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Best Vacation Rentals in Waldoboro - Holiday Lettings - Cabins

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38 Vacation rentals

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Waldoboro ski home to rent.

Waldoboro house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $185 / night

$1,295 / week

1 / 30

Waldoboro Vacation home rental

Waldoboro house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $224 / night

$1,568 / week

1 / 30

Vacation home in Waldoboro

Waldoboro house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $447 / night

$3,129 / week

1 / 22

Waldoboro ski home to rent.

Waldoboro house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $213 / night

$1,491 / week

1 / 30

Vacation home in Waldoboro

Waldoboro house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $244 / night

$1,708 / week

1 / 16

Vacation home in Waldoboro

Waldoboro house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $211 / night

$1,477 / week

1 / 17

Vacation home rental

Waldoboro house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $314 / night

$2,198 / week

1 / 27

Ski home to rent in Waldoboro

Waldoboro house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 6

from $338 / night

$2,366 / week

1 / 30

Vacation home in Waldoboro

Waldoboro house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $299 / night

$2,093 / week

1 / 28

Vacation home in Waldoboro

Waldoboro house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from $224 / night

$1,568 / week

1 / 29

Ski apartment to rent in Waldoboro

Waldoboro apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $389 / night

$2,723 / week

1 / 15

Vacation home rental

Waldoboro house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 4

from $372 / night

$2,604 / week

1 / 30

Ski home to rent in Waldoboro

Waldoboro house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $317 / night

$2,219 / week

1 / 20

Waldoboro Vacation apartment rental

Waldoboro apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $349 / night

$2,443 / week

1 / 28

Ski cottage to rent in Waldoboro

Waldoboro cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from $173 / night

$1,211 / week

1 / 30

Vacation home in Waldoboro

Waldoboro house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $610 / night

$4,270 / week

1 / 30

Ski home to rent in Waldoboro

Waldoboro house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 9

from $409 / night

$2,863 / week

1 / 30

Vacation home in Waldoboro

Waldoboro house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $332 / night

$2,324 / week

1 / 25

Waldoboro Vacation home rental

Waldoboro house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $211 / night

$1,477 / week

1 / 26

Vacation home in Waldoboro

Waldoboro house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $607 / night

$4,249 / week

1 / 15

Waldoboro Vacation home rental

Waldoboro house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $425 / night

$2,975 / week

1 / 30

Waldoboro Vacation home rental

Waldoboro house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $251 / night

$1,757 / week

1 / 27

Home rental in Waldoboro

Waldoboro house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $251 / night

$1,757 / week

1 / 23

Vacation home in Waldoboro

Waldoboro house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $354 / night

$2,478 / week

1 / 30

Waldoboro Vacation home rental

Waldoboro house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from $604 / night

$4,228 / week

1 / 30

Vacation apartment in Waldoboro

Waldoboro apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $504 / night

$3,528 / week

1 / 26

Waldoboro ski home to rent.

Waldoboro house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

from $825 / night

$5,775 / week

1 / 30

Waldoboro Vacation apartment rental

Waldoboro apartment

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 13

from $777 / night

$5,439 / week

1 / 30

Waldoboro Vacation apartment rental

Waldoboro apartment

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 19

from $1,351 / night

$9,457 / week

1 / 30

Vacation home in Waldoboro

Waldoboro house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $891 / night

$6,237 / week

1 / 29

Vacation apartment in Waldoboro

Waldoboro apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $329 / night

$2,303 / week

1 / 30

Vacation apartment in Waldoboro

Waldoboro apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $324 / night

$2,268 / week

1 / 27

Vacation cottage in Waldoboro

Waldoboro cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 7

from $324 / night

$2,268 / week

1 / 30

Waldoboro Vacation cottage rental

Waldoboro cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $512 / night

$3,584 / week

1 / 30

Vacation cottage in Waldoboro

Waldoboro cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $268 / night

$1,876 / week

1 / 30

Apartment rental in Waldoboro

Waldoboro apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $163 / night

$1,141 / week

1 / 14

Home rental in Waldoboro

Waldoboro house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $326 / night

$2,282 / week

1 / 18

Vacation home in Waldoboro

Waldoboro house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

from $250 / night

$1,750 / week

1 / 30

Great rentals within 20 miles that match your search

New Harbor Vacation cottage rental

New Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $436 / night

$3,052 / week

1 / 30

Home rental in Dresden

Dresden house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $182 / night

$1,274 / week

1 / 12