Windham Holiday House Rentals from AU$383: Search Holiday Homes

Windham Holiday Homes
Maine
United States of America
Holiday Homes
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Hotels in Windham Holiday Rentals in Windham Windham Car Hire Windham Holiday Packages

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

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Our top choices for Windham holiday homes

A modern living room with a brown leather sofa, a rustic coffee table, and a dining area with a white table and chairs.

A modern bedroom with a bed, desk, chair, and ottoman.

An outdoor patio with a fire pit, two wooden chairs, and a hammock.

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

1. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts

Windham

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"This is an exceptional property. It was quiet and comfortable, and we all slept well. The location was ideal for our plans and the host answered every question promptly.I highly recommend this rental, and I plan to return."

Richard G.

The price is AU$995

AU$995

includes taxes & fees

30 Sept - 1 Oct

Windham Lakefront: Fire Pit and Modern Comforts

A dirt path in a park with autumn foliage.

A wooden cabin interior with a dining area, a sofa, a kitchen, and large windows.

A rustic cabin with a red door, wooden exterior, and a patio with Adirondack chairs and a table.

A rustic cabin with a red door, surrounded by trees with autumn foliage.

2. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

Westbrook

9.6 out of 10, Exceptional, (43 reviews)

9.6/10

Exceptional

(43 reviews)

"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"

Genevieve W.

The price is AU$811

AU$811

includes taxes & fees

15 Sept - 16 Sept

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

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.

A modern kitchen with a central island, wooden chairs, a bench, and a potted plant.

A two-story house with a central entrance, multiple windows, and a sloped roof.

A modern kitchen with light blue cabinets, a large island, stainless steel appliances, and a hanging pendant light.

3. New and Spacious Family Home Close to Sebago Lake

New and Spacious Family Home Close to Sebago Lake

Standish

The price is AU$1,225

AU$1,225

includes taxes & fees

13 Sept - 14 Sept

New and Spacious Family Home Close to Sebago Lake

A window with a view of a snowy landscape and bare trees.

A kitchen with a stainless steel refrigerator, a built-in oven, a dishwasher, and wooden cabinets.

A house with Christmas lights forming shapes of a reindeer and a sleigh.

A living room with a sofa, coffee table, wooden dining table, and chairs. There are windows with blinds, a ceiling fan, and wall-mounted artwork.

4. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea

Westbrook

The price is AU$451

AU$451

includes taxes & fees

14 Sept - 15 Sept

Tranquility between the Lakes & Sea

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

A cozy living room with a stone fireplace, wooden walls, a ceiling fan, a television, and a large window with blinds.

A bedroom with a bed, wooden walls, a ceiling fan, and a door leading to another room.

A single-story house with a front porch, a small attached garage, and a driveway leading to the house.

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

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

Raymond

The price is AU$386

AU$386

includes taxes & fees

23 Sept - 24 Sept

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

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

A bedroom with a bed, bedside tables, a window, and a ceiling light.

A modern kitchen with stainless steel appliances, white cabinetry, and a wooden dining table with chairs.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a wooden bench.

6. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC

Yarmouth

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"What a beautiful home! Everything about our stay was perfect. The home has everything you could possibly need and more. My family stayed for a long weekend and everyone was so happy with the accommodations. Hoping to go back!"

Lisa L.

The price is AU$1,290

AU$1,290

includes taxes & fees

14 Sept - 15 Sept

Luxe 5 Bed/ 3 Bath with Game Room & AC

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

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

A bedroom with a bed, a nightstand, a wooden dresser, a painting on the wall, and a closet.

A modern kitchen with a bar area, a dining set, and a living room with a TV.

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

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

Buxton

6.0 out of 10, (1 review)

6.0/10

(1 review)

"Place was clean and cozy. Big yard for games and a fire pit for s’mores. Based on previous review I brought pots/pans but didn’t need them. Everything was available. Stove is gas and I was not familiar with using one so that was the only “challenge”We had a ball and the place was perfect for us!!"

Anonymous traveller

The price is AU$461

AU$461

includes taxes & fees

6 Oct - 7 Oct

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

A kitchen with a built-in oven, a sink, and a window with a view of the outdoors.

A living room with a sofa, armchairs, a coffee table, and a patterned rug.

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

A bedroom with a bed, dresser, mirror, and a television.

8. Newly Remodeled Cottage with AC- Sebago Lake Area

Newly Remodeled Cottage with AC- Sebago Lake Area

Raymond

The price is AU$456

AU$456

includes taxes & fees

13 Sept - 14 Sept

Newly Remodeled Cottage with AC- Sebago Lake Area

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

A cozy living room with a wooden ceiling, a dining area with a wooden table and chairs, and a kitchen with wooden cabinets and a hanging light fixture.

A covered porch with a seating area, a small table, and a decorative hanging.

A wooden dining table with benches, a hanging light fixture, and wooden cabinets with glass doors.

