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5 Best Vacation Rentals in Windham - Holiday Lettings - Cabins

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64 Vacation rentals

Vacation cottage in Windham

Windham cottage

2 bedrooms • 1 bathroom • sleeps 7

from $287 / night

$2,004 / week

1 / 26

Windham Vacation condo rental

Windham condo

1 bedroom • 1 bathroom • sleeps 2

from $279 / night

$1,948 / week

1 / 5

Cottage rental in Windham

Windham cottage

2 bedrooms • 1 bathroom • sleeps 6

1 review

from $212 / night

$1,483 / week

1 / 26

Cottage rental in Windham

Windham cottage

2 bedrooms • 1 bathroom • sleeps 6

from $212 / night

$1,483 / week

1 / 27

Vacation cottage in Windham

Windham cottage

3 bedrooms • 1 bathroom • sleeps 6

from $328 / night

$2,293 / week

1 / 26

Windham Vacation condo rental

Windham condo

3 bedrooms • 2 bathrooms • sleeps 8

from $492 / night

$3,439 / week

1 / 8

Great rentals within 20 miles that match your search

Oxford Vacation log cabin rental

Oxford log cabin

3 bedrooms • 2 bathrooms • sleeps 8

3 reviews

from $278 / night

$1,947 / week

1 / 16

Portland Vacation condo rental

Portland condo

1 bedroom • 1 bathroom • sleeps 3

from $327 / night

$2,285 / week

1 / 45

Vacation home in Scarborough

Scarborough house

4 bedrooms • 6 bathrooms • sleeps 10

from $1,145 / night

$8,015 / week

1 / 15

Vacation home in Portland

Portland house

4 bedrooms • 2 bathrooms • sleeps 9

from $659 / night

$7,414 - $9,132 / week

1 / 71

Vacation cottage rental

Sebago cottage

4 bedrooms • 2 bathrooms • sleeps 8

1 review

from $360 / night

$2,519 / week

1 / 14

Vacation tented camp in Limington

Limington tented camp

1 bedroom • 1 bathroom • sleeps 6

from $138 / night

$962 / week

1 / 10

Vacation home with golf nearby in South Portland

South Portland house

4 bedrooms • 3 bathrooms • sleeps 10

from $1,254 / night

$5,697 / week

1 / 78

Cape Elizabeth Vacation home rental

Cape Elizabeth house

5 bedrooms • 4 bathrooms • sleeps 10

from $1,117 / night

$6,842 / week

1 / 77

Vacation home in Long Island

Long Island house

3 bedrooms • 2 bathrooms • sleeps 6

from $344 / night

$2,119 / week

1 / 20

Vacation tented camp in Bridgton

Bridgton tented camp

1 bedroom • 1 bathroom • sleeps 4

from $115 / night

$906 / week

1 / 4

Vacation home in Naples

Naples house

2 bedrooms • 1 bathroom • sleeps 8

from $229 / night

$1,603 / week

1 / 12

Home rental in South Portland

South Portland house

3 bedrooms • 2 bathrooms • sleeps 9

3 reviews

from $796 / night

$3,979 / week

1 / 89

Falmouth Vacation home rental

Falmouth house

3 bedrooms • 1 bathroom • sleeps 6

from $796 / night

$4,552 / week

1 / 42

Falmouth Vacation cottage rental

Falmouth cottage

3 bedrooms • 1 bathroom • sleeps 5

from $344 / night

$2,061 / week

1 / 11

Vacation home in Falmouth

Falmouth house

6 bedrooms • 4 bathrooms • sleeps 13

from $1,145 / night

$12,023 / week

1 / 43

Vacation cottage in Sebago

Sebago cottage

2 bedrooms • 1 bathroom • sleeps 4

3 reviews

from $189 / night

$1,088 / week

1 / 26

Vacation home in Naples

Naples house

3 bedrooms • 1 bathroom • sleeps 10

from $282 / night

$1,972 / week

1 / 12

Vacation cottage in Denmark

Denmark cottage

1 bedroom • 1 bathroom • sleeps 4

6 reviews

from $149 / night

$916 - $1,157 / week

1 / 49

Freeport Vacation home rental

Freeport house

5 bedrooms • 4 bathrooms • sleeps 12

1 review

from $1,002 / night

$6,206 / week

1 / 12

Vacation home in South Freeport

South Freeport house

3 bedrooms • 2 bathrooms • sleeps 6

from $202 / night

$1,411 / week

1 / 30

Cottage rental in Casco

Casco cottage

3 bedrooms • 1 bathroom • sleeps 6

from $271 / night

$1,892 / week

1 / 28

Vacation log cabin in Naples

Naples log cabin

3 bedrooms • 1 bathroom • sleeps 8

from $161 / night

$1,123 / week

1 / 24

Vacation cottage in Denmark

Denmark cottage

5 bedrooms • 2 bathrooms • sleeps 8

from $298 / night

$2,084 / week

1 / 25

Naples Vacation home rental

Naples house

4 bedrooms • 4 bathrooms • sleeps 8

from $610 / night

$4,264 / week

1 / 37

Vacation cottage in Sebago

Sebago cottage

2 bedrooms • 1 bathroom • sleeps 7

1 review

from $180 / night

$1,259 / week

1 / 24

Vacation apartment rental

South Freeport apartment

1 bedroom • 1 bathroom • sleeps 3

from $137 / night

$954 / week

1 / 28

Vacation cottage in Raymond

Raymond cottage

3 bedrooms • 1 bathroom • sleeps 6

from $153 / night

$1,066 / week

1 / 25

Vacation cottage in Sebago

Sebago cottage

1 bedroom • 1 bathroom • sleeps 4

from $147 / night

$1,026 / week

1 / 25

Home rental in Standish

Standish house

3 bedrooms • 2 bathrooms • sleeps 8

from $401 / night

$2,290 / week

1 / 7

Vacation cottage in Limerick

Limerick cottage

4 bedrooms • 1 bathroom • sleeps 6

from $411 / night

$2,878 / week

1 / 37

Long Island Vacation home rental

Long Island house

2 bedrooms • 2 bathrooms • sleeps 6

from $413 / night

$2,886 / week

1 / 24

Freeport Vacation cottage rental

Freeport cottage

1 bedroom • 1 bathroom • sleeps 4

from $355 / night

$2,485 / week

1 / 25

Vacation studio in Sebago

Sebago studio

Studio • 1 bathroom • sleeps 2

from $148 / night

$1,034 / week

1 / 24

Vacation home with shared pool in Limerick

Limerick house

2 bedrooms • 1 bathroom • sleeps 6

from $180 / night

$1,260 / week

1 / 20