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5 Best Vacation Rentals in Windham - Holiday Lettings - Cabins

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65 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

from $177 / night

$1,235 / week

1 / 26

Cottage rental in Windham

Windham cottage

2 bedrooms • 1 bathroom • sleeps 6

from $165 / night

$1,155 / week

1 / 27

Vacation cottage in Windham

Windham cottage

3 bedrooms • 1 bathroom • sleeps 6

from $271 / night

$1,892 / 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

Falmouth Vacation home rental

Falmouth house

3 bedrooms • 1 bathroom • sleeps 6

from $796 / night

$4,552 / week

1 / 42

Vacation home in Scarborough

Scarborough house

4 bedrooms • 6 bathrooms • sleeps 10

from $1,145 / night

$8,015 / week

1 / 15

Home rental in South Portland

South Portland house

3 bedrooms • 2 bathrooms • sleeps 9

from $796 / night

$3,979 / week

1 / 89

Vacation home in Naples

Naples house

2 bedrooms • 1 bathroom • sleeps 8

from $229 / night

$1,603 / week

1 / 12

Vacation home in Portland

Portland house

4 bedrooms • 2 bathrooms • sleeps 9

from $659 / night

$7,414 / week

1 / 71

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

Vacation cottage rental

Sebago cottage

4 bedrooms • 2 bathrooms • sleeps 8

from $360 / night

$2,519 / week

1 / 14

Cape Elizabeth Vacation home rental

Cape Elizabeth house

5 bedrooms • 4 bathrooms • sleeps 10

from $1,117 / night

$6,842 / week

1 / 77

Vacation tented camp in Bridgton

Bridgton tented camp

1 bedroom • 1 bathroom • sleeps 4

from $115 / night

$906 / week

1 / 4

Vacation tented camp in Limington

Limington tented camp

1 bedroom • 1 bathroom • sleeps 6

from $138 / night

$962 / week

1 / 10

Portland Vacation condo rental

Portland condo

1 bedroom • 1 bathroom • sleeps 3

from $327 / night

$2,285 / week

1 / 45

Home rental in Standish

Standish house

3 bedrooms • 2 bathrooms • sleeps 8

from $401 / night

$2,290 / week

1 / 7

Vacation home in Long Island

Long Island house

3 bedrooms • 2 bathrooms • sleeps 6

from $344 / night

$2,119 / week

1 / 20

Vacation apartment rental

South Freeport apartment

1 bedroom • 1 bathroom • sleeps 3

from $148 / night

$1,034 / week

1 / 28

Vacation home in South Freeport

South Freeport house

3 bedrooms • 2 bathrooms • sleeps 6

from $202 / night

$1,411 / week

1 / 30

Vacation apartment rental

Standish apartment

1 bedroom • 1 bathroom • sleeps 2

from $125 / night

$874 / week

1 / 24

Vacation home in Naples

Naples house

3 bedrooms • 1 bathroom • sleeps 10

from $282 / night

$1,972 / week

1 / 19

Freeport Vacation home rental

Freeport house

5 bedrooms • 4 bathrooms • sleeps 12

from $1,002 / night

$6,206 / week

1 / 12

Vacation home in Falmouth

Falmouth house

6 bedrooms • 4 bathrooms • sleeps 13

from $1,145 / night

$8,015 / week

1 / 43

Long Island Vacation home rental

Long Island house

2 bedrooms • 2 bathrooms • sleeps 6

from $413 / night

$2,886 / week

1 / 24

Falmouth Vacation cottage rental

Falmouth cottage

3 bedrooms • 1 bathroom • sleeps 5

from $344 / night

$2,061 / week

1 / 11

Westbrook Vacation home rental

Westbrook house

3 bedrooms • 3 bathrooms • sleeps 6

from $446 / night

$3,118 / week

1 / 27

Vacation home with shared pool in Limerick

Limerick house

2 bedrooms • 1 bathroom • sleeps 6

from $180 / night

$1,260 / week

1 / 20

Vacation home with golf nearby in Falmouth

Falmouth house

4 bedrooms • 3 bathrooms • sleeps 6

from $555 / night

$3,880 / week

1 / 21

Vacation cottage in Denmark

Denmark cottage

1 bedroom • 1 bathroom • sleeps 4

from $149 / night

$916 - $1,157 / week

1 / 49

Vacation guest house in Denmark

Denmark guest house

2 bedrooms • 1 bathroom • sleeps 6

from $144 / night

$916 - $1,157 / week

1 / 49

Vacation cottage in Denmark

Denmark cottage

5 bedrooms • 2 bathrooms • sleeps 8

from $216 / night

$1,507 / week

1 / 25

Freeport Vacation cottage rental

Freeport cottage

1 bedroom • 1 bathroom • sleeps 4

from $355 / night

$2,485 / week

1 / 25

Cottage rental in Casco

Casco cottage

3 bedrooms • 1 bathroom • sleeps 6

from $166 / night

$1,163 / week

1 / 28

Vacation cottage in Limerick

Limerick cottage

4 bedrooms • 1 bathroom • sleeps 6

from $277 / night

$1,940 / week

1 / 37

Cottage rental in Raymond

Raymond cottage

3 bedrooms • 3 bathrooms • sleeps 8

from $343 / night

$2,397 / week

1 / 33

Vacation condo in Bridgton

Bridgton condo

2 bedrooms • 2 bathrooms • sleeps 3

from $179 / night

$1,251 / week

1 / 26

Cottage rental in Poland

Poland cottage

2 bedrooms • 1 bathroom • sleeps 7

from $182 / night

$1,275 / week

1 / 13

Danville Vacation tented camp rental

Danville tented camp

1 bedroom • 1 bathroom • sleeps 10

from $144 / night

$1,139 - $1,684 / week

1 / 15