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Windham Vacation Rentals
1-24 of 29 rentals

Highland Playhouse

$341 avg / night (excludes fees and taxes)
Windham, ME
4.48 (42)
3 Bedrooms | 2 Bath | Sleeps 7

Hawthorne House

$751 avg / night (excludes fees and taxes)
NEW!
Westbrook, ME
1.0 (1)
6 Bedrooms | 2 Bath | Sleeps 16

Pine Tree Treat

$405 avg / night (excludes fees and taxes)
NEW!
Westbrook, ME
3 Bedrooms | 1 Bath | Sleeps 8

Westbrook Hideaway

$386 avg / night (excludes fees and taxes)
NEW!
Westbrook, ME
3 Bedrooms | 1 Bath | Sleeps 8

Loons Nest Cottage

$215 avg / night (excludes fees and taxes)
Standish, ME
4.2 (15)
2 Bedrooms | 1 Bath | Sleeps 6

Wellhouse Cottage

$132 avg / night (excludes fees and taxes)
Standish, ME
4.14 (14)
0 Bedrooms | 1 Bath | Sleeps 2

Boathouse Cottage

$284 avg / night (excludes fees and taxes)
Standish, ME
3.17 (6)
1 Bedrooms | 1 Bath | Sleeps 4

Pines Cottage

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

Little Birch on Little Sebago Lake

$197 avg / night (excludes fees and taxes)
Gray, ME
4.82 (17)
0 Bedrooms | 1 Bath | Sleeps 2

Super Birch on Little Sebago Lake

$1,344 avg / night (excludes fees and taxes)
NEW!
Gray, ME
3 Bedrooms | 4 Bath | Sleeps 14

Big Birch on Little Sebago Lake

$1,090 avg / night (excludes fees and taxes)
Gray, ME
5.0 (2)
3 Bedrooms | 3 Bath | Sleeps 12

East End Annex

$235 avg / night (excludes fees and taxes)
Portland, ME
4.38 (42)
1 Bedrooms | 1 Bath | Sleeps 2

A Foodie’s Delight

$205 avg / night (excludes fees and taxes)
Portland, ME
4.5 (56)
1 Bedrooms | 1 Bath | Sleeps 4

Cumberland Casa - A

$246 avg / night (excludes fees and taxes)
Portland, ME
3.93 (27)
2 Bedrooms | 1 Bath | Sleeps 6

Two Ensuite West End Charmer

$260 avg / night (excludes fees and taxes)
Portland, ME
4.85 (34)
2 Bedrooms | 2 Bath | Sleeps 4

Cumberland Casa - B

$214 avg / night (excludes fees and taxes)
Portland, ME
3.9 (10)
1 Bedrooms | 1 Bath | Sleeps 2

Pearl of Portland

$554 avg / night (excludes fees and taxes)
Portland, ME
4.5 (18)
2 Bedrooms | 2 Bath | Sleeps 8

Morning on the Atlantic

$279 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

$771 avg / night (excludes fees and taxes)
Portland, ME
4.89 (9)
4 Bedrooms | 4 Bath | Sleeps 8

Cumberland Charm

$194 avg / night (excludes fees and taxes)
Portland, ME
4.5 (46)
1 Bedrooms | 1 Bath | Sleeps 4

Two Ensuite Historic Portland Charmer

$288 avg / night (excludes fees and taxes)
Portland, ME
4.87 (39)
2 Bedrooms | 2 Bath | Sleeps 4

Waterfront Writer's Retreat

$145 avg / night (excludes fees and taxes)
Raymond, ME
4.09 (11)
0 Bedrooms | 1 Bath | Sleeps 2

Loon Cove

$637 avg / night (excludes fees and taxes)
Raymond, ME
4.7 (10)
6 Bedrooms | 3 Bath | Sleeps 12

Chickadee Cottage

$326 avg / night (excludes fees and taxes)
Raymond, ME
4.82 (11)
1 Bedrooms | 1 Bath | Sleeps 6
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