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Windham Vacation Rentals
1-24 of 29 rentals

Highland Playhouse

$341 avg / night (excludes fees and taxes)
3 Bedrooms | 2 Bath | Sleeps 7

Hawthorne House

$751 avg / night (excludes fees and taxes)
6 Bedrooms | 2 Bath | Sleeps 16

Pine Tree Treat

$407 avg / night (excludes fees and taxes)
3 Bedrooms | 1 Bath | Sleeps 8

Westbrook Hideaway

$388 avg / night (excludes fees and taxes)
3 Bedrooms | 1 Bath | Sleeps 8

Loons Nest Cottage

$215 avg / night (excludes fees and taxes)
2 Bedrooms | 1 Bath | Sleeps 6

Wellhouse Cottage

$131 avg / night (excludes fees and taxes)
0 Bedrooms | 1 Bath | Sleeps 2

Pines Cottage

$283 avg / night (excludes fees and taxes)
2 Bedrooms | 1 Bath | Sleeps 6

Boathouse Cottage

$284 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 4

Super Birch on Little Sebago Lake

$1,345 avg / night (excludes fees and taxes)
3 Bedrooms | 4 Bath | Sleeps 14

Big Birch on Little Sebago Lake

$1,090 avg / night (excludes fees and taxes)
3 Bedrooms | 3 Bath | Sleeps 12

Little Birch on Little Sebago Lake

$197 avg / night (excludes fees and taxes)
0 Bedrooms | 1 Bath | Sleeps 2

East End Annex

$235 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 2

Cumberland Casa - B

$215 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 2

Morning on the Atlantic

$280 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 2

Two Ensuite Historic Portland Charmer

$283 avg / night (excludes fees and taxes)
2 Bedrooms | 2 Bath | Sleeps 4

A Foodie’s Delight

$211 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 4

Two Ensuite West End Charmer

$255 avg / night (excludes fees and taxes)
2 Bedrooms | 2 Bath | Sleeps 4

Cumberland Casa - A

$244 avg / night (excludes fees and taxes)
2 Bedrooms | 1 Bath | Sleeps 6

Cumberland Charm

$199 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 4

Pearl of Portland

$558 avg / night (excludes fees and taxes)
2 Bedrooms | 2 Bath | Sleeps 8

Four Ensuite The Heart of the West End #3 & #4

$771 avg / night (excludes fees and taxes)
4 Bedrooms | 4 Bath | Sleeps 8

Dockside Drift

$561 avg / night (excludes fees and taxes)
4 Bedrooms | 3 Bath | Sleeps 9

Waterfront Writer's Retreat

$146 avg / night (excludes fees and taxes)
0 Bedrooms | 1 Bath | Sleeps 2

Chickadee Cottage

$327 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 6
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