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Windham Vacation Rentals
1-24 of 29 rentals

Highland Playhouse

$337 avg / night (excludes fees and taxes)
Windham, ME
4.46 (39)
3 Bedrooms | 2 Bath | Sleeps 7

Westbrook Hideaway

$392 avg / night (excludes fees and taxes)
NEW!
Westbrook, ME
3 Bedrooms | 1 Bath | Sleeps 8

Hawthorne House

$760 avg / night (excludes fees and taxes)
NEW!
Westbrook, ME
1.0 (1)
6 Bedrooms | 2 Bath | Sleeps 16

Pine Tree Treat

$411 avg / night (excludes fees and taxes)
NEW!
Westbrook, ME
3 Bedrooms | 1 Bath | Sleeps 8

Loons Nest Cottage

$203 avg / night (excludes fees and taxes)
Standish, ME
4.2 (15)
2 Bedrooms | 1 Bath | Sleeps 6

Wellhouse Cottage

$133 avg / night (excludes fees and taxes)
Standish, ME
4.14 (14)
0 Bedrooms | 1 Bath | Sleeps 2

Pines Cottage

$283 avg / night (excludes fees and taxes)
Standish, ME
4.27 (11)
2 Bedrooms | 1 Bath | Sleeps 6

Boathouse Cottage

$285 avg / night (excludes fees and taxes)
Standish, ME
3.17 (6)
1 Bedrooms | 1 Bath | Sleeps 4

Super Birch on Little Sebago Lake

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

Little Birch on Little Sebago Lake

$201 avg / night (excludes fees and taxes)
Gray, ME
4.82 (17)
0 Bedrooms | 1 Bath | Sleeps 2

Big Birch on Little Sebago Lake

$1,200 avg / night (excludes fees and taxes)
Gray, ME
5.0 (2)
3 Bedrooms | 3 Bath | Sleeps 12

East End Annex

$245 avg / night (excludes fees and taxes)
Portland, ME
4.35 (40)
1 Bedrooms | 1 Bath | Sleeps 2

Cumberland Casa - A

$276 avg / night (excludes fees and taxes)
Portland, ME
4.0 (26)
2 Bedrooms | 1 Bath | Sleeps 6

Two Ensuite West End Charmer

$334 avg / night (excludes fees and taxes)
Portland, ME
4.85 (34)
2 Bedrooms | 2 Bath | Sleeps 4

Cumberland Casa - B

$216 avg / night (excludes fees and taxes)
Portland, ME
3.89 (9)
1 Bedrooms | 1 Bath | Sleeps 2

Two Ensuite Historic Portland Charmer

$331 avg / night (excludes fees and taxes)
Portland, ME
4.87 (38)
2 Bedrooms | 2 Bath | Sleeps 4

A Foodie’s Delight

$206 avg / night (excludes fees and taxes)
Portland, ME
4.48 (54)
1 Bedrooms | 1 Bath | Sleeps 4

Cumberland Charm

$204 avg / night (excludes fees and taxes)
Portland, ME
4.53 (43)
1 Bedrooms | 1 Bath | Sleeps 4

Pearl of Portland

$566 avg / night (excludes fees and taxes)
Portland, ME
4.53 (17)
2 Bedrooms | 2 Bath | Sleeps 8

Morning on the Atlantic

$290 avg / night (excludes fees and taxes)
Portland, ME
4.92 (25)
1 Bedrooms | 1 Bath | Sleeps 2

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

$731 avg / night (excludes fees and taxes)
Portland, ME
4.88 (8)
4 Bedrooms | 4 Bath | Sleeps 8

Chickadee Cottage

$342 avg / night (excludes fees and taxes)
Raymond, ME
4.82 (11)
1 Bedrooms | 1 Bath | Sleeps 6

Waterfront Writer's Retreat

$147 avg / night (excludes fees and taxes)
Raymond, ME
4.0 (10)
0 Bedrooms | 1 Bath | Sleeps 2

Loon Cove

$901 avg / night (excludes fees and taxes)
Raymond, ME
4.7 (10)
6 Bedrooms | 3 Bath | Sleeps 12
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