

SAR 1,433 total

includes taxes & fees

7 Nov - 8 Nov

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

10. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

West End

Susan d.

SAR 1,313 total

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with two wicker chairs and a small round table with a potted plant.

11. Modern & Sunny East End House.

Munjoy Hill

stacey p.

SAR 1,897 total

includes taxes & fees

8 Nov - 9 Nov

A beach with clear water, a sandy shore, and a rocky outcrop with vegetation.

12. Newly Remodeled Cottage with AC- Sebago Lake Area

Raymond

SAR 1,829 total

includes taxes & fees

19 Nov - 20 Nov

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

13. Willard Square Family Home

Willard Beach

David W.

SAR 2,412 total

includes taxes & fees

12 Nov - 13 Nov

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.

14. 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.

SAR 1,493 total

includes taxes & fees

11 Nov - 12 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.

SAR 1,080 total

includes taxes & fees

19 Nov - 20 Nov

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

16. The Barnhouse with hot tub

New Gloucester

Jen V.

SAR 1,277 total

includes taxes & fees

19 Nov - 20 Nov

A multi-story house with a dock and a children's play area.

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

Casco

loie H.

SAR 2,665 total

includes taxes & fees

19 Nov - 20 Nov

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

18. Charming West End Victorian

Parkside

SAR 2,756 total

includes taxes & fees

1 Dec - 2 Dec

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

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

Munjoy Hill

Matt H.

SAR 3,245 total

includes taxes & fees

9 Nov - 10 Nov

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

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

Naples

Gina P.

SAR 2,768 total

includes taxes & fees

19 Nov - 20 Nov

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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 breakfast area with a sign that reads "HAPPY BREAKFAST STARTS HERE" and a coffee machine.

Hampton Inn & Suites Portland West

Nasons Corner

10/10 Excellent

Kyndra

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

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

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

A modern bar area with a wooden bar counter, black bar stools, and a contemporary light fixture.

AC Hotel Portland Downtown/Waterfront, ME

Downtown Portland

10/10 Excellent

Craig

A balcony with wooden flooring, striped cushioned chairs, and a glass railing overlooking a cityscape at night.

Hyatt Place Portland Downtown - Old Port Square

Downtown Portland

10/10 Excellent

Douglas

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

Portland Harbor Hotel

Downtown Portland

10/10 Excellent

Christopher

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