Windham, Maine

Vacation Rentals in Windham, Maine

Discover 29 vacation rental properties in Windham. From 1 to 6 bedrooms. Average $413/night. 100% have pools.

29 verified listings Book securely on VRBO Prices updated March 2026

29 properties available

Brand New Lake Home with Great Sandy beach on Sebago’s Basin

Brand New Lake Home with Great Sandy beach on Sebago’s Basin

3 beds 2 baths
PoolA/CWiFiBalcony
$424/night
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Steps from the beach on Sebago Lake Basin

Steps from the beach on Sebago Lake Basin

2 beds 2 baths
PoolA/CWiFiBalcony
$331/night
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Rise & Shine on Sebago Lake

Rise & Shine on Sebago Lake

6 beds 5 baths
PoolA/CWiFiBalcony
$549/night
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Big Sebago Sandy Beach Sunsets

Big Sebago Sandy Beach Sunsets

2 beds 1 bath
PoolA/CWiFiBalcony
$357/night
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Bright and Peaceful 6 Bedroom Home on Sebago Lake

Bright and Peaceful 6 Bedroom Home on Sebago Lake

6 beds 2 baths
PoolA/CWiFiBalcony
$574/night
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Beautiful Lakefront Family Compound With Dock And Moorings: Stunning Sunsets!

Beautiful Lakefront Family Compound With Dock And Moorings: Stunning Sunsets!

5 beds 2 baths
PoolA/CWiFiBalcony
$538/night
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SALE : DISCOUNTS NOT APPLIED! 7/5-12 8/23-30 7/30- 8/2 Email for Details

SALE : DISCOUNTS NOT APPLIED! 7/5-12 8/23-30 7/30- 8/2 Email for Details

5 beds 3 baths
PoolA/CWiFiBalcony
$941/night
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SEBAGO LAKE HOME WITH WALK OUT SANDY BEACH

SEBAGO LAKE HOME WITH WALK OUT SANDY BEACH

4 beds 2 baths
PoolA/CWiFiBalcony
$998/night
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Stunning, updated home with breathtaking views over Sebago Lake Basin.

Stunning, updated home with breathtaking views over Sebago Lake Basin.

3 beds 2 baths
PoolA/CWiFiBalcony
$414/night
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Lakeside Retreat

Lakeside Retreat

3 beds 2 baths
PoolA/CWiFiBalcony
$349/night
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Cozy Loft - Mountain Views & Sebago Lake Access

Cozy Loft - Mountain Views & Sebago Lake Access

1 bed 1 bath
PoolA/CWiFiBalcony
$117/night
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Sebago Lake Home with Mountain & Lake Views

Sebago Lake Home with Mountain & Lake Views

2 beds 1 bath
PoolA/CWiFiBalcony
$133/night
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Highland Lake House

Highland Lake House

4 beds 2 baths
PoolA/CWiFiBalcony
$442/night
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Cozy 100-year-old Maine camp, steps to Little Sebago Lake

Cozy 100-year-old Maine camp, steps to Little Sebago Lake

3 beds 1 bath
PoolA/CWiFiBalcony
$427/night
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Entire Modern Chic Home in Windham

Entire Modern Chic Home in Windham

2 beds 1 bath
PoolA/CWiFiBalcony
$213/night
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100' of Little Sebago Lake frontage: Enjoy the simple life & endless family fun!

100' of Little Sebago Lake frontage: Enjoy the simple life & endless family fun!

2 beds 2 baths
PoolA/CWiFiBalcony
$269/night
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Cozy Year-round House right outside Portland Maine on Highland Lake.

Cozy Year-round House right outside Portland Maine on Highland Lake.

3 beds 1 bath
PoolA/CWiFiBalcony
$314/night
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Family & dog friendly historic 4BR farmhouse near Sebago Lake w/ boat launch!

Family & dog friendly historic 4BR farmhouse near Sebago Lake w/ boat launch!

4 beds 1 bath
PoolA/CWiFiBalcony
$274/night
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Peaceful Lakeside Oasis Near City Amenities

Peaceful Lakeside Oasis Near City Amenities

3 beds 2 baths
PoolA/CWiFiBalcony
$300/night
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Waterfront on Little Sebago Lake and dog friendly!!

Waterfront on Little Sebago Lake and dog friendly!!

1 bed 1 bath
PoolA/CWiFiBalcony
$279/night
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Sunny Waterfront Family Friendly Little Sebago Home

Sunny Waterfront Family Friendly Little Sebago Home

5 beds 3 baths
PoolA/CWiFiBalcony
$829/night
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Lakefront home with sunrise views, private dock, kayaks, paddle boards, WFH desk

Lakefront home with sunrise views, private dock, kayaks, paddle boards, WFH desk

3 beds 2 baths
PoolA/CWiFiBalcony
$274/night
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4-bedroom Lake-Front Cottage

4-bedroom Lake-Front Cottage

4 beds 1 bath
PoolA/CWiFiBalcony
$241/night
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Lakefront House

Lakefront House

4 beds 2 baths
PoolA/CWiFiBalcony
$462/night
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Pet-friendly! Modern and spacious 3-bedroom home on the Pleasant River.

Pet-friendly! Modern and spacious 3-bedroom home on the Pleasant River.

3 beds 2 baths
PoolA/CWiFiBalcony
$251/night
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Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

3 beds 2 baths
PoolA/CWiFiBalcony
$282/night
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Classic Maine waterfront cottage on pristine Highland Lake Windham/Falmouth

Classic Maine waterfront cottage on pristine Highland Lake Windham/Falmouth

3 beds 1 bath
PoolA/CWiFiBalcony
$458/night
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Waterfront on Highland Lake in Windham

Waterfront on Highland Lake in Windham

4 beds 3 baths
PoolA/CWiFiBalcony
$531/night
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2300 SF, 3 Bdrm, 3.5 Bath Vacation Home Steps from Highland Lake

2300 SF, 3 Bdrm, 3.5 Bath Vacation Home Steps from Highland Lake

3 beds 3 baths
PoolA/CWiFiBalcony
$401/night
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More destinations in Maine

Old Orchard Beach (413) Wells (400) Bar Harbor (311) York (302) Portland (294) Ogunquit (254) Kennebunkport (216) Boothbay Harbor (206) Southwest Harbor (199) Kennebunk (199) Newry (192) Ellsworth (136) Scarborough (132) camden (105) Greenville (104) Harpswell (97) Mount Desert (96) Bethel (94) Mt Desert (64) Boothbay (63)