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Windham Vacation Rentals
1-24 of 28 rentals

Highland Playhouse

$335 avg / night (excludes fees and taxes)
3 Bedrooms | 2 Bath | Sleeps 7

Hawthorne House

$760 avg / night (excludes fees and taxes)
6 Bedrooms | 2 Bath | Sleeps 16

Pine Tree Treat

$410 avg / night (excludes fees and taxes)
3 Bedrooms | 1 Bath | Sleeps 8

Westbrook Hideaway

$391 avg / night (excludes fees and taxes)
3 Bedrooms | 1 Bath | Sleeps 8

Loons Nest Cottage

$202 avg / night (excludes fees and taxes)
2 Bedrooms | 1 Bath | Sleeps 6

Wellhouse Cottage

$132 avg / night (excludes fees and taxes)
0 Bedrooms | 1 Bath | Sleeps 2

Boathouse Cottage

$285 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 4

Pines Cottage

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

Little Birch on Little Sebago Lake

$201 avg / night (excludes fees and taxes)
0 Bedrooms | 1 Bath | Sleeps 2

Super Birch on Little Sebago Lake

$1,500 avg / night (excludes fees and taxes)
3 Bedrooms | 4 Bath | Sleeps 14

Big Birch on Little Sebago Lake

$1,200 avg / night (excludes fees and taxes)
3 Bedrooms | 3 Bath | Sleeps 12

A Foodie’s Delight

$206 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 4

East End Annex

$243 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 2

Cumberland Casa - A

$276 avg / night (excludes fees and taxes)
2 Bedrooms | 1 Bath | Sleeps 6

Cumberland Charm

$193 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 4

Two Ensuite West End Charmer

$314 avg / night (excludes fees and taxes)
2 Bedrooms | 2 Bath | Sleeps 4

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

$729 avg / night (excludes fees and taxes)
4 Bedrooms | 4 Bath | Sleeps 8

Pearl of Portland

$562 avg / night (excludes fees and taxes)
2 Bedrooms | 2 Bath | Sleeps 8

Cumberland Casa - B

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

Morning on the Atlantic

$288 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 2

Two Ensuite Historic Portland Charmer

$316 avg / night (excludes fees and taxes)
2 Bedrooms | 2 Bath | Sleeps 4

Loon Cove

$901 avg / night (excludes fees and taxes)
6 Bedrooms | 3 Bath | Sleeps 12

Waterfront Writer's Retreat

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

Chickadee Cottage

$336 avg / night (excludes fees and taxes)
1 Bedrooms | 1 Bath | Sleeps 6
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