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Holiday Houses in Chestertown

151 Holiday homes

Loon Lake Retreat with Private Dock

Chestertown house

19

  • Beach / lakeside relaxation
  • •  Child friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £179 / night

£1,159 / week

Atateka Point Lodge and Treehouse Guest Cottage

Chestertown cottage

13

  • Beach / lakeside relaxation
  • •  Nearest beach 26 km
  • •  Child friendly
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £379 / night

£2,852 - £3,476 / week

Black Bear Cabin

Chestertown log cabin

16

  • Nearest beach 5 km
  • •  Child friendly
  • •  Private garden
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £134 / night

£847 / week

Friends Lake- Quaint and New

Chestertown cottage

3

  • Beach / lakeside relaxation
  • •  Nearest beach 0.1 km
  • •  Child friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from £178 / night

£1,070 - £1,227 / week

Green Mansions Vacation Condo

Chestertown apartment

17

  • Beach / lakeside relaxation
  • •  Nearest beach 0 km
  • •  Ski
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £134 / night

£713 / week

The Treehouse at Atateka Point Lodge

Chestertown b&b

7

  • Beach / lakeside relaxation
  • •  Child friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £290 / night

£1,964 - £2,401 / week

Cozy cottage with deeded lake rights - 100 steps to the beach

Chestertown house

  • Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £147 / night

£1,023 / week

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £54 / night

£375 / week

Enormous lakefront house with high-end touches, private dock

Chestertown house

  • Child friendly
  • •  Car not necessary
  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

from £599 / night

£4,192 / week

Adorable log home w/ a full kitchen - river frontage close by!

Chestertown house

  • Child friendly
  • •  Car not necessary
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from £64 / night

£443 / week

LOON LAKE luxury Ski Gore,snowmobile,canoe,kayaks

Chestertown house

3

  • Child friendly
  • •  Private garden
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 14

from £269 / night

£1,793 - £1,882 / week

Dog-friendly, lakefront camp cabin w/ a dock & multiple decks

Chestertown house

  • Child friendly
  • •  Car not necessary
  • •  Pet friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £227 / night

£1,585 / week

Family-friendly coastal condo with shared pool, hot tub and easy beach access

Chestertown house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £128 / night

£892 / week

Historic Greek Revival style home w/ screened in porch -near attractions!

Chestertown chateau

  • Child friendly
  • •  Car not necessary
  • •  Air conditioning
  • 6 bedrooms
  • 5 bathrooms
  • sleeps 11

from £163 / night

£1,142 / week

Family-friendly coastal condo with shared pool, hot tub and easy beach access!

Chestertown house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £128 / night

£892 / week

Beautiful lakefront house with dock, beach, multiple decks

Chestertown house

  • Child friendly
  • •  Car not necessary
  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

from £139 / night

£967 / week

Lakefront house with private beach and dock, multiple decks

Chestertown house

  • Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

from £368 / night

£2,577 / week

Charming oceanfront cottage w/enclosed porches steps to the water! Dogs ok!

Chestertown house

  • Child friendly
  • •  Car not necessary
  • •  Pet friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £201 / night

£1,404 / week

Single-level, spacious house with kayaks, lake access nearby

Chestertown house

1

  • Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from £114 / night

£793 / week

Beautiful coastal condo w/ Gulf views, shared pool, hot tub and beach access

Chestertown house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £128 / night

£892 / week

NEW LISTING! Lakefront cabin with sandy beach, dock, multiple fireplaces

Chestertown house

  • Child friendly
  • •  Car not necessary
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

from £388 / night

£2,714 / week

Dog-friendly, lakefront house with 2 living areas, beach nearby

Chestertown house

  • Child friendly
  • •  Car not necessary
  • •  Air conditioning
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £213 / night

£1,491 / week

Gorgeous and spacious beachfront condo with shared pool and beach access

Chestertown house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £89 / night

£618 / week

Great rentals within 20 miles that match your search

3 Bedroom Beach Unit

Lake George apartment

2

  • Beach / lakeside relaxation
  • •  Child friendly
  • •  Air conditioning
  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

from £170 / night

£1,160 / week

Main House 1

Diamond Point house

1

  • Beach / lakeside relaxation
  • •  Air conditioning
  • •  Pet friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £170 / night

£1,047 / week

Cherrybank, an Adirondack house on the lake

Severance house

1

  • Beach / lakeside relaxation
  • •  Child friendly
  • •  Pet friendly
  • 5 bedrooms
  • 2 bathrooms
  • sleeps 6

from £244 / night

£1,703 / week

Adirondack 1-4

Lake George cottage

2

  • Beach / lakeside relaxation
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £157 / night

£977 / week

Grandpa's Cabin

Schroon Lake cottage

  • Child friendly
  • •  Pet friendly
  • •  Private garden
  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £109 / night

£762 - £1,076 / week

Collette's Cottage 1

Lake George cottage

2

  • Child friendly
  • •  Pet friendly
  • •  Private garden
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from £247 / night

£1,703 / week

The Gold Eagle - Cottage 4

Lake George cottage

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £99 / night

£574 - £637 / week

Ash 1-4 Cottage

Lake George house

  • Child friendly
  • •  Air conditioning
  • •  Ask about pets
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £162 / night

£1,013 / week

Lake George Getaway Rental By Million Dollar Beach

Lake George house

3

  • Child friendly
  • •  Air conditioning
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

from £359 / night

£2,510 / week

Green Chalet at Tripp Lake

Warrensburg log cabin

1

  • Beach / lakeside relaxation
  • •  Nearest beach 0.5 km
  • •  Child friendly
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £265 / night

£1,748 / week

The Gold Eagle - Cottage 9

Lake George house

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £108 / night

£596 - £659 / week

The Gold Eagle - Cottage 5

Lake George cottage

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £117 / night

£632 - £883 / week

Main House 1 & 2

Lake George house

1

  • Beach / lakeside relaxation
  • •  Child friendly
  • •  Air conditioning
  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

from £332 / night

£1,972 / week

Main House 2

Diamond Point house

  • Beach / lakeside relaxation
  • •  Child friendly
  • •  Air conditioning
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £170 / night

£1,036 / week

The Gold Eagle - Cottage 14

Lake George cottage

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £121 / night

£664 - £726 / week

Hand-Crafted Cottage near Gore Mountain

Minerva cottage

  • Child friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £157 / night

£848 / week

Paradox Lake front luxury home 3200 square foot

Schroon Lake house

  • Child friendly
  • •  Private garden
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £383 / night

£2,678 / week

Viewing 40 of 151
rentals in Chestertown