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

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

East Deering

10.0 out of 10, Exceptional, (80 reviews)

10/10

Exceptional

(80 reviews)

"Everything was very well stocked!"

Sally O.

The price is AU$1,623

AU$1,623

includes taxes & fees

14 Sept - 15 Sept

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

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

A bedroom with large windows overlooking a lake, a bed, and a chair.

A cozy living room with striped armchairs, a sofa, and a dining table with chairs. Large windows provide natural light and a view of trees outside.

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

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

Casco

9.8 out of 10, Exceptional, (16 reviews)

9.8/10

Exceptional

(16 reviews)

"Our stay at this vacation home was wonderful! We had the best time relaxing and enjoying the fall weather. The property manager was responsive and helpful upon check in and check out. We will most definitely be staying there again!"

Michie K.

The price is AU$1,107

AU$1,107

includes taxes & fees

13 Sept - 14 Sept

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

A compact kitchen with a microwave, coffee maker, and a sink. There are cabinets, a dishwasher, and a dining table with chairs.

A bedroom with a bed, a dresser, a closet, and a window.

A shower area with a white tiled wall, a showerhead, and a curtain with a floral pattern.

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

11. Quiet Spot in lovely Freeport desert pines neighborhood

Quiet Spot in lovely Freeport desert pines neighborhood

Freeport

The price is AU$549

AU$549

includes taxes & fees

17 Sept - 18 Sept

Quiet Spot in lovely Freeport desert pines neighborhood

A modern kitchen with white cabinets, a dining area with a table and chairs, a sofa, and a coffee table with books.

A modern kitchen with white cabinets, a dining table with chairs, and a large window with a view of greenery.

A living room with a fireplace, a television, and large windows.

A dining area with a wooden table and chairs, a television mounted on the wall, and large windows allowing natural light.

12. Fully Updated Lake View Home on Thomas Pond

Fully Updated Lake View Home on Thomas Pond

Casco

The price is AU$731

AU$731

includes taxes & fees

14 Sept - 15 Sept

Fully Updated Lake View Home on Thomas Pond

A two-story house with a balcony, a covered patio, and a fenced yard.

A wooden console table with a wine bottle, glasses, and framed pictures.

A living room with a gray sofa, two pink armchairs, a wooden coffee table, and a colorful rug.

A house with a black front door, white trim, and a number '106' above the door. There are two flower pots on the steps.

13. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries

Munjoy Hill

10.0 out of 10, Exceptional, (105 reviews)

10/10

Exceptional

(105 reviews)

"Everything was as advertised; great accommodations!"

Richard D.

The price is AU$903

AU$903

includes taxes & fees

15 Sept - 16 Sept

The Globe House on Munjoy Hill - Walk to Breweries

A wooden deck with a grill area, overlooking a lake with trees in the background.

A compact kitchen with a central island, wooden flooring, and a mezzanine with a bed.

A small cabin with a covered porch, a deck, and a view of a lake surrounded by trees.

A calm lake with a wooden dock extending into the water.

14. Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse

Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse

Casco

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"An adorable little getaway on the cutest little lake. It is quiet and peaceful."

E Tyler B.

The price is AU$383

AU$383

includes taxes & fees

23 Sept - 24 Sept

Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse

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

A dining room with a wooden table and chairs, a door with a window, and a kitchen in the background.

A backyard with a white wooden fence, a small bush, a white wicker bench, and a stone wall in the background.

A living room with a sofa, coffee table, and a rug. There is a painting on the wall and a window with curtains.

15. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

West End

8.4 out of 10, Very good, (61 reviews)

8.4/10

Very good

(61 reviews)

"Nice place, good location and very responsive host. I would definitely stay again when in Portland."

Susan d.

The price is AU$821

AU$821

includes taxes & fees

11 Oct - 12 Oct

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

A calm lake at dusk with a forested shoreline and a small house with lights on.

16. Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake

Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake

Casco

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Clean and tidy"

Edward R.

The price is AU$416

AU$416

includes taxes & fees

23 Sept - 24 Sept

Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake

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

A bedroom with a bed, dresser, and lamp.

A backyard with a wooden fence, a swing, and a lawn.

A living room with a sofa, coffee table, and a ceiling fan.

17. Willard Square Family Home

Willard Square Family Home

Willard Beach

9.8 out of 10, Exceptional, (12 reviews)

9.8/10

Exceptional

(12 reviews)

"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"

Steve S.

The price is AU$995

AU$995

includes taxes & fees

14 Sept - 15 Sept

Willard Square Family Home

A modern interior with a glass door leading to an outdoor deck with a sofa and a hanging light fixture.

A modern kitchen with a central island, stainless steel appliances, and a skylight.

A loft-style kitchen with a wooden dining table, a built-in oven, and a large window.

A rustic kitchen with wooden walls, a wooden dining table, and a view through a skylight.

18. Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

Oakdale

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Great, renovated set of three units. The location was convenient along with the three parking spots. Window and mini split AC units worked well. The loft space and roof deck on the third floor was particularly nice for hanging out. The ice makers didn’t work and a couple other maintenance issues, but the owner said they would be fixing them. All in, a great space for our family of 11 to explore Portland. "

Andy W.

The price is AU$1,981

AU$1,981

includes taxes & fees

15 Sept - 16 Sept

Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

A storefront with a sign reading "LB KITCHEN" and a window display advertising "MORNING THINGS COFFEE LUNCH BOWLS".

A modern kitchen with a central island, wooden shelves, and a dining area with a colorful rug.

A modern kitchen with a central island, black chairs, and pendant lighting.

19. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.

Munjoy Hill

10.0 out of 10, Exceptional, (43 reviews)

10/10

Exceptional

(43 reviews)

"Overall amazing experience! Property is beautifully maintained. Perfectly located, within walking distance from bakeries, pubs, and restraunts. Host was responsive and helpful."

Jacqui B.

The price is AU$765

AU$765

includes taxes & fees

5 Oct - 6 Oct

Modern & Sunny House Steps from the Promenade.

A cabin with four wooden beds arranged in a U-shape, a wooden door, and windows.

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

A backyard with picnic tables and a red umbrella, overlooking a body of water with boats.

20. ANY BIG PARTY!!!!

ANY BIG PARTY!!!!

Standish

8.0 out of 10, Very good, (2 reviews)

8.0/10

Very good

(2 reviews)

"Beautiful property, spacious, plenty of beds and super easy to get to the lake. Owner was very responsive throughout the process."

Logan R.

The price is AU$2,236

AU$2,236

includes taxes & fees

17 Sept - 18 Sept

ANY BIG PARTY!!!!

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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Top Windham Hotel Reviews

Embassy Suites by Hilton Portland Maine

10/10 Excellent

"Room was a very nice 2 room suite. The staff was very helpful. Breakfast was a nice bonus. Loved the happy hour as a way to start winding down."

Barton 2-night trip

Posted 1 hour ago

Embassy Suites by Hilton Portland Maine

Waves Oceanfront Resort

10/10 Excellent

"It was great stay will do it again"

Jesse 2-night trip

Posted 3 hours ago

Waves Oceanfront Resort

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent

"Cool views on both sides"

Bryan 1-night trip

Posted 10 hours ago

Holiday Inn Portland-By the Bay by IHG

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent

"!"

Cynthia 1-night trip

Posted 15 hours ago

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Cambria Hotel Portland Downtown-Old Port

10/10 Excellent

"Great location and staff was very informative. We stayed one night for an early morning flight but would stay again. Parking was expensive but expected for the area ."

Arlinda 1-night trip

Posted 16 hours ago

Cambria Hotel Portland Downtown-Old Port

Inn at St John Portland In-Town

10/10 Excellent

"unique and special for special people who definitely like an alternative for downtown Portland - and right next to the Doube A Baseball team stadium"

DANIEL 1-night trip

Posted 17 hours ago

Inn at St John Portland In-Town

Clarion Hotel Portland Airport ME

8/10 Good

"Called ahead to confirm reservation and the girl on the phone could not verify. After a lot of checking, she finally found us - not too customer service oriented and spoke poor English. Hotel itself was good and charged what was expected."

Rick 1-night trip

Posted 18 hours ago

Clarion Hotel Portland Airport ME

Grand Beach Inn

10/10 Excellent

"Great relaxing trip but The room needs darkening curtains"

Renee 2-night trip

Posted 18 hours ago

Grand Beach Inn

Portland Regency Hotel & Spa

10/10 Excellent

"Favorite Portland Spot!"

Tegan 1-night trip

Posted 21 hours ago

Portland Regency Hotel & Spa

Find out more about Windham

Windham Holiday Homes information

Number of reviews	372
Accommodation	968 Holiday Homes
Lowest Price	AU$383
Highest Price	AU$2,236

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Windham on Expedia.com

Holiday Homes in Windham

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windham holiday homes

1. Windham Lakefront: Fire Pit and Modern Comforts

2. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

3. New and Spacious Family Home Close to Sebago Lake

4. Tranquility between the Lakes & Sea

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

6. Luxe 5 Bed/ 3 Bath with Game Room & AC

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

8. Newly Remodeled Cottage with AC- Sebago Lake Area

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

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

11. Quiet Spot in lovely Freeport desert pines neighborhood

12. Fully Updated Lake View Home on Thomas Pond

13. The Globe House on Munjoy Hill - Walk to Breweries

14. Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse

15. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

16. Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake

17. Willard Square Family Home

18. Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

19. Modern & Sunny House Steps from the Promenade.

20. ANY BIG PARTY!!!!

Find holiday rentals that suit your style

Top Windham Hotel Reviews

Embassy Suites by Hilton Portland Maine

Find out more about Windham

Windham Holiday Homes information

Explore a world of travel with Expedia