Windsor Vacation Rentals, Houses & More


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Areas near Windsor

Great rentals within 30 miles that match your search

1 / 14

Holiday home sea

  • 4
  • 4
  • 2 nights min

$99

Details

1 / 16

Reysol- Costa Saracena

  • 2
  • 7
  • Min stay varies

$151

Details

1 / 16

Pepin Summer Cottage-Family Friendly & Affordable!

  • 2
  • 10
  • 7 nights min

$125

Details

20
1 / 8

Lake Front Cottage

  • 4
  • 8
  • Min stay varies

$125

Details

1 / 29

Rustic Lakeside Lodge and Cabins

  • 10
  • 26
  • 7 nights min

$772

Details

1 / 11

Lake Front Housekeeping Cottage B

  • 3
  • 6
  • 7 nights min

$129

Details

1 / 6

Lake View Housekeeping Cottage C

  • 1
  • 2
  • 7 nights min

$100

Details

1 / 9

Lake Front Housekeeping Cottage

  • 2
  • 4
  • 7 nights min

$122

Details

6
1 / 32

Moon Loon, Lakefront Cottage, Lake St. George

  • 2
  • 6
  • 1 night min

$195

Details

8
1 / 3

Waterfront vacation home--fully equipped

  • 3
  • 6
  • 7 nights min

$160

Details

1
1 / 46

Maple Hill Farm Inn

  • 8
  • 19
  • 1 night min

$150

Details

1 / 22

THE BAXTER | JEFFERSON MAINE | PET FRIENDLY | DAMARISCOTTA LAKE | INCREDIBLE

  • 2
  • 6
  • Min stay varies

$205

Details

1 / 29

Rustic lakefront home w/ private dock, wood fireplace & modern conveniences

  • 5
  • 9
  • Min stay varies

$99

Details

1 / 26

Loon Call Cabin

  • 3
  • 10
  • Min stay varies

$189

Details

1 / 17

Brand New Maine Camp

  • 4
  • 8
  • Min stay varies

$169

Details

1
1 / 21

Damariscotta Lake Cottage - Jefferson, Maine

  • 2
  • 6
  • 3 nights min

$218

Details

3
1 / 10

The Lake House On Great Pond

  • 3
  • 8
  • Min stay varies

$200

Details

1 / 37

Gorgeous Lakefront Cottage on Cobbessee Lake near Lighthouse

  • 3
  • 10
  • 7 nights min

$215

Details

1 / 29

Exceptionally cute lakefront cabin w/ stunning views & dock - dogs ok!

  • 3
  • 6
  • 2 nights min

$80

Details

1
1 / 35

Newly restored, watefront cottage w/ private dock, fireplace and farm - dogs OK

  • 2
  • 6
  • Min stay varies

$83

Details

1 / 25

Lakefront home w/ incredible views, a private dock, deck & water slide!

  • 3
  • 7
  • Min stay varies

$81

Details

3
1 / 22

Charming Lakefront Cabin, Great View, Private Dock

  • 3
  • 8
  • 7 nights min

$186

Details

1 / 20

The Barn

  • 3
  • 12
  • 7 nights min

$300

Details

1 / 24

NEW! 3BR Oakland Cottage - 100ft From The Water!

  • 3
  • 7
  • Min stay varies

$75

Details

1
1 / 20

Villa on Cobbossee Lake, private beach, lake view,

  • 3
  • 8
  • 7 nights min

$507

Details

1 / 31

Secluded lake front home

  • 4
  • 8
  • 1 night min

$225

Details

10
1 / 16

Cobbossee Lake House Rental, Winthrop, Maine

  • 3
  • 6
  • 7 nights min

$230

Details

1 / 24

Little Tree Cottage

  • 2
  • 5
  • 7 nights min

$172

Details

1 / 24

Updated 3BR Cabin on Maranacook Lake w/Private Dock, and Wrap Around Deck and

  • 3
  • 8
  • Min stay varies

$250

Details

6
1 / 12

West Gardiner Vacation Rental cabin

  • 1
  • 3
  • Min stay varies

$100

Details

1 / 9

Beautiful Pemaquid Lake Cottage

  • 3
  • 6
  • 7 nights min

$250

Details

1 / 13

Damariscotta Lake

  • 1
  • 6
  • 5 nights min

$275

Details

1 / 15

Lakefront on Lake Cobbossee, 5 Bedrooms, BEAUTIFUL VIEWS

  • 5
  • 11
  • 7 nights min

$286

Details

2
1 / 12

Peaceful Lakefront Cottage on Beautiful Long Pond

  • 3
  • 6
  • 7 nights min

$200

Details

1
1 / 29

Beautiful Maine Get Away

  • 3
  • 8
  • Min stay varies

$150

Details

1
1 / 19

Belgrade Me lake front

  • 3
  • 8
  • 4 nights min

$500

Details

1 / 24

Waterfront Storybook Maine Farmhouse – Wildflower Fields & Rolling Hills

  • 3
  • 6
  • Min stay varies

$194

Details

1 / 24

NEW! Lakefront 2BR Winthrop Home w/Elevated Deck!

  • 2
  • 4
  • Min stay varies

$130

Details

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