Windham Vacation Rentals

1-24 of 24 rentals
Highland Playhouse

Highland Playhouse

Cabin in Windham, ME

Rating4.42
Persons
7Persons
Bedrooms
3Bedrooms
Bathrooms
2Bathrooms
$259/night
Wellhouse Cottage

Wellhouse Cottage

Cottage in Standish, ME

Rating4.43
Persons
2Persons
Bedrooms
0Bedrooms
Bathrooms
1Bathrooms
$88/night
Loons Nest Cottage

Loons Nest Cottage

Cottage in Standish, ME

Rating4.40
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
1Bathrooms
$158/night
Little Birch on Little Sebago Lake

Little Birch on Little Sebago Lake

Studio in Gray, ME

Rating4.74
Persons
2Persons
Bedrooms
0Bedrooms
Bathrooms
1Bathrooms
$185/night
Super Birch on Little Sebago Lake

Super Birch on Little Sebago Lake

House in Gray, ME

Rating5.00
Persons
14Persons
Bedrooms
3Bedrooms
Bathrooms
4Bathrooms
$1,454/night
Big Birch on Little Sebago Lake

Big Birch on Little Sebago Lake

House in Gray, ME

Rating5.00
Persons
12Persons
Bedrooms
3Bedrooms
Bathrooms
3Bathrooms
$1,079/night
East End Annex

East End Annex

House in Portland, ME

Rating4.53
Persons
2Persons
Bedrooms
1Bedrooms
Bathrooms
1Bathrooms
$137/night
A Foodie’s Delight

A Foodie’s Delight

Condo in Portland, ME

Rating4.50
Persons
4Persons
Bedrooms
1Bedrooms
Bathrooms
1Bathrooms
$200/night
Two Ensuite Historic Portland Charmer

Two Ensuite Historic Portland Charmer

Condo in Portland, ME

Rating4.74
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$272/night
Two Ensuite West End Charmer

Two Ensuite West End Charmer

Condo in Portland, ME

Rating4.85
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$286/night
The Landing on North

The Landing on North

Apartment in Portland, ME

Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
1Bathrooms
$191/night
Pearl of Portland

Pearl of Portland

House in Portland, ME

Rating4.52
Persons
8Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$354/night
Cumberland Casa - A

Cumberland Casa - A

Apartment in Portland, ME

Rating4.13
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
1Bathrooms
$207/night
Cumberland Casa - B

Cumberland Casa - B

Apartment in Portland, ME

Rating4.20
Persons
2Persons
Bedrooms
1Bedrooms
Bathrooms
1Bathrooms
$149/night
Cumberland Charm

Cumberland Charm

Condo in Portland, ME

Rating4.49
Persons
4Persons
Bedrooms
1Bedrooms
Bathrooms
1Bathrooms
$169/night
Morning on the Atlantic

Morning on the Atlantic

Condo in Portland, ME

Rating4.94
Persons
2Persons
Bedrooms
1Bedrooms
Bathrooms
1Bathrooms
$208/night
Four Ensuite The Heart of the West End #3 & #4

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

Condo in Portland, ME

Rating4.80
Persons
8Persons
Bedrooms
4Bedrooms
Bathrooms
4Bathrooms
$740/night
Kilted Pines

Kilted Pines

Cottage in Raymond, ME

Rating4.09
Persons
6Persons
Bedrooms
3Bedrooms
Bathrooms
1Bathrooms
$162/night
Panther Run River Retreat

Panther Run River Retreat

House in Raymond, ME

Rating4.81
Persons
6Persons
Bedrooms
3Bedrooms
Bathrooms
2Bathrooms
$333/night
Blueberry Point

Blueberry Point

House in Raymond, ME

Rating5.00
Persons
10Persons
Bedrooms
3Bedrooms
Bathrooms
2Bathrooms
$655/night
Waterfront Writer's Retreat

Waterfront Writer's Retreat

Studio in Raymond, ME

Rating4.17
Persons
2Persons
Bedrooms
1Bedrooms
Bathrooms
1Bathrooms
$142/night
Tideview Estate

Tideview Estate

House in Cumberland Foreside, ME

Persons
8Persons
Bedrooms
4Bedrooms
Bathrooms
4Bathrooms
$580/night
Charming Hideaway

Charming Hideaway

House in Scarborough, ME

Rating4.86
Persons
6Persons
Bedrooms
2Bedrooms
Bathrooms
2Bathrooms
$278/night
Sebago Shores Cottage

Sebago Shores Cottage

House in Sebago, ME

Rating5.00
Persons
4Persons
Bedrooms
2Bedrooms
Bathrooms
1Bathrooms
$194/night
  • 1-24 of 24
  • 1

© 2026 Casago LLC